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House Rentals and Cabins in Ashland, OR

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    Travelers to Ashland are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 9
    5 of 5 stars (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    3.5 of 5 stars (4) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Arbor Studio is a compact, tidy single building just right for one person, very intimate for two.* It's nestled under a grandmother grapevine and looks out into our in-process healing garden. Expect friendly atmosphere, interior cleanliness, bamboo floors, interesting lighting,filtered drinking... View all property information
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    Ashland, Oregon 97520
    1 / 10
    5 of 5 stars (9) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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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... View all property information
    Location Information
    Ashland, Oregon 97520
    5 of 5 stars 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...
    5 of 5 stars 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 apartment...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Private Garden Cottage at Healing Sanctuary. Our charming 2-room Temple cottage offers privacy and spacious comfort. Expect friendly atmosphere, interior cleanliness, bamboo floors, interesting lighting, filtered drinking water, a moderately equipped kitchenette (toaster oven, micro, electric... View all property information
    Location Information
    Ashland, Oregon 97520
    1 / 16
    5 of 5 stars (16) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    WE RESPOND TO ALL INQUIRES WITHIN 4 HOURS AND USUALLY SOONER ! 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... View all property information
    Location Information
    Ashland, Oregon 97520
    5 of 5 stars 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...
    5 of 5 stars 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...
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
    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... View all property information
    Location Information
    Ashland, Oregon 97520
    1 / 15
    5 of 5 stars (19) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Central Heating
    • Wi-Fi
    • Outdoor Dining Area
    • Mountain Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Elder access
    • x
    About this property
    Beautiful log cabin in the Southern Oregon Cascade Mountains. Located very privately on 160 acres of mountain meadowland. Cabin sleeps up to 6 people. Full kitchen, full bath down and half bath up, hard wood floors, wood stove, front porch where you can sit and watch for wildlife. Fresh air,... View all property information
    Location Information
    Ashland, Oregon 97520
    4 of 5 stars Reviewed October 12, 2015
    The owner warned us that the wasps are very active in August and indeed my kids spotted several and freaked out, deciding to spend the rest of their time indoors. Although this...
    5 of 5 stars Reviewed October 14, 2014
    We traveled to Ashland for a family gathering. Without a doubt, our Singing Birds get-away was the highlight of the trip. Accomodations were cozy, fresh and grounding. Thank you...
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Grill
    • Mountain Views
    • Porch
    • Outdoor Dining Area
    • Shared Yard
    • Parking
    • Hot Tub
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    About this property
    STAY Overlooking beautiful meadows, the light filled studio sleeps up to six with two queen beds in the loft rooms and a double sofa-bed downstairs. The Farrmhouse Studio also features a wood stove and a full kitchen stocked with dry goods. On-Farm Store has all our meats, sausages, eggs and milk... View all property information
    Location Information
    Ashland, Oregon 97520
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    1 / 24
    5 of 5 stars (8) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
    • Outdoor Dining Area
    • Air Conditioning
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    • DVD Player
    • Internet Access
    • Mountain Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    About this property
    Cottage, 1 bedroom, 1 bath (Sleeps 2) Country cottage above detached garage less than 10 minutes from downtown but feels like it’s far from the madding crowd. Hiking and biking right out your door. This 500+ sq. ft., new, fully furnished, self-contained, one bedroom apartment is above our... View all property information
    Location Information
    Ashland, Oregon 97520
    5 of 5 stars Reviewed April 21, 2015
    Our hosts, Marty and Michael, have created a wonderfully comfortable and beautiful place to stay. The Treehouse Retreat is just outside the town of Ashland, located next to a...
    5 of 5 stars Reviewed January 4, 2014
    The 'treehouse' was a charming and lovely vacation rental. Everything from a well-functioning, well stocked kitchen with a beautiful view, to the large, private deck and abundant...
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    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • DVD Player
    • Washer
    • Satellite TV
    • Balcony
    • Mountain Views
    • Internet Access
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
    Location Information
    Ashland, Oregon 97520
    1 / 16
    2 of 5 stars (1) Poor
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Wi-Fi
    • Mountain Views
    • Satellite TV
    • Patio
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    • Grill
    • Washer
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    Wonderful Craftsman-style FARMHOUSE built in 1912 and BUNKHOUSE on a working horse ranch just 3 minutes from downtown Ashland, home of the renowned Shakespeare festival and Britt festivals in nearby historic Jacksonville. 'FARMHOUSE' has 4 bedrooms and 2 full baths. All rooms have queen beds for... View all property information
    Location Information
    Ashland, Oregon 97520
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    $195
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    • x
    • x
    • x
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    • Elder access
    • x
    • ?
