Guesthouse vacation rentals in Jackson County

Great location, close to wineries and Jacksonville.

By far, this is the best Airbnb that we have stayed in and we have been too many.The cottage is very nice and roomy and the bed is very comfy... My favorite part is the Rogue river which is right by the house and my pup loved it as much as I did. There are wild blackberries and cherry plums by the river that are delicious...Paula and Sam are wonderful hosts and are always available if we need anything which we did not. The internet is fast and the TV works great.They have a cute pup named Willie and she got along great with our joonbug.. Thanks, to both of you for being wonderful hosts and whichever state we end up moving to you all will always be welcome.

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.

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.

Great place to explore Ashland. Loved the deer in the yard. It’s a bit dark to walk home at night but the area feels safe.

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 was not our first time at the cottage. The place is very nice. The bed is comfortable. The little outdoor space is just right. Lots of privacy and so walkable to shops, theaters and park. Also Philip is very responsive if you have any questions or concerns. Hopefully we will be back again.

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!

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.

This was a great place to land for a couple of days in Ashland. The location was within easy walking distance of OSF, restaurants, shops, and both a Safeway and co-op. I really appreciated the access to shared laundry facilities (including detergent, stain remover, etc). One of the members of our party has a severe gluten allergy and the full kitchen made keeping them fed as simple as zipping to the Safeway down the block and cooking for ourselves. The hosts were responsive and immediately addressed an issue with the dishwasher (a replacement is apparently on the way). Would stay here again. The one downside for me was that the unit is essentially in the middle of the parking lot, with windows on three sides (one side facing the main building, one facing a garage, and one facing an active walkway/driveway).Even though the rental was the whole freestanding apartment, it didn't feel particularly private, especially when neighbors walked by. Perhaps not the spot for a romantic getaway!