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Holiday Homes in Ashland

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    Travellers to Ashland are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    All 92 Rentals in Ashland
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Hopyard View Farm - Minutes to Downtown Ashland!1 / 25
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    ArtYcottage  UNBELIEVEABLE...1 / 16
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2018
    My friend and I stayed at the Arty Cottage for 3 nights while visiting the Shakespeare festival in Ashland. The Cottage itself was a delight to stay in, with amazing woodwork...
    Reviewed 4 July 2018
    Staying at Arty Cottage is like living within a work of art. My family and I have stayed here on two different occasions. Both times we marvelled at the workmanship of the...
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    About this property
    Welcome to the Artycottage nestled in the Cascade foothills, minutes from downtown Ashland, Oregon, home of the Oregon Shakespeare Festival and Saydah Design. All of the work in the Artycottage is made by Saydah Design and can be ordered. Come stay for a weekend or a week and experience...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Cable/satellite TV
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just five blocks from the Oregon Shakespeare Festival in a historic Ashland neighborhood... Built in the early 1900's and fully renovated the Blue Moon House has it all! Five bedrooms, each with it's own private bathroom. A gourmet kitchen with a large dining area, a living area with a fireplace,...
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    Ashland, Oregon 97520
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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    Oak Street Cottages~Tower Townhouse ~ 1.5 Blocks to Oregon Shakespeare Festival!1 / 9
    (1)Average
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • DVD Player
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    • Grill
    • Balcony
    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 May 2018
    Loved the location of this vacation rental. Convenient to everything and they allow dogs. We enjoyed sitting outside and eating dinner and watching the wild deer come through...
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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, Oak Tower Townhouse is one of the closest properties to the famed Oregon Shakespeare Festival, and just one and half blocks to the entry of the Theaters. The home features a full kitchen, a...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Oak Street Cottages ~ Hideaway ~ 1.5 Blocks to Oregon Shakespeare Festival!1 / 9
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 23 May 2018
    This place is ideally situated for what Ashland has to offer. Theater and several good restaurants within 4 or 5 blocks. Lithia Park a couple of blocks further, and from there...
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    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) The home features a full kitchen, generous living room with fireplace, flat panel television, a patio with BBQ and seating, two private bedrooms, full bathroom, and enough sleeping space to accommodate up to 6 guests. The cottage...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    (#52) Hyatt Lake Cabin ~ Sleeps 4 ~ Direct Lake View1 / 24
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    • Central Heating
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2018
    I just loved this cabin with everything else around it. we went there in Dec when it snowed and we loved it. Beautiful drive from Ashland, with lots of beautiful sceneries to...
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    About this property
    Views of Hyatt Lake, the Steel Trestle Bridge, the surrounding Alpine Forest... and just eighteen miles from downtown Ashland! Outside, the Huge Covered Deck has a Double Hammock and Outdoor Dining! Inside the Sleeping Loft has a Queen Bed. The Living Room has a Queen Sectional Sleeper Sofa and 40'...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
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    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 Lawn Cottage is one of the closest properties to the famed Oregon Shakespeare Festival, at just one and half blocks to the entry of the Theaters. The home features a full kitchen,...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • Parking
    • Cable/satellite TV
    • Mountain Views
    • DVD Player
    • Central Heating
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Eighteen miles east of downtown Ashland... Just a three minute walk to Hyatt Lake, your cabin has a new hot tub and a huge deck overlooking the forest... with pocket views of Mount Ashland! The bedroom has a queen bed, and the loft has two full beds. There is a full kitchen, sectional sofa, futon,...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Mountain Pine Cabin - Pet Friendly1 / 25
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2018
    This Cabin was beautiful! It was out in the woods (which my husband loved) but inside had all the things I needed. Ha!TV, Dish, WIFI, washer and dryer!But you still felt like...
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    About this property
    NEW! You've just found your mountain dream...and just 20 miles from downtown Ashland! Mountain Pine Cabin sits on a wooded acre of land, with views of Hyatt Lake from the deck and dining room. Your home features a full kitchen, great room with a sofa and love seat, as well as a 55' Smart TV, WiFi,...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Hot Tub
    • Patio
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just eighteen miles east of Ashland and POCKET VIEWS OF HYATT LAKE! Welcome to your Hyatt Lake Cabin, with a BBQ, and a large deck overlooking the forest, and pocket views of Hyatt Lake. It's just a few minute walk down to the water! The master bedroom has a queen size bed, and the loft has two...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    RedTail Suites ~ The 'Red' McCall Suite ~ Sleeps Six1 / 18
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Mountain Views
    • Parking
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 May 2018
    Absolutely love this place!! The rooms were super inviting, clean and comfy (especially the bed!). The owners thought of everything (even stocking the place with great local...
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    About this property
    A 1900's Classic Farmhouse REBORN! Red Tail ... Downtown Ashland's Luxury Boutique Inn is NOW OPEN! Enjoy your four block walk to Oregon's Shakespeare Festival as you pass local Coffee Bars, Shops, and Restaurants ~ Furnishings mix Modern Farmhouse, Art Nouveau and feature Local Artist Kay...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Cable/satellite TV
    • Central Heating
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Eighteen miles east of downtown Ashland and just a three minute walk to the lake... Your cabin has a hot tub and a deck overlooking the forest... with pocket views of Mount Ashland! The bedroom has a queen bed, and the loft has both full and single beds. There is a full kitchen, sofa, chair, a...
