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Holiday Rentals in Ashland

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    Travellers to Ashland are booking July dates now. Secure your holiday home today, and have the perfect trip.
    All 72 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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    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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    Oak Street Cottages ~ Sherwin ~ 1.5 Blocks to Oregon Shakespeare Festival!1 / 12
    (6)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
    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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    • 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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    Hopyard View Farm - Minutes to Downtown Ashland!1 / 25
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Private Garden
    • Central Heating
    • Parking
    • 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 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • Grill
    • Cable/satellite TV
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Oak 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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    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
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Balcony
    • Terrace
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    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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    (#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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    • 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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    • Cable/satellite TV
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Parking
    • Cable/satellite TV
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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 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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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    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, microwave, and Keurig coffee maker are also available for your comfort. The courtyard is beautifully furnished and has a beautiful shared...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bathroom, Sleeps 2
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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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    Abigail's Cottage, 10-min. walk to plaza/theaters1 / 20
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Secure Parking
    • Outdoor Dining Area
    • Air Conditioning
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 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 6 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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    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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Parking
    • Cable/satellite TV
    • Mountain Views
    Suitability
    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 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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    • 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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    Singing Birds Cabin1 / 15
    (23)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 29 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...
    Reviewed 26 July 2016
    We had a great time at the Singing Birds. The weather was perfect, which helped, and we enjoyed the seclusion of the location along with the comfort of the rustic cabin. Kind...
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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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    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Cable/satellite TV
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    • Patio
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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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    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
    COMING THIS SPRING! 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...
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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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    • Patio
    • Washer
    • Air Conditioning
    • Parking
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    COMING THIS SPRING! 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...
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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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    • Parking
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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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    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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    • Mountain Views
    • Air Conditioning
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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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Cable/satellite TV
    • Central Heating
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    • Grill
    • Mountain Views
    • DVD Player
    Suitability
    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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    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 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
    • Wi-Fi
    • Grill
    • DVD Player
    • 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, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    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'...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 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
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    Pet friendly
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    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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    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 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Mountain Views
    • Cable/satellite TV
    • Air Conditioning
    • Terrace
    • Balcony
    • Wi-Fi
    • Secure Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 15 Quick View
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    • DVD Player
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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
    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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    Location Information
    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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    • Parking
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    • Patio
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    Kid friendly
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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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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Mountain Views
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    • Central Heating
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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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    4BR Ashland Lodge Style House w/Patio!1 / 31
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Terrace
    • Washer
    • Skiing: Property Is In A Ski Resort
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 April 2017
    Our family thoroughly enjoyed our stay at this stunning vacation cabin located in an area that provided plenty of privacy. The Guest Contact person, Eliasar, who greeted us upon...
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    About this property
    Have a truly memorable trip to Oregon when you stay at this gorgeous 4-bedroom, 3-bathroom Ashland home, which sleeps 13. Enjoy the best of outdoor living with a private fishing pond and plenty of patio space with spectacular views! THE PROPERTY This Ashland vacation rental home is an ideal...
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    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 13
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    ArtYcottage  UNBELIEVEABLE...1 / 16
    (17)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2016
    We had a remarkable time here as we celebrated grandma's 80th birthday with 3 generations of daughters. The pictures did not prepare us for the utter beauty of the cottage and...
    Reviewed 15 September 2015
    What really sets this cottage apart from many you may have rented is that the owners have hand crafted and built every inch of the inside and outside. It is artistry and...
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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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    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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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 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 4 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 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
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    About this property
    Welcome to the Blue Hyacinth in Blossom View Cottages. Walk to downtown and OSF or sit back and relax at the Blue Hyacinth, part of Blossom View Cottages. This is a luxurious and comfortable home in Ashland's historic railroad district. Downtown Ashland, the theaters, and galleries on A-Street are...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    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 97520
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2nd Street Cottages, HERITAGE HOUSE1 / 16
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Balcony
    • Private Garden
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    • DVD Player
    • Terrace
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    • 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 12 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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    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Porch
    • Grill
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    • Hot Tub
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    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Meadow House, built in 2000, features natural wood and plaster throughout, a well-stocked cook's kitchen with fresh eggs and milk in the refrigerator, and the quiet of off-grid living. The three bedroom, two bath house sleeps up to ten comfortably with 3 twin beds in the West Bedroom, a queen bed...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    The Terra Cottage Inn a beautiful Luxury Apartment1 / 10
    (10)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Air Conditioning
    • Internet Access
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    • Mountain Views
    • Cable/satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 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 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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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
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    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house is located on our ranch. It is 5 miles from downtown Ashland. It is 3 miles to local airport & 3.5 miles to local golf course. The views of the mountains, pastures, wildlife, cows & horses are very beautiful. It is relaxing and enjoyable. This home has hardwood floors. It is a...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
    • Washer
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    • Patio
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Second Spring Property We are excited to announce that our property was given The Ashland Historic Preservation Award in 2014. This luxury vacation property is uniquely designed for elegance and comfort that will make you feel right at home. This newly renovated craftsman can be rented as a 3...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    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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