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Ashland Cottages

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    $195 Average
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    Travelers to Ashland are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    16 Matching Rentals in AshlandView all 58 rentals
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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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    The Terra Cottage Inn a beautiful Luxury Apartment1 / 10
    (10)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Juliet1 / 15
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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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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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Secure Parking
    • Outdoor Dining Area
    • Air Conditioning
    • Shared Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 24, 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 May 6, 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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    Location Information
    Ashland, Oregon 97520
    Rental Home - 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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    Amenities & Details
    • Shared Yard
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 23, 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 August 8, 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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    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    Amenities & Details
    • Sauna
    • DVD Player
    • Washer
    • Mountain Views
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 14, 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 March 7, 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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Amenities & Details
    • 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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    Location Information
    Ashland, Oregon 97520
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 11
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Central Heating
    • Wi-Fi
    • Private Yard
    • 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
    Rental Home - 1 Bedroom, 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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    Amenities & Details
    • Cable/satellite TV
    • Balcony
    • Private Yard
    • Air Conditioning
    • DVD Player
    • Terrace
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 15, 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 November 12, 2016
    Just enjoyed 5 nights at the 2nd Street Cottages. Everything was perfect. We flew in from the east coast and got in close to midnight but Sugar was there to greet us. She...
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    About this property
    THE HERITAGE SUITE IS A DELIGHTFUL 4 BEDROOM, 3 FULL BATH COTTAGE THAT ACCOMMODATES 8 GUESTS COMFORTABLY. Second Street Cottages is located on a quiet side street in the historic and beautiful Railroad District. Built in 1900, this home has been lovingly restored with great attention to detail...
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    Location Information
    Ashland, Oregon 97520
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Perfect vacation cottage1 / 25
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 2, 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 August 24, 2015
    Great location for walking to theatres as well as restaurantsand shopping in Ashland. Great space for two couples tobe separate or to be together. Front porch is a...
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    About this property
    Fully restored vintage cottage in a quiet neighborhood just steps away from downtown Ashland and the theater. Surrounded by lovely gardens assuring a private and serene environment. The cottage is tastefully decorated , is immaculate and has 2 bedrooms, 2 baths, office, full kitchen, front porch...
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    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 2 Bathrooms, 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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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 4, 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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    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Grill
    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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    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    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, 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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    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Private Yard
    • 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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2nd Street Cottages, GARDEN SUITE1 / 11
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Patio
    • Terrace
    • Central Heating
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 31, 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 June 22, 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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    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Patio
    • Internet Access
    • Parking
    • Cable/satellite TV
    • Shared Yard
    • Air Conditioning
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are located in the heart of Ashland. Only 2 blocks from Downtown. Enjoy the open Garden and Great location to all Restaurants, Shops, Theaters and Local Sporting Events. We are 3 blocks from University of Southern Oregon. Full Kitchen, Bedroom/Queen, Wall mounted reading lamps and TV. The...
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    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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