Holiday houses in Ashland

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Popular amenities for Ashland holiday rentals

Stay near Ashland's top sights

Oregon Shakespeare Festival267 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

Other great holiday rentals in Ashland

Guest favourite
Home in Medford
4.92 out of 5 average rating, 38 reviews

Valley Top Private Oasis

CynRating, 5 stars4 months ago
The guest house was extremely quiet and private. It is situated in a safe and beautiful area. The host is very helpful. The inside of the house was clean and comfortable. We hope to rent again.
Guest favourite
Home in Eagle Point
5 out of 5 average rating, 17 reviews

Eagle Point Getaway - Horse & Pet friendly

Chris And TamiRating, 5 stars2 weeks ago
We LOVED this place! The views from the house are gorgeous, and the house itself is clean and comfortable. The house is well supplied with everything guests might need (plenty of pots and pans, spices, additional towels and linens, laundry soap, etc.), as well as "extras," such as DVDs, games, and wood for the wood stove. We were delighted with the wild turkeys, deer, and beautiful flowers on the property, and we enjoyed seeing and hearing the cows in the distance. The incredible beauty and peacefulness of this home is wonderful therapy for the soul! Dorothy was a responsive and gracious host, and we hope to stay at her place again. This home is a 10/10!
Superhost
Home in Central Point
5 out of 5 average rating, 4 reviews

Rellik Winery - The Rellik House

AprilRating, 5 stars9 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.
Guest favourite
Home in Jacksonville
4.89 out of 5 average rating, 90 reviews

Jacksonville Mountain Retreat!

TeresaRating, 5 stars4 weeks ago
Diana‘s place was immaculate. More beautiful than the photos surrounded by nature. The hot tub was awesome since it rained for our stay. Plenty of space for an entire family. I want to come back and have my family in Oregon stay with us there too. We really felt like we were at a mountain retreat. With the small town of Jacksonville just a few miles away. We had a really fantastic time.
Top Guest favourite
Home in Gold Hill
5 out of 5 average rating, 165 reviews

Hygge Hideaway. A home for rest and adventure

NicoleRating, 5 stars1 week ago
Hygge Hideaway was the perfect home for a low-key weekend full of relaxation, the home is decorated intentionally and SO cozy! Close to a few great wineries and enough places to eat without having to go far. Home with fully stocked with anything you could need to cook at home, the three of us had room to spread out and enjoy a beautiful tranquil spring weekend. We will be back if ever in the area again!
Guest favourite
Cabin in Ashland
5 out of 5 average rating, 16 reviews

Whispering Pines Cabin near Hyatt Lake

LaurieRating, 5 stars1 week ago
This is absolutely a gem accommodation especially if you are looking for a quiet, cabin-like feel, in the woods. The drive from Ashland was beautiful and we saw some wildlife. The cabin was perfect for our 2 families. The kids stayed upstairs in the loft area and the adults could have some quiet time on the main floor. The furniture was clean and comfortable. The patio was perfect for the early morning coffee while we waited for the kids to wake up. The host had fun puzzles and games that we enjoyed; we had brought a folding table. Having access to the garage was great so we could pack the cars without getting shoes dirty. We didn't have any issues but thought it would be good to mention. There is only 1 shower at this location. We made it work with 10 people taking quick showers & some of us had our own towels. The drive in is on a dirt road that had large puddles and over time they could get worse - our Subaru did ok.
Superhost
Home in Gold Hill
4.81 out of 5 average rating, 86 reviews

New - Down By The Rogue River - With Fire Pit

RachelRating, 5 stars3 weeks ago
The perfect sanctuary, we especially loved morning yoga on the patio, taking a dip in the river, hanging by the firepit. Great use of space, perfect for a small group of friends coming together and wanting to reconnect with nature. Can’t wait to come back!
Superhost
Farm stay in Rogue River
5 out of 5 average rating, 4 reviews

Groups Galore - 2 Spaces Retreat

MariaRating, 5 stars8 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!

Quick stats about holiday 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

    130 properties allow pets

  • Rentals with a pool

    30 properties have a pool

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

Destinations to explore

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