Vacation rentals with outdoor seating in Jackson County

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.

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.

Cherry and team did a great job keeping us informed of how to check in and other amenities which were present. The place was relaxing and peaceful for our guests. It was fun seeing some boaters pass by the place every once in a while.

Absolutely beautiful home with great owners!! Super quick responses and clear on everything. The master bath was by far my favorite part of the house along with the beautiful kitchen. Super great stay and would 110% recommend! - is on the main road so be careful when pulling out

A great experience from start to finish. The house was clean and well appointed. The 5 king beds were all clean and comfortable. Great televisions and a nice backyard. Small details were the key to a great home. A wonderful set of knives in the kitchen and all the spices you could want. You’ll love this house!

The house was very clean and met all of our needs. We would definitely stay there again.

This is a great family home, lots of games to keeps kids entertained, beautiful art decorations around the house. Our kids loved it there they didn't want to leave! Very well thought out vacation rental, has everything you might need. The views are amazing, we loved our stay and will definitely stay here again. Great host with flexible check in time. Thanks again Jessica !

This house was one of the best stocked rental homes I have rented. The mattresses and linens were comfy. The house was peaceful and perfect for a retreat weekend with friends.

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

Well worth the 14 minute drive out of town. The ranch is gorgeous with thoughtful features throughout (fire pit, roping practice, rope swing, seating areas with the best views in mind). We spent the majority of our trip just enjoying the house and space as the entire ranch feels like a vacation! Quiet. Hut tub was clean and warm. The pool was lovely, we would consider coming back in the summer just to enjoy the pool!

Great location and excellent owners! Highly recommend to all!

This is our go-to place to stay while visiting the area! Once again, a wonderful experience with lots of thoughtful touches. Highly recommended!

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.

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.

Patsene, the host is lovely. I came to visit my old neighbors, and they found her as pleasant, as I do. Apt is a well appointed separate location, on her large property..tucked on a quiet street, but close to great stores and food. Patsene is knowledgeable and exudes an interest and amiable attirude, to aide you in achieving your goals. So pleasant..so generous (!) Fresh fruit, and other snacks were left, with filtered water..a nice reward for one's weary travels. Many extras are present, that other Airbnb's Ive enjoyed, had overlooked. Patsene happily offered me a blender for shakes, plenty of luscious towels ( I noted the brand, and of her rug. Buying both!) I intend on always staying there now, once a year..spent 4 nites, and wished I had more. All advertised, is better than you imagine, and she lends class and comfort, in a private location. Thanks Patsene..you're one of my faves (!) Been to many Airbnb's, but none with your kindness and charm!Dont forget me..I'll be back! Cheers!

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.

This condo is in a great location. Short walking distance to the theaters, restaurants, grocery store, etc. It was very clean and tidy. On the other hand, I found it to be completely without any character. It looks like one big hotel room, decorated by house stagers with limited imagination (think lots of fake plants, bowls full of wooden balls, etc.) But as a place to sleep and have breakfast, it was perfectly nice. Excellent communication with the host.

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.