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Ashland Vacation Rentals

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    Travellers to Ashland are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    All 52 Rentals in Ashland
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    Singing Birds Cabin1 / 15
    (23)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    The High Street Cottage An Artists' Garden Cottage1 / 10
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Porch
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 10 July 2014
    The High Street Cottage is our new favorite place to stay in Ashland. The cottage and grounds were beautifully maintained and thoughtfully stocked with coffee, tea, cooking...
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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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    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
    • Porch
    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. The...
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    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 11
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    Perfect vacation cottage1 / 25
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2016
    Perfectly furnished for our party of four adults; perfectly stocked kitchen; perfect front yard for dining al fresco and watching deer go by; perfect neighborhood for daily...
    Reviewed 24 August 2015
    Great location for walking to theatres as well as restaurantsand shopping in Ashland. Great space for two couples tobe separate or to be together. Front porch is a...
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    About this property
    Fully restored vintage cottage in a quiet neighborhood just steps away from downtown Ashland and the theater. Surrounded by lovely gardens assuring a private and serene environment. The cottage is tastefully decorated , is immaculate and has 2 bedrooms, 2 baths, office, full kitchen, front porch...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, 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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    Romeo1 / 12
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Garden
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 September 2017
    We enjoyed our stay. Dermot is charming, and the location is very convenient walking distance to downtown. Our friends rented the Juliet cottage next door, and it was nice to...
    Reviewed 8 August 2015
    We have been staying at this property once a year for over 10 years, and we can hardly wait to return the next year. This rental and it's adjacent cottage are beautifully...
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    About this property
    Newly remodeled for modern comfort, the Lori Lane Cottages are only a short walk from the Oregon Shakespeare Festival (OSF) and downtown Ashland, where you can experience world class shopping and fantastic local restaurants. Guests have access to private off-street parking and fully stocked...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    • Waterfront
    • Parking
    • Balcony
    • Washer
    • Air Conditioning
    • DVD Player
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 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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    Hopyard Views Farm - Minutes to Downtown Ashland!1 / 21
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Garden
    • Central Heating
    • Parking
    • Mountain Views
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 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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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Juliet1 / 15
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Garden
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2017
    The accommodations were well equipped. The beds were very comfortable and we enjoyed sitting on the patio in the mornings and reading or drawing.
    Reviewed 23 July 2014
    I took my 86 year old mother with me to visit Ashland. The cottage was very clean and cozy and my mom was delighted. There is no real living or dining space inside but the...
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    About this property
    Newly remodeled for modern comfort, the Lori Lane Cottages are only a short walk from the Oregon Shakespeare Festival (OSF) and downtown Ashland, where you can experience world class shopping and fantastic local restaurants. Guests have access to private off-street parking and fully stocked...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
    • Air Conditioning
    • DVD Player
    • Terrace
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 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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    Country Cottage Apartment1 / 23
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Patio
    • Porch
    • Wi-Fi
    • Outdoor Dining Area
    • Mountain Views
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    This lovely cottage is absolutely perfect! It is clean, airy, and tastefully decorated. As you enter the cottage into the living room, you already feel how beautiful...
    Reviewed 8 May 2016
    This cozy cottage in a ranch setting was also a nice getaway from town. Organic eggs, local bread, butter and jam supplied by our host made us feel welcome and provided...
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    About this property
    Private cottage apartment with full kitchen and living area adjacent to family home. Covered porch and garden area to enjoy. Less than 15 minutes to Shakespeare Festival and downtown Ashland. Fresh eggs, local bread, jam, 1/2 and 1/2, milk and butter are stocked in fridge. There is also Nespresso,...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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
    • Air Conditioning
    • Mountain Views
    • Grill
    • Private Garden
    Suitability
    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 14 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 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
    • DVD Player
    • 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 11 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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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    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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    Private and Luxurious Cottage Constructed in 2015 with High End Amenities1 / 26
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Sauna
    • DVD Player
    • Washer
    • Mountain Views
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2017
    I felt welcome in the cottage as the owners greeted me upon arrival and took the time to show me around, explained how things worked, and even offered me a chilled bottle of...
    Reviewed 7 March 2017
    Great location within walking distance to cute little coffee houses and restaurants!! Love the historical neighborhood. Owners went to such detail when building this beautiful...
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    About this property
    Award winning ultra modern luxury cottage located on nearly a half acre estate 3-4 blocks from Ashland Plaza, Lithia Park and the Oregon Shakespeare Festival grounds. The cottage was built in 2015 directly behind the historic Leeke-Mills house build in 1885 and completely renovated in 2007. Ashland...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
    • DVD Player
    • Patio
    • Wi-Fi
    • Waterfront
    • Hot Tub
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years 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...
