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Ashland Vacation Rentals

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    Travelers to Ashland are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 53 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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    Hopyard Views Farm - Minutes to Downtown Ashland!1 / 21
    (1)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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Parking
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Note: '1900' Guest House (Next Door) May Also Be Available: (It features a King Bed and Full Kitchen and Bathroom) 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 features...
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    Ashland, Oregon 97520
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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 April 19, 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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 13
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Yard
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just 2 blocks to Downtown Ashland Plaza... and 1 block from OSF make this a perfect getaway! This two-story home has three bedrooms; the master has a king-size bed and the guest rooms each have queen-sized beds. There is a spacious living room with plenty of seating and a sofa-bed. The home can...
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    Ashland, Oregon 97520
    Rental Home - 3 Bedrooms, 2 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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    • Parking
    • Patio
    • Porch
    • Wi-Fi
    • Outdoor Dining Area
    • Mountain Views
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 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 May 8, 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...
    Reviewed March 31, 2015
    An ideal cottage in a country setting, 15 minutes from Oregon Shakespeare Festival. It's the little things that make a big difference to me: friendly, flexible host; comfy bed...
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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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    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
    • Cable/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...
    Reviewed April 16, 2014
    This place is exquisite. Elizabeth and Mark are the quintessential owners who have poured their hearts into creating an oasis that resonates with love and attention to detail...
    Reviewed October 6, 2012
    We've just finished our fourth annual stay at High Street Cottage and we could not be more satisfied. Great location, marvelous grounds, fantastic hosts, great town. Just don't...
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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
    Rental Home - 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 Yard
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 2, 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 July 23, 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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    Ashland, Oregon 97520
    Rental Home - 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
    Rental Home - 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 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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    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • 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
    Rental Home - 2 Bedrooms, 1 Bathroom, 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...
    Reviewed July 23, 2015
    We stayed three days at Lori Lane. There were four of us and it suited us very well. It is walking distance to downtown and the OSF. We ate our breakfasts and a couple of...
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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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    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 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
    Reviewed September 20, 2014
    Our group of four found the cottage super clean and very peaceful. It was quieter than expected with the main road less than a block away and everyone slept well. Air...
    Reviewed June 21, 2013
    Took my senior citizen mother and my brother for their first trip to Ashland. We all thought the cottage was charming. It was well appointed and equipped. the grounds are very...
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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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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 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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    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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    Location Information
    Ashland, Oregon 97520
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Private Yard
    • Air Conditioning
    • Parking
    Suitability
    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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    Location Information
    Ashland, Oregon 97520
    Condo/Apartment - 1 Bathroom, Sleeps 2
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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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    The Cottage at Grizzly Peak Winery - Sleeps 41 / 9
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Parking
    • Mountain Views
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    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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    • 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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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Private Yard
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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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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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 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...
    Reviewed June 22, 2016
    It's not a big place as a matter of fact there are only two cottages. But if your lucky enough to get a reservation here you will not be disappointed. Super clean and fantastic...
    Reviewed March 13, 2016
    Such a beautiful, cozy cottage. Owner was amazing and there were several sweet amenities. Parking was right in front. Beds and bedding were so comfortable and appliances and...
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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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    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • 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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    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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    Location Information
    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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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 Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 13, 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 September 14, 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...
    Reviewed April 18, 2015
    My wife and I stayed for 5 nights and it was an amazingly satisfying experience. Located 15 min from Ashland up a winding road with nice vistas going to and from, it is set in a...
    Reviewed September 21, 2014
    I know everybody says we stayed in an amazing place but you have no idea what amazing really is until you've stayed at the Artycottage!! The owners have made every piece of...
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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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    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    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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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    This color blocked home shows off the beautiful spirit of life in Ashland. Just five blocks away from OSF, this home has a king bed in the upstairs sleeping loft and pull-out sofa 10' queen bed in the living room downstairs to sleep up to 4 people. It has a full kitchen with refrigerator, stove and...
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    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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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    Ashland, Oregon 97520
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    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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    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 - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    (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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    A 1900's Classic Farmhouse REBORN! Red Tail ... Downtown Ashland's Luxury Boutique Inn is NOW OPEN! Enjoy your four block walk to Oregon's Shakespeare Festival as you pass local Coffee Bars, Shops, and Restaurants ~ Furnishings mix Modern Farmhouse, Art Nouveau and feature Local Artist Kay...
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    Ashland, Oregon 97520
    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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    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...
    Reviewed April 26, 2016
    We had family in town and wanted to find a home base close to downtown. 2nd Street Cottages was so much more than a home base! It is a block from downtown, both units have full...
    Reviewed February 18, 2016
    My boyfriend and I stayed at 2nd Street Cottages for a long weekend and were more than pleased with our experience. It is a darling home located within blocks of town and...
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    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Cable/satellite TV
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    Kid friendly
    Smoking allowed
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    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    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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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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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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