Ashland: Vacation Rental By Owner

Showing 20 Of 128 Vacation Rentals
  • Property-1 Image 1
    House $455 / Nightly
    • 4 Bed
    • 3 Baths
    • (41)
    Ashland, OR

    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... ...more

  • Property-2 Image 1
    House $268 / Nightly
    • 3 Bed
    • 3 Baths
    • (37)
    Ashland, OR

    The Madrone House welcomes you to the Pacific Northwest, tucked at the base of the Cascade and Siskiyou Mountain Ranges. Located on our secluded 40 acres, this... ...more

  • Property-3 Image 1
    Cabin Select Dates for Price
    • 2 Bed
    • 1 Baths
    • (4) Exceptional
    Ashland, OR

    Summary: Located just 18 miles east of downtown Ashland - The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! Welcome to your... ...more

  • Property-4 Image 1
    House $382 / Nightly
    • 3 Bed
    • 2 Baths
    • (75) Excellent
    Ashland, OR

    This 1907 home has been lovingly remodeled with a gorgeous cherry-wood kitchen, custom granite counters, all new kitchen appliances and amenities. The original... ...more

  • Property-5 Image 1
    House Select Dates for Price
    • 2 Bed
    • 2 Baths
    Ashland, OR

    This award winning building is located in Ashland's historic railroad district just 2 blocks from Main Street and 3 blocks to Ashland's Plaza. With a light and... ...more

  • Property-6 Image 1
    Guest House Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (10) Wonderful
    Ashland, OR

    Our studio is comfortably furnished and nestled away in the beautiful Siskiou National Monument. This light filled studio is a perfect retreat for a couple or... ...more

  • Property-7 Image 1
    Townhome Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (19) Wonderful
    Ashland, OR

    The View is a large comfortable flat on the second floor of the 4th St Inn. The View has a living room with gas fire place and comfortable seating, a dining area... ...more

  • Property-8 Image 1
    Cottage $113 / Nightly
    • 1 Bed
    • 1 Baths
    • (52) Wonderful
    Ashland, OR

    Relax and Renew in this private detached ground level Cottage. Oberon has a cozy living & kitchenette that is equipped with everything you need to cook a... ...more

  • Property-9 Image 1
    Cottage Select Dates for Price
    • 2 Bed
    • 1 Baths
    • (3) Exceptional
    Ashland, OR

    Summary: This home is not just pet-friendly, but pet-welcoming. This beautifully restored Farm House is divided into a two suite home a short walk from the Oregon... ...more

  • Property-10 Image 1
    House $145 / Nightly
    • 1 Bed
    • 1 Baths
    • (42) Wonderful
    Ashland, OR

    Available is a private bedroom suite with it's own entrance, bathroom and deck with dining area only 5 blocks from the Shakespeare Festival. The house was built... ...more

  • Property-11 Image 1
    Guest House $219 / Nightly
    • 1 Bed
    • 1 Baths
    • (1) Exceptional
    Ashland, OR

    The John and Charlotte Pelton House was built in 1894 by Ashland builder W. J. Schmidt. By its size and distinction as an example of Eastlake architecture, the... ...more

  • Property-12 Image 1
    Guest House $162 / Nightly
    • 1 Bed
    • 1 Baths
    • (7) Wonderful
    Ashland, OR

    The John and Charlotte Pelton House was built in 1894 by Ashland builder W. J. Schmidt. By its size and distinction as an example of Eastlake architecture, the... ...more

  • Property-13 Image 1
    House $234 / Nightly
    • 3 Bed
    • 2 Baths
    • (3) Exceptional
    Ashland, OR

    Beautiful, large architectural home nestled in the Siskiyou/Cascade mountain forest of Southern Oregon. About 15 minutes to downtown Ashland, 20 minutes to Mt.... ...more

  • Property-14 Image 1
    Guest House $244 / Nightly
    • 2 Bed
    • 2 Baths
    • (47)
    Ashland, OR

    Fabulous Location! This cozy place is only 4 blocks to Downtown. 7 - 10 minute stroll to Oregon Shakespeare Festival Theaters, Plaza & Lithia Park. Relax and... ...more

  • Property-15 Image 1
    House $264 / Nightly
    • 2 Bed
    • 1 Baths
    • (8) Wonderful
    Ashland, OR

    Summary: Fully renovated! It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Originally built in 1904, this historic home is... ...more

  • Property-16 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (16) Exceptional
    Ashland, OR

    Summary: It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Built in 2008, this home is adjacent to a historic home and one... ...more

  • Property-17 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (6) Exceptional
    Ashland, OR

    Summary: Fully renovated! It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Originally built in 1904, this historic home is... ...more

  • Property-18 Image 1
    Cabin Select Dates for Price
    • 2 Bed
    • 1 Baths
    • (2) Exceptional
    Ashland, OR

    Summary: Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! Welcome to... ...more

  • Property-19 Image 1
    Cabin $194 / Nightly
    • 2 Bed
    • 2 Baths
    • (22) Wonderful
    Ashland, OR

    Book an unforgettable natural getaway to 'Greensprings Wildlife Sanctuary,' a 2-bed, 1.5-bath vacation rental on a wildlife sanctuary in Ashland. This... ...more

  • Property-20 Image 1
    Cottage Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (1) Exceptional
    Ashland, OR

    Summary: Located just blocks away from the Oregon Shakespeare Festival theaters downtown, Courtside Cottage is the perfect place to land on your next visit to... ...more

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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.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Ashland. The most expensive month of the next 12 months is in July, where prices hit an average of $65 a night. In June, prices will hit an average low of $175 per night.