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Ashland House Rentals

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    ₹ 29,818 Average
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    Travellers to Ashland are booking June dates now. Secure your holiday home today, and have the perfect trip.
    22 Matching Rentals in AshlandView all 100 rentals
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    7 Bedrooms, 6 Bathrooms, Sleeps 15 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Patio
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    About this property
    Relax and enjoy your stay in this classic, fully restored farmhouse built in 1890. You’ll pass local coffeehouses, boutique shopping, and fantastic restaurants when you stroll just four short blocks to the Oregon Shakespeare Festival theatres. Furnished with an artistic blend of modern farmhouse...
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    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    7 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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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 - 7 Bedrooms, 7 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    About this property
    3rd Night Free!!! November 5th through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply 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...
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    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Built in 2008, this home is adjacent to a historic home and one one of three located on the property. Just one block from the theatre, you’ll also have easy access to dining, wine tasting, and shopping. Private,...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    3rd Night Free!!! November 5th through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply 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...
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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
    • Cable/satellite TV
    • Balcony
    • Washer
    • Mountain Views
    • Terrace
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sleeps 6 - Tesla Charging Station Relax and enjoy your stay in this classic, fully restored farmhouse built in 1890. You’ll pass local coffeehouses, boutique shopping, and fantastic restaurants when you stroll just four short blocks to the Oregon Shakespeare Festival theatres. Furnished with an...
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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 11 Quick View
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    • Air Conditioning
    • Grill
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    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 in the heart of Ashland and is one of the closest properties to OSF, just one and half blocks to the Theaters. The home features a full kitchen, a front yard with seating, two private...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 11
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    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Wi-Fi
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    Pet friendly
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    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...
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    Ashland, Oregon 97520
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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    ArtYcottage  UNBELIEVEABLE...1 / 16
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    • Mountain Views
    • Grill
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 July 2018
    My friend and I stayed at the Arty Cottage for 3 nights while visiting the Shakespeare festival in Ashland. The Cottage itself was a delight to stay in, with amazing woodwork...
    Reviewed 4 July 2018
    Staying at Arty Cottage is like living within a work of art. My family and I have stayed here on two different occasions. Both times we marvelled at the workmanship of the...
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    About this property
    Welcome to the Artycottage nestled in the Cascade foothills, minutes from downtown Ashland, Oregon, home of the Oregon Shakespeare Festival and Saydah Design. All of the work in the Artycottage is made by Saydah Design and can be ordered. Come stay for a weekend or a week and experience...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Blue Hyacinth in Blossom View Cottages. Walk to downtown and OSF or sit back and relax at the Blue Hyacinth, part of Blossom View Cottages. This is a luxurious and comfortable home in Ashland's historic railroad district. Downtown Ashland, the theaters, and galleries on A-Street are...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Ashland Lodge Style House w/Patio & 5 MTN Bikes!1 / 31
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Terrace
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • DVD Player
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 April 2017
    Our family thoroughly enjoyed our stay at this stunning vacation cabin located in an area that provided plenty of privacy. The Guest Contact person, Eliasar, who greeted us upon...
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    About this property
    Have a truly memorable trip to Oregon when you stay at this gorgeous 4-bedroom, 3-bathroom Ashland home, which sleeps 13. Enjoy the best of outdoor living with a private fishing pond and plenty of patio space with spectacular views! THE PROPERTY Master Bedroom: King Bed | Master Bedroom 2: King...
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    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 13
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    Pelton Villa1 / 12
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Patio
    • Washer
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    • Private Garden
    • Air Conditioning
    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2018
    Our family of 4 stayed 2 nights in the Earth Suite because everything else was booked. We would've stayed 3 if it had been available. We walked to OSF, downtown for meals, and...
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    About this property
    Experience Ashland like a local. Pelton Vacation Rental in downtown Ashland is the place to be. We have 3 private units: The Villa main house, Earth suite carriage house, and Water suite carriage house. As a vacation rental, other than having the best location in Ashland, we offer our guests...
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    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Porch
    • Grill
    • Wi-Fi
    • Mountain Views
    • Hot Tub
    • Washer
    • Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Meadow House, built in 2000, features natural wood and plaster throughout, a well-stocked cook's kitchen with fresh eggs and milk in the refrigerator, and the quiet of off-grid living. The three bedroom, two bath house sleeps up to ten comfortably with 3 twin beds in the West Bedroom, a queen bed...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Washer
    • Patio
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house is located on our ranch. It is 5 miles from downtown Ashland. It is 3 miles to local airport & 3.5 miles to local golf course. The views of the mountains, pastures, wildlife, cows & horses are very beautiful. It is relaxing and enjoyable. This home has hardwood floors. It is a...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Mountain Views
    • Porch
    • Outdoor Dining Area
    • Shared Garden
    • Parking
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    STAY Overlooking beautiful meadows, the light filled studio sleeps up to six with two queen beds in the loft rooms and a double sofa-bed downstairs. The Farrmhouse Studio also features a wood stove and a full kitchen stocked with dry goods. On-Farm Store has all our meats, sausages, eggs and milk...
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    Location Information
    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
    • Private Garden
    • Wi-Fi
    • Outdoor Dining Area
    • Parking
    • Grill
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a very beautiful modern unique property. Two bedrooms, sitting room/kitchenette all custom designed, Italian fixtures, exquisite cherry wood floors, marble bathroom, wireless internet, cable TV, HBO/ Showtime, central air/heater, and a stunning view of the private back garden. All you...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Parking
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    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 97520
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Sauna
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Emigrant Creek Guest Lodge above Emigrant Lake. Gorgeous views and water sourced from volcanic healing mineral springs where mountains adjoin volcanism. Nearby are mineral hot/cold springs used by Native people to treat and for ceremonies. Very restorative. The Lodge water has been...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Best Location, Impeccable Style and Ultimate Comfort1 / 17
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2018
    We thought this place was very comfy Cozy. Very Cute, in nice neighborhood. Within walking distance of shops in town. We will definitely recommend and would rent again when...
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    About this property
    Our cottage is where you want to stay in Ashland! From its fantastic location to its custom craftsman design to the overall comfort, you'll be delighted with your choice! Just 3 level blocks from the downtown Ashland Plaza and Shakespeare festival. Along with clean, quality and location,...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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