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Holiday Homes in Ashland

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    Travellers to Ashland are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    All 97 Rentals in Ashland
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    ArtYcottage  UNBELIEVEABLE...1 / 32
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Walk to Downtown/Theaters from this Charming Home1 / 8
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    The High Street Cottage An Artists' Garden Cottage1 / 10
    (7)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Abigail's Cottage, 10-min. walk to plaza/theaters1 / 20
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Secure Parking
    • Outdoor Dining Area
    • Air Conditioning
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2015
    Beautiful spot, wonderful cottage, perfect for the four of us. Less than a 5 minute drive to down town Ashland with it's fabulous plays, restaurants and shopping. Lovely new...
    Reviewed 7 May 2015
    Abigail's has new owners, who we found to be friendly and helpful. Super clean cottage, walked to plays two times a day. Great time
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    About this property
    Abigail's Cottage within walking distance to the city center, is licensed by the city of Ashland (Business License #007411 & Planning Action #06-275) and Jackson County, (#1581566C) and meets required health, safety and fire codes. Comfortable two bedroom 1 1/2 bath cottage, completely renovated...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Terra Cottage Inn a beautiful Luxury Apartment1 / 10
    (10)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Mountain Views
    • Cable/satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2013
    Terra Cotta Cottage is a beautiful place to stay in Ashland. Every need has been anticipated with artistic thoughtfulness.Staying there was an experience in itself. From the koi...
    Reviewed 12 April 2013
    We thoroughly enjoyed our stay in Terra Cottage Inn. The space was perfect for our family of four with two young children. The beds were comfy for everyone. The whole...
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    About this property
    Nestled into one of Ashland's best neighborhoods, the Terra Cottage Inn is a clean and beautiful, hand-crafted artists' cottage. Full of art, hand thrown pottery, custom built furniture and all the amenities to make this a true luxury experience. Quality comfortable beds with high thread count...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Singing Birds Cabin1 / 15
    (24)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Parking
    • Grill
    • Porch
    • Central Heating
    • Wi-Fi
    • Outdoor Dining Area
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 June 2018
    The owners were very responsive and gave detailed instructions on just about everything, from directions to the cabin to many post-it notes around the cabin. We were welcomed...
    Reviewed 30 July 2017
    My husband and I had the best vacation at this cozy log cabin.The location was perfect.The view from the porch was just wonderful.Every morning of our week there we enjoyed our...
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    About this property
    Beautiful log cabin in the Southern Oregon Cascade Mountains. Located very privately on 160 acres of mountain meadowland. Cabin sleeps up to 6 people, but the only door is on the downstairs bath with sleeping beds in the open loft and also downstairs. Full kitchen, full bath down and half bath...
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    Ashland, Oregon 97520
    Cabin Holiday Rental - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pelton Villa1 / 12
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Patio
    • Washer
    • Parking
    • Private Garden
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2018
    Our family of 4 stayed 2 nights in the Earth Suite because everything else was booked. We would've stayed 3 if it had been available. We walked to OSF, downtown for meals, and...
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    About this property
    Experience Ashland like a local. Pelton Vacation Rental in downtown Ashland is the place to be. We have 3 private units: The Villa main house, Earth suite carriage house, and Water suite carriage house. As a vacation rental, other than having the best location in Ashland, we offer our guests...
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    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just a stone's throw to the plaza, a licensed one-bedroom vacation rental suite is tucked behind one of Ashland's charming craftsman-style bungalows. Your private gated entrance, located behind the house, opens onto a peaceful garden and quaint patio - a wonderful place to enjoy morning coffee and...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Blue Hyacinth in Blossom View Cottages. Walk to downtown and OSF or sit back and relax at the Blue Hyacinth, part of Blossom View Cottages. This is a luxurious and comfortable home in Ashland's historic railroad district. Downtown Ashland, the theaters, and galleries on A-Street are...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Private Garden
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Ashland Lodge Style House w/Patio & 5 MTN Bikes!1 / 31
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Terrace
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • DVD Player
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 April 2017
    Our family thoroughly enjoyed our stay at this stunning vacation cabin located in an area that provided plenty of privacy. The Guest Contact person, Eliasar, who greeted us upon...
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    About this property
    Have a truly memorable trip to Oregon when you stay at this gorgeous 4-bedroom, 3-bathroom Ashland home, which sleeps 13. Enjoy the best of outdoor living with a private fishing pond and plenty of patio space with spectacular views! THE PROPERTY Master Bedroom: King Bed | Master Bedroom 2: King...
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    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 13
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    Stay Ashland like never before.  Explore days, campfire stars at night!1 / 13
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2018
    Anyone in this area needing to rent a trailer should go with this company. They are wonderful. Their trailers are emmaculate and come with everything you need. They went out of...
    Reviewed 16 May 2018
    I loved driving into the campground and finding the trailer and campsite all set up and waiting for us. The trailer was super clean and well stocked with bathroom and kitchen...
