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Ashland: Vacation Rental By Owner

Search result 1 to 20 Of 131
  • Property-1 Image 1
    Townhome Select Dates for Price
    • 2Bed
    • 2Baths
    Ashland, OR

    Summary: Cute and colorful, you’ll love this cozy townhouse close to downtown This bright and colorful luxury townhouse has everything you need for... ...more

  • Property-2 Image 1
    House $264 / Nightly
    • 2Bed
    • 1Baths
    • (7) 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... ...more

  • Property-3 Image 1
    House Select Dates for Price
    • 8Bed
    • 5Baths
    Ashland, OR

    Summary: One block from OSF, sleeps 22 guests! It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. This whole... ...more

  • Property-4 Image 1
    Guest House Select Dates for Price
    • 2Bed
    • 1Baths
    • (3) Excellent
    Ashland, OR

    Summary: Completely renovated, and just five blocks from Downtown Ashland and the Oregon Shakespeare Festival! This cottage has two private bedrooms,... ...more

  • Property-5 Image 1
    Cottage Select Dates for Price
    • 2Bed
    • 1Baths
    • (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... ...more

  • Property-6 Image 1
    Cottage Select Dates for Price
    • 1Bed
    • 1Baths
    • (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... ...more

  • Property-7 Image 1
    House $218 / Nightly
    • 1Baths
    • (16) Exceptional
    Ashland, OR

    Summary: 3rd Night Free!!! November 1st through February 29th Some restrictions may apply. To take advantage of this promotion, book 2 nights and... ...more

  • Property-8 Image 1
    Apartment Select Dates for Price
    • 2Bed
    • 1Baths
    • (6) Wonderful
    Ashland, OR

    Summary: High above the hamlet of Ashland sits Bel Canto, a quiet home nestled in the hillside with stunning views of the charming town below. This... ...more

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

    Summary: 3rd Night Free!!! January 6th through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply. To take advantage... ...more

  • Property-10 Image 1
    Cabin Select Dates for Price
    • 4Bed
    • 2Baths
    • (1) Exceptional
    Ashland, OR

    Summary: 3rd Night Free!!! January 6th through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply. To take advantage... ...more

  • Property-11 Image 1
    Cabin Select Dates for Price
    • 2Bed
    • 1Baths
    • (4) Exceptional
    Ashland, OR

    Summary: 3rd Night Free!!! January 6th through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply. To take advantage... ...more

  • Property-12 Image 1
    Cabin Select Dates for Price
    • 4Bed
    • 2Baths
    • (5) Wonderful
    Ashland, OR

    Summary: 3rd Night Free!!! January 6th through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply. To take advantage... ...more

  • Property-13 Image 1
    Cabin Select Dates for Price
    • 4Bed
    • 2Baths
    Ashland, OR

    Summary: 3rd Night Free!!! January 6th through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply. To take advantage... ...more

  • Property-14 Image 1
    Cabin Select Dates for Price
    • 2Bed
    • 1Baths
    • (22) Excellent
    Ashland, OR

    Summary: 3rd Night Free!!! January 6th through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply. To take advantage... ...more

  • Property-15 Image 1
    Cabin Select Dates for Price
    • 2Bed
    • 1Baths
    • (13) Very Good
    Ashland, OR

    Summary: 3rd Night Free!!! January 6th through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply. To take advantage... ...more

  • Property-16 Image 1
    House Select Dates for Price
    • 6Bed
    • 6Baths
    Ashland, OR

    Just five blocks from the Oregon Shakespeare Festival in a historic Ashland neighborhood... Built in the early 1900's and fully renovated the Blue Moon House has... ...more

  • Property-17 Image 1
    Cottage Select Dates for Price
    • 6Bed
    • 6Baths
    Ashland, OR

    Property Location Located in Ashland, this cottage is within a 15-minute walk of Allen Elizabethan Theatre and Angus Bowmer Theatre. This cottage is 0.6 mi (1... ...more

  • Property-18 Image 1
    Cottage Select Dates for Price
    • 2Bed
    • 1Baths
    Ashland, OR

    Property Location With a stay at this cottage in Ashland (Historic Downtown District), you'll be within a 5-minute walk of Allen Elizabethan Theatre and Angus... ...more

  • Property-19 Image 1
    House Select Dates for Price
    • 1Bed
    • 1Baths
    Ashland, OR

    Property Location Located in Ashland, this vacation home is within a 15-minute walk of Allen Elizabethan Theatre and Angus Bowmer Theatre. This vacation home is... ...more

  • Property-20 Image 1
    Cottage Select Dates for Price
    • 2Bed
    • 1Baths
    Ashland, OR

    Property Location With a stay at this cottage in Ashland (Siskiyou-Hargadine Historic District), you'll be steps from Ashland Library and 6 minutes by foot from... ...more

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 January, where prices hit an average of $18 a night. In December, prices will hit an average low of $0 per night.