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!

Michelle was such a great host with great communication, and very understanding. I would book again if in oregon!

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!

This was a lovely stay for a girls weekend! The weather was gorgeous and we spent a fair amount of our time outside at the pool and the lawn looking out onto the river. There was a wedding at a location across the river so we got to have lovely background music while we chatted. Literally the PERFECT weekend for us!

Had an excellent stay here. Would absolutely stay again. Space was just right. Excellent hosts!

Had a great stay here! Jim was a very welcoming host who accommodated a last minute stay. The place was very comfortable, and Jim gave very clear instructions that I appreciated

Julie's cottage fit our needs perfectly. Casita Sirena is charming - comfortable, bright, colorful, and decorated with whimsical mermaid-themed artwork. We were a 15 minute walk from the theaters, town center, and Lithia Park. When we weren't walking in the park or attending plays (GREAT selection of plays this spring!), we enjoyed reading on the front porch. There was a binder in the cottage with restaurant and activity recommendations, and very clear instructions for how to use the heat and A/C and what to do when checking out. Julie was great at communicating with us, and responded promptly to messages. Our stay was wonderful!

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.

Staying at Ivan's this past week was exactly what my little family and I needed! We live in Grants Pass but, we love to do little getaways/staycation. His studio and propert were beautiful, quiet and, peaceful. Loved watching the chickens and babies. Definitely recommend for a staycation or if you're from out of town this is an amazing little Airbnb.

Perfect for our needs. Comfortable and convenient location. Very nicely furnished. Great bargain too.

As advertised! Hanna’s house was in a terrific location (VERY walkable to all the things, but tucked away enough that I heard no noise at night), and every thoughtful detail accompanied this Airbnb. Loved it.

The cottage and the property are idyllic and the owners (Nicole and Fernando) are wonderful. They are friendly, accessible, responsive and just about everything you'd want or expect from the host. All of the amenities were as shown and advertised. The only "negatives" were (1) the fact that this a country property means lots of flying and crawling insects, and (2) the property is in a remote country setting. If you're looking for a quiet, relaxing place to unwind, this spot is a gem. If you're interested in a convenient place to stay while enjoying social experiences (dining, theater, shopping, etc.), be prepared to drive a bit.

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>

We had a great stay at this AirBnb. The location was convenient (near family). The place was clean and relatively baby/toddler friendly. I liked the separate room for kids so that we could still be up a bit once we put the our kid down. The bed was comfortable, and everything seemed new and very clean. They’ve thought of just about everything you could need in the kitchen, bathroom, etc. One thing to note is that check in is a little later and check out is earlier than typical so plan for that. Our only issue was a chicken coop outside and a rooster crowing at odd hours (11pm, 4am, etc) waking our family up. I recommend bringing a sound machine or the host adding a purifier or something to drown that out. Overall, we thought this place was lovely and will likely stay here when we visit family again!

Carl’s place was even better than what is described on the website. It is a slice of heaven, a beautiful home away from home, a paradise oasis. Carl went out of this way to make sure I thought right is extremely generous. Thx, Carl

Bryanna's place is spotless, very beautifully decorated and spacious. There were all the amenities that are shown in the photos. She was friendly, flexible, and responsive about checkin. Very minor, but the bed pillows were extremely flat and the twin beds not the most comfortable. All in all a great stay, if a bit pricey for the area.

Great stay with a beautiful private pool and hot tub. Finishes inside were top notch - gave me ideas for my own kitchen. Potential guests should know the bedroom is upstairs while the bathroom is on the main floor down a flight of wooden stairs - something to keep in mind if you have balance issues in the middle of the night. A lovely place for a getaway in Medford.

This rental was nicer looking then the photos - tastefully decorated and nice large rooms. The river view was amazing. We enjoyed watching the ducks and geese float in the river while having a glass of wine on the patio. The neighborhood is not fancy, but the house and view are very nice. We walked to the Rivers' Edge restaurant and enjoyed that as well - lovely view and patio with good food.

This little barn is fixed up so nice. The bed was very comfortable and the place was quiet and secure. I loved all the extra touches..fresh eggs! It is more beautiful than the photos and super clean.

This is our second time staying at Angelica's cozy home, and I know it won't be our last. We have a soccer tournament every year in Rouge Valley and Angelica's house is the perfect location for all the games, and is the perfect spot for relaxation between the busy tournament schedule. The house is cozy and has everything you need. Angelica is a great host. She is responsive and we look forward to future stays.

This was our second stay at Natalie’s cottage and it was as wonderful as the first stay. The cottage is lovely, very private and right in town. We enjoyed every minute of our stay and look forward to our next visit.

The owners were kind respectful and easy to work with. I would book here again no questions asked.

What a great stay. The location was fantastic, and a very easy walk to the Shakespeare festival, and tons of great restaurants. Safeway is also only two blocks away. The place was immaculate. The bed was super comfy and the kitchen well outfitted. I recommend it!