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    About this property
    Vacation rental. RV Adventure. You choose favorite RV site in So. Oregon! Trailer camping is where tiny house intersects with camping; the perfect relaxing balance of re-energizing in the great outdoors and snuggling up in cozy cottage comfort! Rent a sweet recreational trailer delivered to the...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    De Launay House1 / 16
    (9)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Patio
    • DVD Player
    • Mountain Views
    • Washer
    • Internet Access
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 September 2014
    This wonderful house is in the perfect location, we never had to use our car. Our apartment was adequate space for the three of us and we all loved the furnishings. Everything...
    Reviewed 4 September 2014
    There are 3 nice suites in the house. The other "suites" are the living room, dining room and a bed between the bed in one suite and the bathroom. We were a family...
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    About this property
    Location & Luxury! Just a block from town and renowned Oregon Shakespeare Festival and.easy walking everywhere. Enjoy this historic Craftsman with fully-equipped kitchenettes, private patios, mountain views, claw-foot soaking tubs, A/C, wireless and all the amenities of home. Beautifully...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
    • Washer
    • Cable/satellite TV
    • Balcony
    • Mountain Views
    • Internet Access
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Second Spring Property We are excited to announce that our property was given The Ashland Historic Preservation Award in 2014. This luxury vacation property is uniquely designed for elegance and comfort that will make you feel right at home. This newly renovated craftsman can be rented as a 3...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Perfect vacation cottage1 / 25
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 3 July 2016
    Perfectly furnished for our party of four adults; perfectly stocked kitchen; perfect front yard for dining al fresco and watching deer go by; perfect neighborhood for daily...
    Reviewed 25 August 2015
    Great location for walking to theatres as well as restaurantsand shopping in Ashland. Great space for two couples tobe separate or to be together. Front porch is a...
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    About this property
    Fully restored vintage cottage in a quiet neighborhood just steps away from downtown Ashland and the theater. Surrounded by lovely gardens assuring a private and serene environment. The cottage is tastefully decorated , is immaculate and has 2 bedrooms, 2 baths, office, full kitchen, front porch...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Porch
    • Grill
    • Wi-Fi
    • Mountain Views
    • Hot Tub
    • Washer
    • Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Meadow House, built in 2000, features natural wood and plaster throughout, a well-stocked cook's kitchen with fresh eggs and milk in the refrigerator, and the quiet of off-grid living. The three bedroom, two bath house sleeps up to ten comfortably with 3 twin beds in the West Bedroom, a queen bed...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    2nd Street Cottages, HERITAGE HOUSE1 / 16
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Balcony
    • Private Garden
    • Air Conditioning
    • DVD Player
    • Terrace
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 April 2017
    I would go back to Ashland just to stay here. Seriously. We were passing through on our way to California and needed somewhere tho spend the night. What a lucky accident! The...
    Reviewed 13 November 2016
    Just enjoyed 5 nights at the 2nd Street Cottages. Everything was perfect. We flew in from the east coast and got in close to midnight but Sugar was there to greet us. She...
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    About this property
    THE HERITAGE SUITE IS A DELIGHTFUL 4 BEDROOM, 3 FULL BATH COTTAGE THAT ACCOMMODATES 8 GUESTS COMFORTABLY. Second Street Cottages is located on a quiet side street in the historic and beautiful Railroad District. Built in 1900, this home has been lovingly restored with great attention to detail...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    Second Spring Property We are excited to announce that our property was given The Ashland Historic Preservation Award in 2014. This luxury vacation property is uniquely designed for elegance and comfort that will make you feel right at home. This newly renovated craftsman can be rented as a 3...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! Welcome to your Hyatt Lake Cabin with direct lake views! The master bedroom has a queen size bed, and the living room has queen sleeper sofa. Full kitchen,...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Hot Tub
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    • Patio
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house is located on our ranch. It is 5 miles from downtown Ashland. It is 3 miles to local airport & 3.5 miles to local golf course. The views of the mountains, pastures, wildlife, cows & horses are very beautiful. It is relaxing and enjoyable. This home has hardwood floors. It is a...
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    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Washer
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Terrace
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully renovated - available May 1st, 2018 It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Originally built in 1904, this historic home is one one of three located on the property. Just one block from the theatre, you’ll also have easy access to dining, wine...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully renovated - available May 2018 It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Originally built in 1904, this historic home is one one of three located on the property. Just one block from the theatre, you’ll also have easy access to dining, wine...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    A high queen bed dominates the space, which gets diffused light from a skylight and windows on three sides. A spacious bathroom features a clawfoot tub, a separate tiled shower, stained glass window and another wonderful skylight. The Carlisle Garden Suites has 9 unique rooms in three buildings...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Parking
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Welcome to your Hyatt Lake Cabin with Hot Tub! The master bedrooms both have a queen size bed, and the sleeping lofts both have two full beds. Full kitchen, dining room, and bathroom. The cabins both have bbqs, decks,...