    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... View all property information
    Location Information
    Ashland, Oregon 97520
    1 / 16
    5 of 5 stars (9) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    $135
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    • Air Conditioning
    • Patio
    • DVD Player
    • Mountain Views
    • Washer
    • Internet Access
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Location & Luxury! Just a block from town and renowned Oregon Shakespeare Festival and.easy walking everywhere. Enjoy this historic Craftsman with fully-equipped kitchenettes, private patios, mountain views, claw-foot soaking tubs, A/C, wireless and all the amenities of home. Beautifully... View all property information
    Location Information
    Ashland, Oregon 97520
    5 of 5 stars Reviewed October 7, 2014
    Delaunay House is a special place in an area that offers so much to those that travel. This romantic historic home welcomes you in and swallows your stress. The attention to...
    5 of 5 stars Reviewed September 17, 2014
    This wonderful house is in the perfect location, we never had to use our car. Our apartment was adequate space for the three of us and we all loved the furnishings. Everything...
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    1 / 25
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $285
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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... View all property information
    Location Information
    Ashland, Oregon 97520
    5 of 5 stars Reviewed August 24, 2015
    Great location for walking to theatres as well as restaurants and shopping in Ashland. Great space for two couples to be separate or to be together. Front porch is a...
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    1 / 11
    4.5 of 5 stars (4) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    $110
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    • Balcony
    • Internet Access
    • Terrace
    • Parking
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    • Outdoor Dining Area
    • Porch
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Lhasa House is a charming studio cottage with unique privacy and its own street entrance. It is located on the perimeter grounds of a vintage house built in 1884. The property's interior gardens are developing into a healing sanctuary (accessible to guests Summer 2014). The owners are yogic... View all property information
    Location Information
    Ashland, Oregon 97520
    4 of 5 stars Reviewed June 13, 2015
    I wanted a place within walking distance to the theaters but not necessarily all the amenities you would get in a hotel or B&B. We planned on eating out and spending time at the...
    5 of 5 stars Reviewed June 4, 2015
    We thoroughly enjoyed Lhasa House at Chakra Garden. It was comfortable and convenient. The gardens were a lovely addition to our stay. With just a 20 minute walk to the plays and...
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    1 / 10
    5 of 5 stars (5) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    $165
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    • Washer
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    • Satellite TV
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    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
    Location Information
    Ashland, Oregon 97520
    5 of 5 stars 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...
    5 of 5 stars 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...
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
    • Private Yard
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
    Location Information
    Ashland, Oregon 97520
    1 / 11
    5 of 5 stars (7) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $185
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    • Satellite TV
    • Shared Yard
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Abigail's Cottage 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. Please note: Rates do not include food service and we do not accommodate pets. Non-smoking, two bedroom 1... View all property information
    Location Information
    Ashland, Oregon 97520
    5 of 5 stars 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...
    5 of 5 stars 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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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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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... View all property information
    Location Information
    Ashland, Oregon 97520
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Air Conditioning
    • Children's Pool
    • DVD Player
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    • Mountain Views
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
    • ?
    • ?
    About this property
    The perfect location for your next family rendezvous, art retreat or special occasion. There are numerous gardens and the park like setting is lush and shady with ample space inside and out you will always find a quiet place to enjoy all the property has to offer. The Property benefits from a hill... View all property information
    Location Information
    Ashland, Oregon 97501
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Mountain Views
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • Smoking allowed
    • Elder access
    • x
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    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... View all property information
    Location Information
    Ashland, Oregon 97520
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
    • Wi-Fi
    • Hot Tub
    • Grill
    • Balcony
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    • Mountain Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
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    • Elder access
    • x
    • x
    About this property
    Mayfield Gardens offers a gorgeous view across Keene Creek Valley, a full kitchen and a spacious deck. This cabin accommodates up to four or more guests. The private bedroom has a king size bed. The enclosed Jacuzzi tub space is just outside the bedroom door. A leather sofa in the living area... View all property information
    Location Information
    Ashland, Oregon 97520
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Private Yard
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Elder access
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    • x
    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... View all property information
    Location Information
    Ashland, Oregon 97520
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    $375
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    • x
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    • x
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    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... View all property information
    Location Information
    Ashland, Oregon 97520
    1 / 12
    5 of 5 stars (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Shared Yard
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    • Satellite TV
    • Mountain Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
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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... View all property information
    Location Information
    Ashland, Oregon 97520
    5 of 5 stars 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...
    5 of 5 stars 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 other...
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    1 / 15
    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
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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... View all property information
    Location Information
    Ashland, Oregon 97520
    4 of 5 stars 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 outdoor...
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    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Amenities & Details
    • Balcony
    • Terrace
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    1 Bedroom 1 Bathroom Sleeps 3 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 bedroom 2 bath home or split into two connecting apartments with kitchens, dining areas and... View all property information
    Location Information
    Ashland, Oregon
    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.