Ashland vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

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Popular amenities for Ashland vacation rentals

Stay near Ashland's top sights

Lithia Park198 locals recommend
Oregon Shakespeare Festival267 locals recommend
Ashland Springs Hotel3 locals recommend
Ashland's Own Shop'n Kart38 locals recommend
Brickroom76 locals recommend
Ashland Food Co-op91 locals recommend

Ashland house rentals

Guest favorite
Home in Ashland
Coyote Moon
Oct 28 – Nov 4
$200 per night
4.95 out of 5 average rating, 175 reviews
Guest favorite
Home in Ashland
Secluded Forest Log House 15 minutes to Ashland
Nov 25 – Dec 2
$191 per night
4.96 out of 5 average rating, 237 reviews
Guest favorite
Home in Ashland
Ashland Haus Retreat - 1 block from downtown!
Jan 10 – 17
$181 per night
4.91 out of 5 average rating, 190 reviews
Guest favorite
Home in Ashland
High Street Cottage, Artist's Garden Cottage
Nov 20 – 27
$166 per night
4.96 out of 5 average rating, 129 reviews
Guest favorite
Home in Ashland
Casa Bella
Nov 11 – 18
$315 per night
4.95 out of 5 average rating, 103 reviews
Guest favorite
Home in Gold Hill
Rogue River Retreat
Jul 20 – 27
$170 per night
4.99 out of 5 average rating, 209 reviews
Guest favorite
Home in Grants Pass
Gateway to Cathedral hills
Oct 29 – Nov 5
$141 per night
4.97 out of 5 average rating, 282 reviews
Guest favorite
Home in Medford
Southern Oregon Gem (EV Charger)
Aug 22 – 29
$114 per night
4.88 out of 5 average rating, 208 reviews

Other great vacation rentals in Ashland

Guest favorite
Tiny home in Shady Cove
Modern Tiny House w/ Hot Tub
Sep 1 – 8
$118 per night
4.95 out of 5 average rating, 191 reviews
Guest favorite
Cabin in Ashland
Beautiful Barndominium by Howard Prairie Lake
Jul 26 – Aug 2
$158 per night
4.96 out of 5 average rating, 155 reviews
Guest favorite
Camper/RV in Ashland
Cozy camping close to town
Apr 4 – 11
$47 per night
4.88 out of 5 average rating, 909 reviews
Guest favorite
Guesthouse in Ashland
JJ's Loft | Downtown | Large Deck | Kitchenette
Oct 4 – 11
$125 per night
4.94 out of 5 average rating, 109 reviews
Guest favorite
Cottage in Ashland
Victorian Garden Carriage House
Oct 30 – Nov 6
$172 per night
4.97 out of 5 average rating, 419 reviews
Guest favorite
Cottage in Ashland
The Red Dragon House
Sep 22 – 29
$169 per night
4.99 out of 5 average rating, 139 reviews
Guest favorite
Cottage in Ashland
Weisinger Winery Vineyard Cottage
Jan 31 – Feb 7
$225 per night
4.92 out of 5 average rating, 210 reviews
Guest favorite
Guesthouse in Ashland
Modern Airy Retreat - Views, Walk to Everything
Jan 23 – 30
$175 per night
4.94 out of 5 average rating, 117 reviews

Quick stats about vacation rentals in Ashland

Total rentals

280 properties

Rentals with dedicated workspaces

140 properties have a dedicated workspace

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

100 properties allow pets

Family-friendly rentals

100 properties are a good fit for families

Total number of reviews

19K reviews

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Ashland?

    Yes! Work meets play with ease at over 140 vacation rentals in Ashland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Ashland?

    Four-legged friends are welcome in Ashland. Choose from more than 100 vacation rentals for guests traveling with pets.

  • Are there Ashland vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Ashland, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly vacation rentals in Ashland?

    Ashland has more than 100 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in bed and breakfast rentals in Ashland?

    Experience the best of Ashland with our bed and breakfast rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Ashland have wifi?

    Absolutely! We offer over 90 house rentals with wifi in Ashland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Ashland have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Ashland. Enjoy a tailored experience with all the comforts you desire.

  • Do hotel rentals in Ashland have self check-in?

    Absolutely! We offer over 20 hotel rentals with self check-in in Ashland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Ashland have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Ashland. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Ashland?

    Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with self check-in, over 30 homes with a bbq area, over 10 homes with a gym, over 90 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Oregon
  4. Jackson County
  5. Ashland