
Holiday houses in Ashland
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Ashland
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
0 of 0 items showing
1 of 12 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Ashland holiday rentals
Other great holiday rentals in Ashland
Top Guest favourite

Home in Medford
5 out of 5 average rating, 51 reviewsHome Away From Home
LicaRating, 5 stars3 months ago
We had a great stay, the best vaca rental experience to date. Lovely house, incredibly clean and well maintained, welcoming and comfortable, exactly as described and pictured, and Debbie and James were wonderful hosts. We were in Medford to visit family for the holidays, and the house was a lovely place to relax after a long day of festivities (I love my family, but you know LOL). Thank you so much Debbie and James!
Top Guest favourite

Home in Rogue River
4.93 out of 5 average rating, 58 reviewsLavender Hill
ShawnaRating, 5 stars2 weeks ago
We had a lovely stay at Lavender Hill! Such a beautiful location, and a cozy home, we loved every moment there. Everything was nice and clean, but still felt like a home. It was well stocked and had everything we needed. We're all looking forward to our next family visit so we can stay there again!
Superhost

Home in Central Point
5 out of 5 average rating, 4 reviewsRellik Winery - The Rellik House
AprilRating, 5 stars8 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

Farm stay in Grants Pass
4.58 out of 5 average rating, 43 reviewsElegant Farm
ValarieRating, 5 stars6 months ago
A lovely stay on a beautiful property, with all the amenities you might need. The hot tub right outside the main bedroom was our favorite part. Also loved seeing deer and sheep in the yard. Our host was responsive and friendly. We would recommend!
Guest favourite

Cottage in Central Point
5 out of 5 average rating, 5 reviewsRuby Belle Cottage
ChristinaRating, 5 stars4 months ago
My stay at the Ruby Belle Cottage was nothing short of magical. The space was immaculate and expertly appointed. Everything I could have needed was thought of and provided. Most importantly, the bed is incredibly comfortable and the property is quiet (I slept like a rock!). For a PNW coffee nerd, the espresso machine in the morning was quite the treat. I wish I hadn't been on a tight schedule; otherwise, a leisurely morning with coffee on the patio overlooking the paddocks would have been lovely. I look forward to staying at the cottage again!
Top Guest favourite

Home in Gold Hill
5 out of 5 average rating, 164 reviewsHygge Hideaway. A home for rest and adventure
RoniRating, 5 stars1 week ago
What a perfect getaway for us! Hannah’s cozy home was absolute heaven! Beautiful surroundings, peaceful and clean.
Superhost

Farm stay in Rogue River
5 out of 5 average rating, 4 reviewsGroups 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!
Superhost

Home in Grants Pass
4.83 out of 5 average rating, 291 reviewsDollar Mountain Hideout
Sam & MichelleRating, 5 stars1 week ago
Great spot in Grants Pass for a quick visit. The studio is located in walking distance to town and many store and restaurant options. Quiet neighborhood. Enjoyed soaking in the hot tub watching the stars come out.
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
- Southern Oregon Holiday rentals
- Medford Holiday rentals
- Crescent City Holiday rentals
- Brookings Holiday rentals
- Mount Shasta Holiday rentals
- Crater Lake Holiday rentals
- Grants Pass Holiday rentals
- Klamath Falls Holiday rentals
- Gold Beach Holiday rentals
- Portland Holiday rentals
- Gold Country Holiday rentals
- Northern California Holiday rentals
- Rentals with a patio Ashland
- Rentals with breakfast Ashland
- Family-friendly rentals Ashland
- Rentals with a hot tub Ashland
- Rentals with a fireplace Ashland
- Rentals with a fire pit Ashland
- Rentals with an EV charger Ashland
- House rentals Ashland
- Rentals with outdoor seating Ashland
- Guesthouse rentals Ashland
- Kid-friendly rentals Ashland
- Cottage rentals Ashland
- Cabin rentals Ashland
- Apartment rentals Ashland
- Rentals with pools Ashland
- Private suite rentals Ashland
- Pet-friendly rentals Ashland
- Rentals with a washing machine and dryer Ashland
- Condo rentals Ashland
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom