Guesthouse vacation rentals in Ashland

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.

Absolutely loved staying here! We were greeted by Joe and Nancy! They were so thoughtful and asked if we needed anything from the grocery store. They left an activity box out for our kiddo and even accommodated a late check out. The home was beautiful, but the best part was listening to the river at night while we slept with the windows open. If you’re looking for a great getaway from the city with amazing hosts I 10/10 recommend!

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.

For a solo or couple this place is great. Convenient location, clean, fun, comfortable. Has all the stuff you need - well stocked!

Perfect little spot to stay close to downtown and lots of fun coffee shops/ restaurants nearby. A nice walkable neighborhood as well. Would definitely stay here again!

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 :)

Our stay at the property was wonderful. The house was so clean you could almost eat off the floor. The location on the river was fabulous, so peaceful and lovely we were in awe. You could tell all the thought that went into the creation of the awesome space, everything was considered and top notch. We would stay there again in a heartbeat. Thank you so much for the delightful stay.

We spent the Christmas night there and it was fantastic! The host left a holiday treat for us which really made our day. They were quite responsive and easy to communicate with. This is the place that I will recommend to anyone and choose to stay again should I visit Grants Pass in the future.

We wanted to thank you for being such a fantastic host! The stunning views, cleanliness, and your hospitality was truly a blessing to us. We especially appreciated the comfortable bed and how lovely the house smelled! We would definitely recommend your Airbnb to others!

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.

Carla was wonderful and so helpful. She offered to help me with my dogs and offered a later checkout if I needed. My husband was in the hospital so I was so grateful for her offerings. I highly recommend!

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

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>

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.

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.

Quaint, Quirky and Quiet. Quant - peaceful little cottage on a wooded lot away from town Quirky - the spiral starcase had its own unique charm Quiet - away from the city, all I could hear was the nearby creek, bursts of frogs at night and the wind in the trees. Just the kind of stay I look for,

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

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.

We loved our stay here! This was my first Airbnb experience, and it couldn’t have gone better. This was a lovely little apartment, with all the kitchen supplies you could need, cozy bedding, a washer and dryer, and a nice kitchen bar and couch area to hang out in. Natalie was very communicative and responsive. We’ll definitely stay here again if we are in the area!