Guesthouse vacation rentals in Ashland

Great location, close to wineries and Jacksonville.

This really is a dream cottage! It’s right on the Rogue River. My dog and I woke up every morning and went down to the river, and it was never the same twice. Incredible birding, and even saw some river otters! Sam’s sculpture adds a lot of fun surprises to the property- you never know what’s going to appear. The bed was very comfortable, and the kitchen has everything you need to feel right at home. Sam and Paula were so kind and welcoming. Can’t recommend it enough!

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!

Thank you Teresa. Enjoyed your quaint cabin space and the grounds/river. Hope to see you again when we slide through this area.

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.

We enjoyed our stay at the Mermaid House while in Ashland . The kitchen was well stocked . We had space to relax inside and out. The neighborhood was sweet to walk through and had easy access to plays, the coop, and restaurants.

The studio is very well appointed with all that you need. The kitchen area has what you need to prepare meals and it is very appealing with nice dishes and a lovely wooden counter and tiled walls. The living area has a nice desk, arm chairs, TV and a dresser. Lighting is very good in each area.There is a tiny patio, whch is fenced in, out the kitchen door where you can sit at a small table in the morning sun and sip your coffee. While the blue cottage is on a bustling street in a residential area, it is set back off the street and feels private. The host, Dennis, is one of the best hosts we have ever had. He is in a league of his own - super friendly and responsive. If you have questions Dennis will get back to you immediately. He is a delight to work with.

Ivan's place was perfect for my purposes in Grant's Pass. Everything was clean and in working order and they seemed to think of everything. Hot tub was nice after a day of hiking. I probably could have cooked as all the things needed were there but ate out at local restaurants after hikes. Chickens are fun and I loved having them and hearing them nearby.

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 :)

We had a wonderful stay! The house was spotless and beautiful, just as pictured. The location can’t be beat, with stunning river views! Host Julie was so friendly and responsive! We would stay here again and again!

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.

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,

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.

Loved this private little place with a comphy bed, nice linens, soaps, shampoo, updated appliances, and sweet touches. This cute place (which was larger than I expected) had all that we needed for our pickleball tournament a few blocks away. We felt very comfortable and private. Natalie reached out with directions and info prior to our arrival and notified me that she had the place ready earlier than the usual check in time if we wanted. The location was perfect and very close to restaurants like the Horney Goat and Tap Rock. Loved our stay!

Super cozy space, just what we needed for our little trip! I’d definitely stay here again.