Ashland vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.
0 of 0 items showing
1 of 3 pages
0 of 0 items showing
1 of 12 pages

Popular amenities for Ashland vacation rentals

Stay near Ashland's top sights

Oregon Shakespeare Festival266 locals recommend
Lithia Park198 locals recommend
Ashland Food Co-op91 locals recommend
Brickroom76 locals recommend
Varsity Theatre56 locals recommend
Standing Stone Brewing Company54 locals recommend

Ashland house rentals

Superhost

Home in Medford

4.92 out of 5 average rating, 103 reviews

Hillcrest Estates

GarthRating, 5 stars3 months ago
We really enjoyed our stay at Robert & Ida's. The house was well kept and comfortable. The beds were comfy, bathrooms clean, and the neighborhood was nice. It's also a plus that they let us bring our two small dogs (for the responsible pet owners). Robert & Ida were very responsive to an questions we had. We would definitely look into staying there again if the occasion arises.
Guest favorite

Home in Medford

4.94 out of 5 average rating, 323 reviews

Clean, pet friendly, 2-Bedroom Cottage with yard.

CarrieRating, 5 stars1 week ago
Always a great stay- this is my preferred Airbnb when I’m in town. Comfortable, pet-friendly. Accommodating and responsive host.
Guest favorite

Home in Gold Hill

5 out of 5 average rating, 150 reviews

Hygge Hideaway. A home for rest and adventure

HannahRating, 5 stars1 week ago
Stepping into the Hygge Hideaway felt like receiving a warm hug. The space was immaculate, serene, and thoughtfully curated. Hanna and Mark communicated well from the start, making our arrival seamless. They truly thought of everything — from the guidebook with personalised recommendations to vintage board games and soft, warm lighting. The eclectic interiors offered cozy seating areas, perfect for relaxing. Natural light filled the space, beautifully complementing the surroundings. We were immersed in nature — squirrels, deer, wild turkeys, and birdsong were constant delights. The deck was ideal for a sundowner, with peaceful views of wildlife. Its proximity to wineries, Ashland, Rogue River hikes, and Crater Lake made it a fantastic base for exploring. It was the perfect cozy end to our Autumnal Oregon road trip. One of the most wonderful Airbnbs I’ve stayed in, with real care taken to ensure an unforgettable experience. Thank you for delivering on the Hygge promise! 🤎🍂🐻☕️
Guest favorite

Home in Grants Pass

4.96 out of 5 average rating, 162 reviews

Heron House King Bed Views

JadeRating, 5 stars4 days ago
Jennifer was so quick to respond and very helpful. The home was prettier in person than in the photos! Very clean! Would highly recommend!
Guest favorite

Home in Ashland

4.93 out of 5 average rating, 14 reviews

Downtown Delight: Ashland's Walkable Retreat

CindyRating, 5 stars3 months ago
Loved the location! The smaller apartments were actually bigger than I imagined and well appointed!
Superhost

Home in Medford

4.84 out of 5 average rating, 232 reviews

Trailer parking, king bed, great for guests/pets!

TrevorRating, 5 stars2 months ago
It was just what we needed. Worked out great.
Guest favorite

Home in Medford

4.89 out of 5 average rating, 203 reviews

Cheerful new 2 bedroom home in cul de sac Netflix

AmyRating, 5 stars2 weeks ago
We loved the little cottage. It was perfect for two hikers looking for a comfortable bed and shower. The Netflix did not work, however, we didn’t bother to reach out about it. I wrote it out on a text after we left but not sure if it went to the housekeeper or Blain. I do think checkout should be 11 an and not 10 and you could most definitely add another fry pan. Otherwise we would definitely return and recommend.
Guest favorite

Home in Central Point

4.91 out of 5 average rating, 121 reviews

Lovely Central Point Home w/EV Charger

ArthurRating, 5 stars2 weeks ago
stayed here for a whole week. the house was perfect, has a big yard with covered patio, quiet nneighborhood. overall great.

