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  • Oberon -Second Spring Property 1-3 Bedroom Luxury

    Ashland, Oregon

    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... ...more

    Beds: 1 Baths: 1 Property type: Apartment (0)
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  • Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In The Heart Of Ashland

    Ashland, Oregon

    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... ...more

    Beds: 1 Baths: 1 Property type: Apartment (0)
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  • The High Street Cottage An Artists' Garden Cottage

    Ashland, Oregon

    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... ...more

    Beds: 2 Baths: 1 Property type: Cottage (7) Exceptional
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  • The Terra Cottage Inn a beautiful Luxury Apartment

    Ashland, Oregon

    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... ...more

    Beds: 2 Baths: 1 Property type: Cottage (10) Exceptional
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  • Singing Birds Cabin

    Ashland, Oregon

    Beautiful log cabin in the Southern Oregon Cascade Mountains. Located very privately on 160 acres of mountain meadowland. Cabin sleeps up to 6 people, but the only door is on the downstairs bath... ...more

    Beds: 2 Baths: 2 Property type: Log Cabin (24) Exceptional
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  • ArtYcottage UNBELIEVEABLE...

    Ashland, Oregon

    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... ...more

    Beds: 2 Baths: 2 Property type: House (19) Exceptional
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  • Farmhouse Studio at Willow Witt Ranch

    Ashland, Oregon

    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... ...more

    Beds: 2 Baths: 1 Property type: House (0)
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  • Meadow House on a Historic Ranch in Ashland, OR

    Ashland, Oregon

    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... ...more

    Beds: 3 Baths: 2 Property type: House (0)
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  • Abigail's Cottage, 10-min. walk to plaza/theaters

    Ashland, Oregon

    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... ...more

    Beds: 2 Baths: 2 Property type: Cottage (7) Exceptional
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  • Perfect vacation cottage

    Ashland, Oregon

    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... ...more

    Beds: 2 Baths: 2 Property type: Cottage (2) Exceptional
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  • Nancy's Garden Cottage The Indigo

    Ashland, Oregon

    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... ...more

    Beds: 1 Baths: 1 Property type: Cottage (0)
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  • Porscha's Hideaway

    Ashland, Oregon

    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... ...more

    Beds: -1 Baths: 1 Property type: Studio (0)
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  • Porscha's Hideaway 2

    Ashland, Oregon

    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,... ...more

    Beds: 2 Baths: 1 Property type: House (0)
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  • Steps to theatres, shopping, dining, nightlife...

    Ashland, Oregon

    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... ...more

    Beds: 4 Baths: 3 Property type: House (0)
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  • Stone's Throw Bungalow - Licensed, Private Garden

    Ashland, Oregon

    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... ...more

    Beds: -1 Baths: 1 Property type: Studio (0)
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  • Luxurious Home near Downtown Ashland and Theaters

    Ashland, Oregon

    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... ...more

    Beds: 3 Baths: 2 Property type: House (0)
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  • Ashland Lodge Style House w/Patio & 5 MTN Bikes!

    Ashland, Oregon

    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... ...more

    Beds: 4 Baths: 3 Property type: House (1) Exceptional
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  • Walk to Downtown/Theaters from this Charming Home

    Ashland, Oregon

    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... ...more

    Beds: 2 Baths: 1 Property type: Cottage (1) Exceptional
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  • Cattle View Ranch House

    Ashland, Oregon

    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 &... ...more

    Beds: 4 Baths: 2 Property type: House (0)
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  • 2nd Street Cottages, GARDEN SUITE

    Ashland, Oregon

    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... ...more

    Beds: 2 Baths: 2 Property type: Cottage (5) Exceptional
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Search result 1 to 20 Of 247

Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Ashland. Many accommodations in Ashland provide "Non Smoking Only", there are 151, or there are 122 of Vacation Rentals in Ashland with a "Pets Not Allowed", there are also 106 with "Children Welcome", which is another great reason to visit Ashland.