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Holiday Homes in Ashland

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    Travellers to Ashland are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    All 93 Rentals in Ashland
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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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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • Balcony
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    • Wi-Fi
    • Washer
    • Terrace
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just 2 blocks to Downtown Ashland Plaza... and 1 block from OSF make this a perfect getaway! This two-story home has three bedrooms; the master has a king-size bed and the guest rooms each have queen-sized beds. There is a spacious living room with plenty of seating and a sofa-bed. The home can...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Parking
    • Cable/satellite TV
    • Wi-Fi
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    Suitability
    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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    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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    Mountain Pine Cabin - Pet Friendly1 / 25
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 3 weeks ago
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Parking
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Note: '1900' Guest House (Next Door) May Also Be Available: (It features a King Bed and Full Kitchen and Bathroom) The Historic '1900' House is the best of Downtown Ashland... and less than five blocks to the renowned Oregon Shakespeare Festival. A quiet residential neighborhood, our home features...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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 3 weeks ago
    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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    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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    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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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Housekeeping Included
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    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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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Parking
    • 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 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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    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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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    • Grill
    • Cable/satellite TV
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    • DVD Player
    • 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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    The Cottage at Grizzly Peak Winery - Sleeps 41 / 9
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
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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 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    RedTail Inn ~ 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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    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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    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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    2 Bedrooms, 2 Bathrooms, 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 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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A 1900's Classic Farmhouse REBORN! Red Tail ... Downtown Ashland's Luxury Boutique Inn Enjoy your four block walk to Oregon's Shakespeare Festival as you pass local Coffee Bars, Shops, and Restaurants Furnishings mix Modern Farmhouse style with Art Nouveau accents. Linens are made in the...
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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 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 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    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 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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    • DVD Player
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    Pet friendly
    Kid friendly
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 15 Quick View
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    • DVD Player
    • Mountain Views
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    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 4 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, 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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    • Patio
    • Washer
    • Air Conditioning
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    • 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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    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 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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    • Parking
    • Central Heating
    • Cable/satellite TV
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    • Grill
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    • Hot Tub
    • Mountain Views
    Suitability
    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, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Balcony
    • Cable/satellite TV
    • Patio
    • Terrace
    • Air Conditioning
    • Housekeeping Included
    • 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 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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    1 Bedroom, 1 Bathroom, Sleeps 4 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 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 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    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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    • Housekeeping Included
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    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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    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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    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 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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    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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    The High Street Cottage An Artists' Garden Cottage1 / 10
    (7)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Porch
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    Pet friendly
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    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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    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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    • Cable/satellite TV
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    • Hot Tub
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    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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    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    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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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Mountain Views
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    About this property
    A 1900's Classic Farmhouse REBORN! Red Tail ... Downtown Ashland's Luxury Boutique Inn (scheduled for completion in Spring 2017) 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...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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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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    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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    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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    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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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    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 - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    616 Fair Oaks Ct. Ground-level condominiums with contemporary flair, these elegant homes are ready for your short or long-term vacation or corporate stay. Located in Meadowbrook Park just a few blocks from North Mountain Park and the Nature Center, these homes are just a short drive from the...
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    Ashland, Oregon 97520
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    • Wi-Fi
    • Private Garden
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    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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    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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