Other great vacation rentals in Ashland

Guest favorite

Home in Grants Pass

4.95 out of 5 average rating, 64 reviews

Modern Mountain Getaway

InnovativeRating, 5 stars2 weeks ago
Awesome people. Highly recommended.
Guest favorite

Home in Medford

5 out of 5 average rating, 47 reviews

Home Away From Home

MichelleRating, 5 stars3 days ago
Thank you so much Deborah and James! This is the second time my sister and I have stayed at your place and we love it so much. The dog toys and treats and human snacks and water are all so welcoming and cute to see when we walk in. I loved the Halloween toy for him this time! We are looking forward to booking again soon.
Superhost

Home in Central Point

5 out of 5 average rating, 4 reviews

Rellik Winery - The Rellik House

AprilRating, 5 stars3 months ago
This is such a beautiful home. The setting in the winery is an added bonus. Peaceful, relaxing and refreshing. We rented the entire house and it worked out well. There is the common room but also we had our separate bedrooms to retreat to whenever we wanted. The host was extremely helpful, kind, and responsive. The staff at the winery were extremely friendly as well. The pool and hot tub were clean and easy to use. There wasn’t one bad thing about this place. It is set up perfectly for a family to enjoy a nice home. Even without renting the entire house you still feel like you’re the only one there. Such an enjoyable experience. Will definitely stay here time and time again. Thank you to Valisatie for being such a wonderful host. The house and property are beautiful.
Superhost

Home in Jacksonville

4.91 out of 5 average rating, 33 reviews

Cottage : 1925

NikiRating, 5 stars1 month ago
Nice little cottage, great location, very private, fenced yard! We needed a fenced yard because of our two dogs. The cottage is in walking distance from downtown Jacksonville. Jacksonville is a great small town with good restaurants, a good vibe and several unique stores. The cottage was clean and had a well stocked kitchen if you wanted to cook there, which we didn't. It had a good sized living room, dining room and two adequate bedrooms. Pretty small bathrooms but adequate and clean. We would stay there again!
Guest favorite

Home in Medford

4.88 out of 5 average rating, 26 reviews

I love this house!

ShelbyRating, 5 stars3 weeks ago
Loved this home! The yard was incredible, rooms a decent size, kitchen was beautiful. Our family loved gathering here, and will absolutely stay again when in Medford again!
Superhost

Farm stay in Rogue River

5 out of 5 average rating, 4 reviews

Groups Galore - 2 Spaces Retreat

MariaRating, 5 stars2 months ago
We absolutely loved our stay, thank you for the wonderful hospitality. The location is stunning, and so peaceful. We booked both apartments and it was perfect for our two families. The kids had a wonderful time in the beautiful pool every day. The farm fresh eggs and delicious coffee were a really lovely touch. The owners weren’t there but the biggest shout out goes to the groundskeeper who made our trip unforgettable. He went above and beyond, taking us to feed their pig and chickens, and showing us around the property. Thank you so much for all of the help during our stay!! Would definitely recommend and we’re hoping to be back!
Superhost

Home in Grants Pass

4.82 out of 5 average rating, 272 reviews

Dollar Mountain Hideout

BriceRating, 5 stars1 week ago
Awesome little spot!
Guest favorite

Guesthouse in Grants Pass

4.96 out of 5 average rating, 164 reviews

Chalet in the Woods

AshleyRating, 5 stars3 days ago
My family and I had a great stay at Angela’s chalet. It was close enough to town, yet secluded and away from the hustle and bustle. The hot tub was the perfect way for my husband and I to end a busy day.

Quick stats about vacation rentals in Ashland

  • Total rentals

    340 properties

  • Total number of reviews

    22K reviews

  • Family-friendly rentals

    120 properties are a good fit for families

  • Pet-friendly rentals

    110 properties allow pets

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

Frequently Asked Questions

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

    Yes! Work meets play with ease at over 180 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 110 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 120 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in private suite rentals in Ashland?

    Experience the best of Ashland with our private suite rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do guesthouse rentals in Ashland have wifi?

    Absolutely! We offer over 20 guesthouse 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 house rentals in Ashland have self check-in?

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

  • Do cottage rentals in Ashland have a bbq area?

    Absolutely! We offer over 10 cottage 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 30 homes with a bbq area, over 30 homes with self check-in, over 100 homes with wifi, over 10 homes with a gym, 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