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Holiday Homes near Mount Ashland

1745 Ashland St, Ashland, Oregon 97520-2328
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    Travellers to Ashland are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    All 70 Rentals in Ashland
    2.6 kilometres from Mount Ashland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2.2 kilometres from Mount Ashland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3.0 kilometres from Mount Ashland
    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    2.8 kilometres from Mount Ashland
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Hopyard View Farm - Minutes to Downtown Ashland!1 / 25
    (1)Very good
    6.0 kilometres from Mount Ashland
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Private Garden
    • Central Heating
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    • Mountain Views
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 September 2017
    We loved getting a glimpse of the hop harvest in progress just outside our door. Also, the couple that greeted us and lived in attached quarters was friendly and helped us...
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    About this property
    Just a quick five minutes from Downtown Ashland! Views of mountains, sheep, and chickens can be enjoyed from YOUR private deck, with (seasonal) hops, grapes and blackberries growing right outside your bedroom window This spacious modern suite is bright and comfortable, has a private entrance,...
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    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2.6 kilometres from Mount Ashland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Oak Street Cottages ~ Hideaway ~ 1.5 Blocks to Oregon Shakespeare Festival!1 / 9
    (1)Very good
    2.8 kilometres from Mount Ashland
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Oak Street Cottages~Tower Townhouse ~ 1.5 Blocks to Oregon Shakespeare Festival!1 / 9
    (1)Average
    2.8 kilometres from Mount Ashland
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • DVD Player
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    • Grill
    • Balcony
    • Terrace
    • Wi-Fi
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    2.6 kilometres from Mount Ashland
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
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    • 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2.0 kilometres from Mount Ashland
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Housekeeping Included
    • Central Heating
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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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2.0 kilometres from Mount Ashland
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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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 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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    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2.0 kilometres from Mount Ashland
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Abigail's Cottage, 10-min. walk to plaza/theaters1 / 20
    (7)Excellent
    3.6 kilometres from Mount Ashland
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.0 kilometres from Mount Ashland
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.5 kilometres from Mount Ashland
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    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
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Walk to Downtown/Theaters from this Charming Home1 / 8
    (1)Excellent
    2.3 kilometres from Mount Ashland
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
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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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    The Cottage at Grizzly Peak Winery - Sleeps 41 / 9
    (1)Excellent
    3.6 kilometres from Mount Ashland
    1 Bedroom, 1 Bathroom, 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 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2.0 kilometres from Mount Ashland
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Balcony
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    • Housekeeping Included
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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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.8 kilometres from Mount Ashland
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2.0 kilometres from Mount Ashland
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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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 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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2.0 kilometres from Mount Ashland
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Smoking allowed
    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
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Oak Street Cottages ~ Sherwin ~ 1.5 Blocks to Oregon Shakespeare Festival!1 / 12
    (7)Very good
    2.8 kilometres from Mount Ashland
    4 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    • Wi-Fi
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    • Grill
    • Balcony
    Suitability
    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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 11
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    3.0 kilometres from Mount Ashland
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    RedTail Suites ~ The 'Red' McCall Suite ~ Sleeps Six1 / 18
    (1)Excellent
    2.1 kilometres from Mount Ashland
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Mountain Views
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    Pet friendly
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    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2.0 kilometres from Mount Ashland
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Private Garden
    • Washer
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    • Mountain Views
    • Patio
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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
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    3.5 kilometres from Mount Ashland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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'...
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    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3.5 kilometres from Mount Ashland
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5.8 kilometres from Mount Ashland
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1.9 kilometres from Mount Ashland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Smoking allowed
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5.0 kilometres from Mount Ashland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2.2 kilometres from Mount Ashland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1.9 kilometres from Mount Ashland
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Grill
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    • Mountain Views
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    • Wi-Fi
    Suitability
    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
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    The Terra Cottage Inn a beautiful Luxury Apartment1 / 10
    (10)Excellent
    3.5 kilometres from Mount Ashland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    • Internet Access
    • DVD Player
    • Mountain Views
    • Cable/satellite TV
    • Grill
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    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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    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2.0 kilometres from Mount Ashland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2.3 kilometres from Mount Ashland
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    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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    Location Information
    Ashland, Oregon
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    The High Street Cottage An Artists' Garden Cottage1 / 10
    (7)Excellent
    3.5 kilometres from Mount Ashland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Porch
    • Cable/satellite TV
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    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 March 2018
    The columnist Herb Caen wrote of the San Franciscan native who died and went to Heaven. Saint Peter met him at the Pearly Gates and gave him a tour of his new eternal home. When...
    Reviewed 5 March 2016
    My boyfriend and I did "experience" gifts for each other at Christmas and this was mine to him. We loved it! Fantastic craftsman cottage with all the amenities you need...
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    About this property
    Set in Ashland's best neighborhood, this 1931 cottage has been lovingly restored and set up to address your every need. Cozy and incredibly clean, filled with art, hand-made pottery, antiques and hand crafted furniture. Comfortable beds, high quality linens and a fully equipped kitchen. A truly...
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    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2.0 kilometres from Mount Ashland
    1 Bedroom, 1 Bathroom, Sleeps 2 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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    Location Information
    Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    De Launay House1 / 32
    (9)Excellent
    2.7 kilometres from Mount Ashland
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Patio
    • DVD Player
    • Mountain Views
    • Washer
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    • 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
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    3.7 kilometres from Mount Ashland
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    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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    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2.5 kilometres from Mount Ashland
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 days ago
    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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    Location Information
    Ashland, Oregon
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2.0 kilometres from Mount Ashland
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2nd Street Cottages, HERITAGE HOUSE1 / 16
    (5)Excellent
    2.4 kilometres from Mount Ashland
    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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2.4 kilometres from Mount Ashland
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
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    • 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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    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Perfect vacation cottage1 / 25
    (2)Excellent
    3.1 kilometres from Mount Ashland
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.4 kilometres from Mount Ashland
    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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    Location Information
    Ashland, Oregon
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2.0 kilometres from Mount Ashland
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2.0 kilometres from Mount Ashland
    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 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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    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1.8 kilometres from Mount Ashland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Internet Access
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    • Shared Garden
    • Air Conditioning
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are located in the heart of Ashland. Only 2 blocks from Downtown. Enjoy the open Garden and Great location to all Restaurants, Shops, Theaters and Local Sporting Events. We are 3 blocks from University of Southern Oregon. Full Kitchen, Bedroom/Queen, Wall mounted reading lamps and TV. The...
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    Location Information
    Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Carlisle Garden Suites - Viola Suite1 / 14
    (1)Very good
    2.0 kilometres from Mount Ashland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2.0 kilometres from Mount Ashland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Smoking allowed
    About this property
    One of our new luxury suites in the middle of the garden, Iris features a cozy day bed in the sitting room with fireplace and television, as well as a full kitchen and eating area. Dappled light from glass brick windows cascades over the king bed (which can also be twins). Mexican ceramics...
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    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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