Guesthouse vacation rentals in Jackson County

Great location, close to wineries and Jacksonville.

We stayed at this beautiful rural barn for two months and absolutely fell in love. It’s the perfect mix of cozy rustic charm and modern comfort—thoughtfully designed, spacious, and peaceful. The barn atmosphere is warm and inviting, with exposed wood and stunning views of the hills and a serene pond just outside. Every sunset felt like a painting, and the quiet was restorative. The interior was super comfortable, with a great bed, well-equipped kitchen, and all the essentials for a long stay. The owners were incredibly kind, responsive, and respectful of our space—true hosts who made us feel welcome from day one. This spot became a home for us, and we genuinely didn’t want to leave. If you’re looking for a peaceful retreat surrounded by beauty, this is it. 10/10.

Such a serene getaway. Trees, birds and falling to sleep with the sliding glass door cracked so I could sleep to the sounds of the river. Tranquil describes it. They also went above and beyond with fall themes in their decorations. What a great place to do Thanksgiving dinner for my daughter and I. We are beyond grateful they shared their lovely home with us.

We love the Wren! Responsive, friendly & flexible hosts, great location, and SO awesome to have a full kitchen set up and laundry! Spacious. Delightfully functional for our longer-term stay.

Always love staying at the cottages. Quiet and comfortable. Clean space with everything we need. Look forward to the next time we get to come back.

This home was in a quiet, stunning neighborhood with a gorgeous view. We got to watch the sunset from bed! All of the furniture was comfy, cozy, clean, and smelled good. Elyse was so responsive and helped us with a question/request right away. The home was in the perfect center of all of the things we wanted to do while we visited, and so close to a cafe/wine tasting room/food truck spot. We were so happy we chose this place for our long weekend get away.

My daughter and I had a wonderful stay at Julie’s cottage. The location was perfect for visiting Ashland. Private and peaceful yet close to downtown. The cottage was immaculate and so comfortable. We would love to come back!

So happy we were able to stay here - this space was perfect for us! Location - A traditional residential neighborhood (quiet and friendly) but also close to amenities. Space - A true home-away-from-home feel (a nicely made bed, full size washer and dryer, bathtub and all the kitchen appliances a well-established home would have) but also somehow felt like a vacation spot. Overall I was impressed at how much this space had to offer while also feeling open and being clutter free.

We enjoyed our stay at the 1910 Orchard cottage. Everything was terrific, Leslie communicated easily and often, we slept comfortably, and the shower was excellent! Thank you for hosting us on our trip to Ashland.

Wonderfully aesthetic cottage, nicely decorated, great layout. Close to shops and restaurants. Friendly host. Will definitely come back while in Ashland.

Excellent and friendly communication EVERYTHING we needed (very well stocked kitchen), best place we've rented in a long time - we travel often and near always airbnb. Will return here, absolutely zero negatives. Thank you so much James :)

We had a wonderful stay at Susan's place. It was comfortable, Clean and Quiet. The patio is a great place to relax and visit>

my stay was wonderful! The bed was really comfortable with nice clean sheets. Sofa is hecka nice with a big tv. relaxing home away from home feel. the owners house is near by but I still had a since of privacy, very welcoming and nice family. Would recommend anyone to stay here given the chance. The shower is also huge. really liked the bathroom.

We enjoyed our stay. Everything was very clean. The host was very attentive with communication.

This cottage is wonderful! It played a big part in making our visit to Ashland extra special. We loved the easy walk to town, quiet & private location, and exceptionally comfortable bed. It's uncluttered, yet had everything we needed...a great place to stay. We hope to be back!

At the End of the Trail on Rogue River was delightful; everything we needed for a relaxing getaway was there. The property was expansive, private and quiet. We loved staying there. Thank you Mare. 😊

The stay with Jennifer was everything we needed and more. The check-in was super easy and included a private entrance. We really enjoyed the location of this bnb because of the nice scenery & peaceful neighborhood. In the mornings there are deer outside and the evenings there is a nice view of the sunset. It was also close to town, only about 10 minutes from the mall. The apartment itself was supplied with everything we needed for 1 month, including toilet paper, paper towels, dishes and silverware, & extra pillows and blankets. The hosts, Jennifer & Russ, were very friendly and helpful when we needed. Thanks for a great stay!

Haley's place was perfect for us and our trip. It is easily walkable to many stores, restaurants, activities downtown. The place was exactly as Haley described and she was very responsive to any questions we had. We would stay here again.

Great place to stay, this is our second time staying there. Very peaceful and quiet. Walkable to excellent restaurants and Margo’s wine shop and tastings, coffee shop and grocery store.

Nice clean and private detached guesthouse in a very quiet neighborhood. House easy to locate and access even in the dark of the night. Host was kind and responsive. We would definitely stay here again.

Thank you for the amazing stay! Was better than expected, host was kind, responsive and accommodating. Was easy to contact and provided helpful information for check in. Next trip to Medford we hope to stay here!

This is a great Airbnb with quick access to downtown Jacksonville. You can walk to everything within minutes. All of the essentials are covered and the bed is amazingly comfortable. We would stay here again without hesitation.

This was our second time staying here. I can’t recommend it enough. The space is clean, with new appliances. beautifully situated, and extremely peaceful and private.

Hi, my stay was quiet and private. The place was clean and was decorated with nice pieces of art snd travel mementos. It had a very nice deck that I wish I had more time to take advantage of.