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    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Private Garden
    • Air Conditioning
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Best Location, Impeccable Style and Ultimate Comfort1 / 17
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 January 2018
    We thought this place was very comfy Cozy. Very Cute, in nice neighborhood. Within walking distance of shops in town. We will definitely recommend and would rent again when...
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    About this property
    Our cottage is where you want to stay in Ashland! From its fantastic location to its custom craftsman design to the overall comfort, you'll be delighted with your choice! Just 3 level blocks from the downtown Ashland Plaza and Shakespeare festival. Along with clean, quality and location,...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    This is the largest room of the suites and has a single bed with trundle as well as a king/twin. Surrounded by mature trees and fragrant jasmine vine, this room offers a palette of Ashland summer sky blues. A kitchenette, walk-in multi-headed luxury shower for two and the deck overlooking a...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Water Suite Cottage is one of the closest properties to OSF, just one and half blocks to the Theaters. The home features a kitchenette, living room with sofa-bed, flat panel 4K TV, one...
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    Location Information
    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Built in the late 1800's, the Sherwin House is in the heart of Ashland and is one of the closest properties to OSF, just one and half blocks to the Theaters. The home features a full kitchen, a front yard with seating, two private...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 11
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    A corner room filled with filtered light from shuttered windows, this room is guarded by two ancient holly trees with red berries. The door opens onto an outside dining area on the deck, enjoyed by all who come. This room also has a kitchenette and a spacious bath with a jetted tub. The Carlisle...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Carlisle Garden Suites - Viola Suite1 / 14
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
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    Reviewed 3 April 2018
    We just spent one night here, but wish we could have stayed longer. It was a lovely spot, 4 blocks from down town Ashland. We stayed in the Camomile Suite, which had a king bed...
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    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Balcony
    • Private Garden
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
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    Location Information
    Ashland, Oregon 97520
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Oak Tower Cottage is one of the closest properties to the famed Oregon Shakespeare Festival, and just one and half blocks to the Theaters. The home features a full kitchen, a patio, two...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    A high ceiling with fan and marvelous light throughout the day give this room a sense of comfort and elegance. Decorated with lavender and turquoise, it has king/twin beds, kitchenette, two-person Jacuzzi tub and opens on to the back deck that overlooks our quiet gardens. The Carlisle Garden...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    7 Bedrooms, 7 Bathrooms, Sleeps 13 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Anne Hathaway House was built in 1908 as a boarding house for travelers. David and Deedie Runkel purchased the home in 2002 and continue to operate it today. Located just four short blocks from the Oregon Shakespeare Festival, the Anne Hathaway House is ideal for large groups of theater goers,...
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    Ashland, Oregon 97520
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 13
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience Ashland like a local. Pelton Vacation Rental in downtown Ashland is the place to be. As a vacation rental, other than having the best location in Ashland, we offer our guests many in-room complimentary amenities. With the intention of making Pelton environmentally friendly, we use...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Private Garden
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    • Outdoor Dining Area
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    • Grill
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a very beautiful modern unique property. Two bedrooms, sitting room/kitchenette all custom designed, Italian fixtures, exquisite cherry wood floors, marble bathroom, wireless internet, cable TV, HBO/ Showtime, central air/heater, and a stunning view of the private back garden. All you...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! Welcome to your Hyatt Lake Cabin with a large deck and Hot Tub! The master bedroom has a queen size bed, and the sleeping loft has two queen beds. Full...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Parking
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and enjoy your stay in this classic, fully restored farmhouse built in 1890. You’ll pass local coffeehouses, boutique shopping, and fantastic restaurants when you stroll just four short blocks to the Oregon Shakespeare Festival theatres. Furnished with an artistic blend of modern farmhouse...
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    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful, historic, fully renovated home with four bedrooms, three full baths and a fabulous welcoming front porch. Can be rented with Garden Suite, a 2 bedroom, 2 full bath house that sleeps five. Perfect location for your visit to Ashland. Historic Railroad District is situated between two...
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    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Built in 2008, this home is adjacent to a historic home and one one of three located on the property. Just one block from the theatre, you’ll also have easy access to dining, wine tasting, and shopping. Private,...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Private Garden
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Balcony
    • Terrace
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Washer
    • Parking
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Parking
    • Wi-Fi
    • Grill
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! Welcome to your PREMIUM Hyatt Lake Cabin with Hot Tub! The master bedroom has a queen size bed, and the sleeping loft has a full and twin bed. Full kitchen,...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    1
    Ashland Holiday Rentals

