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

Top Guest favourite
Home in Medford
5 out of 5 average rating, 51 reviews

Home 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 reviews

Lavender 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 reviews

Rellik 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 reviews

Elegant 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 reviews

Ruby 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 reviews

Hygge 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 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!
Superhost
Home in Grants Pass
4.83 out of 5 average rating, 291 reviews

Dollar 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

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