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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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    • Patio
    • Washer
    • Air Conditioning
    • Parking
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home has being fully renovated...from the studs out... with all new furnishings! This is the closest vacation home to the Oregon Shakespeare Festival. Only one full block separates the house from the main entrance to the theaters. There are two private bedrooms, both with king beds, and a...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This single level, two bedroom flat is furnished and decorated with upscale contemporary style. At 1243 sq. ft., the space includes two king size beds made right here in the Pacific Northwest, two bathrooms, washer, and dryer. The living room also has a comfortable queen size sofa bed which means...
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    Ashland, Oregon 97520
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hyatt Lake Cabin Home! 1.5 acres and close access to the lake. Just 5 minutes from the Hyatt Lake Resort, the Pacific Crest Trail and the Table Mountain Winter Play Area! Two story, three bedrooms (master downstairs / upstairs dormitory style), one and one half baths, hardwood flooring, large...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    • Wi-Fi
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2018
    The location was terrific and close to downtown but very quiet and peaceful. The home was lovely, well done and plenty of space for our group. We loved the porch!!! All the...
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    About this property
    Welcome to the Victorian Rose at Blossom View Cottages. We are located in the historic railroad district, less than half a mile from theaters, Plaza and Downtown. Let this charming, historic home fill you with a sense of well-being and luxury. There are two bedrooms, each with a queen bed, and a...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • Wi-Fi
    • DVD Player
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    • Central Heating
    • Mountain Views
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Eighteen Miles East of Ashland... *This Cabin has a twin next door Just a three minute walk to Hyatt Lake, this cabin has a hot tub and a large deck overlooking the forest! The master bedroom has a queen bed, and the loft has two full beds. There is a full kitchen, a new bbq, and one full bathroom....
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Mountain Views
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Patio
    • Waterfront
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just eighteen miles east of Ashland and the LARGEST CABIN AT HYATT LAKE! Just a three minute walk to Hyatt Lake, with a covered Hot tub, and a huge deck overlooking the forest, and pocket views of Hyatt Lake. It's just a few minute walk down to the water! The master bedroom has a queen size...
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    Ashland, Oregon 97520
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This single level, two bedroom flat is furnished and decorated with upscale contemporary style. At 1053 sq. ft., the space includes 2 king size beds made right here in the Pacific Northwest, two bathrooms, washer, and dryer. The living room also has a comfortable queen size sofa bed which means...
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    Ashland, Oregon 97520
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home has being fully renovated...from the studs out... with all new furnishings! This is the closest vacation home to the Oregon Shakespeare Festival. Only one full block separates the house from the main entrance to the theaters. This spacious three bedroom historic home has been fully...
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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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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    This single level, two bedroom flat is furnished and decorated with upscale contemporary style. At 1133 sq. ft., the space includes two king size beds made right here in the Pacific Northwest, two bathrooms, washer, and dryer. The living room also has a comfortable queen size sofa bed which means...
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    Ashland, Oregon 97520
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    This single level, two bedroom flat is furnished and decorated with upscale contemporary style. At 759 sq. ft., the space includes 1 king size and 1 queen size bed, both made right here in the Pacific Northwest, as well as one bathroom, washer, and dryer. The living room also has a comfortable...
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    Ashland, Oregon 97520
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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
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    • Mountain Views
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    • 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 Cottage at Grizzly Peak Winery - Sleeps 41 / 9
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 5 August 2017
    What a sweet location, parklike grounds, vineyard, winery and wonderful welcoming hosts. Virginia & Al made us feel right at home. The cottage is clean, comfortable and...
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    About this property
    Enjoy a free bottle of wine... let us know, red or white... and free admission to one of our summertime concerts (if it coincides with your stay). Nestled on the slopes of Grizzly Peak, less than ten minutes from Downtown Ashland sits our second floor studio cottage! Our second-floor studio...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Oak Street Cottages ~ Sherwin ~ 1.5 Blocks to Oregon Shakespeare Festival!1 / 12
    (7)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2018
    Stayed in the Oak Lawn Cottage – very clean, well appointed, comfy furniture, good parking, good a/c, and fairly quiet except some occasional street noise from Lithia Way, which...
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    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Built in the late 1800's, the Sherwin House is located in the heart of Downtown Ashland and is one of the closest properties to the famed Oregon Shakespeare Festival, at just one and half blocks to the entry of the Theaters....
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    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 11
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Built in the late 1800s, the Sherwin House is located in the heart of downtown Ashland, just one and a half blocks from the famed Oregon Shakespeare Festival. The perfect choice for large groups and those looking to park the car and enjoy an Ashland getaway on foot. The Space Located at the...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    PRIVATE ENTRY AND PARKING The single, private bedroom has a queen bed and private bathroom with shower. Flat-panel TV, with free cable and wi-fi. A mini-fridge and microwave are also available for your comfort. The courtyard is beautifully furnished and has a beautiful shared secret garden for...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Housekeeping Included
    • Central Heating
    • Washer
    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This single level, one bedroom flat is furnished and decorated with upscale contemporary style. At 594 sq. ft., the space includes 1 king size bed made right here in the Pacific Northwest, one bathroom, washer, and dryer. The living room also has a comfortable queen size sofa bed which means this...
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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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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This single level, two bedroom flat is furnished and decorated with upscale contemporary style. At 758 sq. ft., the space includes 1 queen size bed and a twin sleeper sofa made right here in the Pacific Northwest, one bathroom, washer, and dryer. The living room also has a comfortable queen size...
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    Location Information
    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
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    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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    The Blue Moon Cottage is attached to the main home but has two private entrances. It offers a full kitchen, a gas fireplace, air conditioning, a separate bedroom with a comfy queen bed, a full bath with shower/tub combination and a private patio. There is also a flat screen television in the living...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    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 - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    High above the hamlet of Ashland sits Bel Canto, a quiet home nestled in the hillside with stunning views of the charming town below. This immaculate space is situated on the lower level of the owner's home with private entry. Although you’ll feel a million miles away in this peaceful sanctuary,...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    About this property
    Completely renovated, and just a half dozen blocks from Downtown Ashland and the Oregon Shakespeare Festival! This cottage has two private bedrooms, with a queen bed in each. The bathroom has an oversize walk-in shower, great for those with physical limitations. The common area features a 32'...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    NEW and PROFESSIONALLY DESIGNED! Tucked in Downtown Ashland's Historic Railroad District and just a ten to fifteen minute walk to the Oregon Shakespeare Festival. 'C' Street Station is new... from the ground up! This studio home features a luxurious king bed, fireplace, flat screen smart TV,...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Art & Garden Cottage Located in the east Ashland countryside, and exactly three miles from the downtown Ashland Plaza and infamous Oregon Shakespeare Festival, this cottage has it all! The mountain views are stunning and the gardens alive with color in the spring and summer. Enjoy the whimsy and...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    About this property
    This single level, one bedroom flat is furnished and decorated with upscale contemporary style. At 638 sq. ft., the space includes 1 king size bed made right here in the Pacific Northwest, one bathroom, washer, and dryer. The living room also has a comfortable queen size sofa bed which means this...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This single level, two bedroom flat is furnished and decorated with upscale contemporary style. At 971 sq. ft., the space includes 1 queen size bed and 1 king made right here in the Pacific Northwest, two bathrooms, washer, and dryer. The living room also has a comfortable queen size sofa bed which...
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    Ashland, Oregon 97527
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Smoking allowed
    About this property
    Just eighteen miles east of Ashland! Welcome to your Hyatt Lake Cabin! The master bedroom has a queen size bed, and the living room has a sectional sofa to sleep an extra guest. Full kitchen, dining room, and bathroom. The cabin has an (electric) wood stove, 'smart' tv, dvd player, satellite tv,...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    About this property
    The Historic '1900' Guest House is the best of Downtown Ashland! Close to restaurants and retailers... and less than five blocks to the Oregon Shakespeare Festival. In a quiet residential neighborhood, our home features a bedroom with king size bed, a bathroom (shower), a complete kitchen with...
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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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    • Hot Tub
    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Where the Southwest meets the Northwest... Views of Hyatt Lake, the Steel Trestle Bridge, the surrounding Alpine Forest... and just eighteen miles from downtown Ashland! **Enjoy the New Hot Tub** The Master Bedroom has a Queen Bed. The Sleeping Loft has a Queen Bed and Full Bed. The Living...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated, and just a half dozen blocks from Downtown Ashland and the Oregon Shakespeare Festival! This cottage has two private bedrooms, with a queen bed in each. The bathroom has an oversize walk-in shower, great for those with physical limitations. The common area features a 32' flat...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 15 Quick View
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    • Housekeeping Included
    • Hot Tub
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    Smoking allowed
    About this property
    3 story chalet nestled in the Cascade Mountains at 4000' elevation. Fantastic view overlooking Siskiyou Mtns, Klamath Mtns, Colestine Valley and Mt. Ashland. Awesome sunsets! Perfect for hikers, bikers (dozens of trails from Mt. Ashland down to city of Ashland), skiers (Mt. Ashland Lodge is 15...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 15
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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 4 Quick View
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    Each Hyatt Lake cabin comes with wireless internet access, flat panel satellite TV, private deck, and lakefront or forest views. If you choose to dine out, The GreenSprings Inn is close by and offers dining and entertainment throughout much of the year. Looking for watercraft rentals? Let us know...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    De Launay House1 / 16
    (9)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
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    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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    Ashland, Oregon 97520
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Mountain Views
    • Parking
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *This Cabin has a twin next door Eighteen Miles East of Ashland and just a three minute walk to Hyatt Lake, this cabin has a hot tub and a large deck overlooking the forest. The master bedroom has a queen bed, and the loft has two full beds. There is a full kitchen, a new bbq, and one full...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Singing Birds Cabin1 / 15
    (24)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Porch
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    • 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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    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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