    Are you looking for the perfect holiday rental in Ashland, Ore.? Then come on in and take a look. Ashland, noted for its postcard picture perfect seasons, beautiful topography and friendly people, is the perfect holiday spot. Now that you’ve found it, you need someplace to stay. Rental cabins are a wonderful option and may be ideal for you and your family. Many are only a hop, skip and a jump from Ashland amenities, while affording you the privacy you desire. Make it a holiday to remember with a rental cottage, condo or cabin. With multiple price points and rental options, you’re sure to find something that fits your budget – and we can help.

    Ashland Activities

    If you’re looking for something to do while you’re in Ashland, head on over to the Oregon Shakespeare Festival. Each season brings something different for Shakespeare lovers ranging from tours to your favorite play. Other cultural events include the Oregon Cabaret Theater and the Ashland Independent Film Festival. Ashland is also home to more than 80 art galleries and multiple museums, such as the ScienceWorks Hands On Museum for children and the Ashland Art Center. From your home away from home holiday rental, plan your day around the activities that suit you best!

    Romancing Ashland

    Of course, with its beautiful location at the base of the Cascade Mountain Range, Ashland is perfect for lovers. Let us help you find a quaint rental cottage for two, while you focus on romance! Wine and dine with the best of them at several area restaurants including Chateaulin French restaurant. Here, you’ll find the perfect ambiance in the intimate and romantic dining room as well as an extensive wine list and gourmet French food. Or try the nationally acclaimed Winchester Restaurant at the Winchester Inn. Take your chocolate loving sweetie to the Oregon Chocolate Festival or go for a bike ride on the Mt. Ashland Mountain Bike Trail.

    Ashland is for Skiing and Golf

    With several mountain ranges in the Southern Oregon area, Ashland is perfect for the ski enthusiast! Hit the slopes at any one of the area resorts with trails ranging from beginner to professional, cross country to downhill. Find a rental cabin with access just outside your door and you’ll be in ski heaven. Located at 7,500 feet, Mt. Ashland offers skiing during the season from November to April on a variety of trails for any skill level as well as snowboarding. Golf resorts include Oak Knoll in Ashland and Centennial Golf Club in nearby Medford.

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