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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 4 Quick View
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    • Central Heating
    • Parking
    • Mountain Views
    • Patio
    • Balcony
    • Wi-Fi
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tastefully nestled into the hills of Ashland, in a quiet country setting, 2 miles from downtown. The stone villa is an uniquely designed solar home, with abundant entertaining space both inside and out. There are two large, lovely view bedrooms, one upstairs, one downstairs. Each has a private...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
    • Washer
    • Cable/satellite TV
    • Balcony
    • Mountain Views
    • Internet Access
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Second Spring Property We are excited to announce that our property was given The Ashland Historic Preservation Award in 2014. This luxury vacation property is uniquely designed for elegance and comfort that will make you feel right at home. This newly renovated craftsman can be rented as a 3...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Private Garden
    • Air Conditioning
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    Pet friendly
    Kid friendly
    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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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bathroom, Sleeps 2
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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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    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
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years 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...
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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 6 Quick View
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    • Central Heating
    • DVD Player
    • Grill
    • Hot Tub
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years 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...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Second Spring Property We are excited to announce that our property was given The Ashland Historic Preservation Award in 2014. This luxury vacation property is uniquely designed for elegance and comfort that will make you feel right at home. This newly renovated craftsman can be rented as a 3...
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    Location Information
    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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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, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Parking
    • Air Conditioning
    Suitability
    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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    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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    • 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
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years 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...
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    Location Information
    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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    • Central Heating
    • Wi-Fi
    • Private Garden
    • Parking
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the East Ashland countryside, and exactly three miles from the famous Downtown Ashland Plaza and Oregon Shakespeare Festival, our cottage has it all! Enjoy the gardens, the mountain views, and the artwork of local Artist, Michael Gibson. Enjoy the Art and Gardens of one of Ashland's...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Parking
    • Shared Garden
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our property is located in the quaint Shakespearean town of Ashland, Oregon. The town has exceptional and award winning contemporary plays and the largest Shakespearean theater in the United States. We offer boating, hiking trails throughout the area. We have wineries that offer award winning...
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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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    Pet friendly
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    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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    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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    (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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    The Cottage at Grizzly Peak Winery - Sleeps 41 / 9
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 4 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! A 600sqft+ studio cottage...
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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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    • Private Garden
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    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years 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!...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Wi-Fi
    • Terrace
    • Balcony
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    Smoking allowed
    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Oak 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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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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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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2nd Street Cottages, GARDEN SUITE1 / 11
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
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    Reviewed 31 March 2017
    My wife and I stayed in the small apartment on the second floor for a few nights. Sugar met us when we arrived and made the whole transaction very simple for us. The room was...
    Reviewed 22 June 2016
    Lovely cottage with tons of character located in downtown Ashland. We walked just a couple of short blocks to the theater and restaurants. Ours was a spacious, upstairs room...
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    About this property
    THE GARDEN SUITE IS A CHARMING TWO BEDROOM, 2 FULL BATH COTTAGE THAT COMFORTABLY WELCOMES 5 GUESTS. 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 and has...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Patio
    • Mountain Views
    • Hot Tub
    • Washer
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    Pet friendly
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    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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    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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    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Hideaway 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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    • Grill
    • Mountain Views
    • Porch
    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    STAY <BR>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...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    PROMOTION AVAILABLE THROUGH APRIL 2017! BLACK OUT DATES INCLUDE THANKSGIVING WEEK, CHRISTMAS WEEK THROUGH NEW YEARS, AND VALENTINE'S DAY. 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...
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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 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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    High above the hamlet of Ashland sits Bel Canto, your bungalow with views of the surrounding city and the east mountainside. The property features two private bedrooms, with a queen and full. The large living and dining area feature a sectional sofa and flat panel television. There is also a...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years 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...
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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
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    • Hot Tub
    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years 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!...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    • Cable/satellite TV
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years *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...
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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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    PRIVATE ENTRY AND PARKING As long time Owners of a Bed&Breakfast, our 'Butler's Quarters' features one bedroom (queen bed) and a private bathroom (shower). The room has a flat panel television, cable tv, wireless internet, refrigerator, microwave, and Keurig coffee maker. There is a beautiful...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    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
    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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    • Grill
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    • Central Heating
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years 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...
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    Ashland, Oregon 97520
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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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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    Ashland Vacation Rentals

    Are you looking for the perfect vacation 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 vacation 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 vacation 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 vacation 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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