Vacation rentals with outdoor seating in Ashland

This is such a beautiful home. The setting in the winery is an added bonus. Peaceful, relaxing and refreshing. We rented the entire house and it worked out well. There is the common room but also we had our separate bedrooms to retreat to whenever we wanted. The host was extremely helpful, kind, and responsive. The staff at the winery were extremely friendly as well. The pool and hot tub were clean and easy to use. There wasn’t one bad thing about this place. It is set up perfectly for a family to enjoy a nice home. Even without renting the entire house you still feel like you’re the only one there. Such an enjoyable experience. Will definitely stay here time and time again. Thank you to Valisatie for being such a wonderful host. The house and property are beautiful.

Amanda's place is great! The attention to details for necessity is amazing. Every room is well stocked and you will have everything you need even down to the feminine products and disposable razors. Our two pups had a great time too. The backyard is perfect them to roam around. Amanda even had a jar of dog treats by the door. The beds were big and conformable. She is also very responsive and flexible on the check out time. Overall, top notch quality!

This is a comfortable home. You can also walk for miles on roads or up on Roxy Ann Peak . I felt very safe here. A great neighborhood.

Darline’s house is beautiful! We came for fishing but our fishing trip was canceled so we just ended up hanging out around Grants Pass and at this wonderful house. It is well stocked and Darline has thought of everything. There’s extra towels, even sanitized swim wear incase you forgot some for the hot tub or the pool! We were so pleased with our stay!

The house was so clean and beautiful! one of the best Airbnb experiences I've ever had. Stefanie responded quickly whenever I needed anything and the house was so cozy and spotless clean! would 10/10 recommend staying here!

Easy walking distance to Shakespeare festival theaters and to Oregon Cabaret Theater. Also to lovely downtown shopping and eateries. Cute comfortable place. Feels very safe. We would stay here again.

Loved the place! This is our second stay! Such a great and cozy home especially for a family. Kitchen is wonderful, great for those with food allergies. Very well stocked! Bed is super comfortable! We will definitely be returning! Great communication with the host!

We had an event in Grants Pass and our family enjoyed staying a week at Jennifer's place. Everything was as it is described in the listing. Check in and out was easy. It is quiet and peaceful. We felt like we had enough room for everyone and slept well! Jennifer was quick to respond to any questions we had and provided us with clear instructions. Next event we have we will book again.

We had a great stay. The apartment was comfortable and provided everything we needed to feel at home. The forested surroundings were beautiful and peaceful. The hosts were friendly and helpful. They thoughtfully provided a small table, high chair and toys for my children which we greatly appreciated. Highly recommended. Thank you!!

This is easily the best experience I’ve had using this app. This host is responsive, and the accommodations are exactly what you’re hoping for. Specifically if you’re visiting for OSF, this location is the bomb because it’s not down downtown so it feels quaint not crowded and the restaurants nearest don’t fill up as fast as they do closer to theaters. Having a Safeway across the street is a dream.

It was just what we needed and the bed is the most comfortable I’ve been on

We stayed at Kirk’s place for Christmas and it was just perfect! The studio was clean and welcoming when we arrived. Fireplace was on for us and we were able to enjoy the amazing hot tub that night. We had a simple dinner and the kitchen had everything we needed. The two beds were beautiful and so comfy! Not your typical hotel style beds but instead soft and luxurious with thick comfy comforter. Shower had a dispenser for shampoo, conditioner and body wash. The location is also very quiet and the river access was just lovely. Very kind hosts and super accommodating. Would stay here again in a heartbeat.

This was our second spring staying at Leslie's beautiful rental. You can't beat the location. We parked on Friday and didn't drive again til we headed home. We explored Ashland by foot with great food, live music, visual art and plays just steps away. We will 100% be returning!

Jennifer has gone above and beyond to make Suite Madrona a very comfortable place to stay. I was there for a full week and could not have asked for more. She has attended to every detail. In addition, she recommended some wineries in the area I did not know about. This lovely enclave is only 15 minutes from Ashland without charging Ashland prices, and very close to the airport. I highly recommend Suite Madrona.

Great spot to stay as a quick stop over on our way to San Francisco! Would stay here again!

What a wonderful stay! Cowslips Belle did not disappoint. We stayed for 10 days, and can honestly say that this was one of our best AirBnB stays ever! It’s walking distance from the hub of Ashland - Main Street, lots of restaurants, & Lithia Park. It’s a beautifully maintained peaceful retreat — all 6 units face a private, lovely grassy area (that our dog thoroughly enjoyed), with a Koi pond too. Our unit —the Lower Unit—was clean, quiet, and had everything we needed. The hosts are friendly, personable and communicative. Even when there was a temporary water shut-off issue, they let us know every step of the way what was happening, and it was fixed within an hour. If you’re looking for a restful nights sleep, on a comfortable bed, with a jacuzzi bathtub & separate stand-up shower, with a full kitchen, then look no further! We are definitely planning on staying here again.

We visit Ashland regularly to visit family. I’ve traveled a lot, and this was one of those rare good finds. The host is wonderful, and so is the place. I loved the modern, minimalist, yet natural and warm interior and it’s very convenient (the Co-Op, etc). It was very quiet, too. We’d stay here again in a heartbeat.

The perfect place to stay for the Shakespeare festival. Valisatie was so helpful, even when we needed to move our reservation by a day. Walking distance to everything in town — dinner, shows, shops, Lithia Park — we were truly able to park the car and leave it there until we headed out. Thank you so much!

This is my second stay at the condo. I love the location as everything is walkable from this spot. Didn't need my car at all during my 4 day stay. The space gets great light and there are nice views of the surrounding hills. Everything worked great and the entire condo was spotless. If one were planning on doing a lot of cooking, you would need to bring provisions as only salt/pepper and oil are provided. Not a concern for me as there are so many restaurants nearby, and the Ashland Co-op is just down the street. Nice to be so close to everything and yet also in a nice, quiet location. I will be back.

The condo penthouse was amazing in every way. Beautiful, spacious, clean, and in a great location.