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Ashland Cottages

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    Travelers to Ashland are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    33 Matching Rentals in AshlandView all 116 rentals
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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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    Romeo1 / 12
    (2)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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    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
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    • Mountain Views
    • Satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 28, 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 April 11, 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
    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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    • Sauna
    • DVD Player
    • Washer
    • Mountain Views
    • Wi-Fi
    • Patio
    • Air Conditioning
    • 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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    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
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    • Private Yard
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    Pet friendly
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    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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    The High Street Cottage An Artists' Garden Cottage1 / 10
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Porch
    • Satellite TV
    • Patio
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 4, 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 July 10, 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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    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
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    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Central Heating
    • Wi-Fi
    • Private Yard
    • Parking
    • 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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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, 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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    Perfect vacation cottage1 / 25
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    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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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
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    • Wi-Fi
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    • 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) 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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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Internet Access
    • Patio
    • Air Conditioning
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    Pet friendly
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    Smoking allowed
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    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2nd Street Cottages, HERITAGE HOUSE1 / 16
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • 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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    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
    • 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 2 Quick View
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    • Patio
    • Internet Access
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    • 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. <BR>The...
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    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Hot Tub
    • Parking
    • Terrace
    • Patio
    • Grill
    • Air Conditioning
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 1
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Ashland, Oregon 97520 2650
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Ashland, Oregon 97520
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    Ashland, Oregon 97520
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    Ashland, Oregon 97520
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    Ashland, Oregon 97520
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    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Ashland, Oregon 97520
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    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    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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    • Satellite TV
    • Washer
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    • DVD Player
    • Sauna
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    Pet friendly
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    Smoking allowed
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    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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