Family-friendly vacation rentals in Ashland

I cannot say enough about this listing. We were wishing we could just move in and not go home! Elizabeth and Mark were very gracious, helpful hosts. The listing is cozy and immaculate. The outdoor space is incredible. Ashland is wonderful, as well. We would be willing to move to Oregon, in general, if all our family wasn't here. Thank you Mark and Elizabeth! We hope to return again and visit!

This was a gorgeous and cozy retreat. The space was very clean and comfortable and the hot plate worked well for cooking simple things. Well stocked little kitchen and I really appreciated the air conditioning since there was a heat wave during my stay. Most of all I loved the private feel of the space and the picture windows overlooking beautiful madrone trees. And it was just minutes from the East Applegate Ridge Trail, with dramatic and iconic views at every turn. I would love to stay again.

We loved our stay here. Great location... walkable to restaurants, coffee shops and grocery store in Talent, and easy drive to Ashland, Phoenix, Medford and Jacksonville. House is cute, cozy, private, clean, and has everything you need for making meals at home. Beds and bedding were very comfortable. Highly recommend!

We have been staying here for years, and this is THE perfect spot for a getaway weekend to watch plays. A short walk to the shows, breakfast down the hill, high tea a block away. The room is spotless and the full kitchen is a blessing.

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

I had such a lovely stay. Finding it and getting in was a breeze. The house was peaceful and comfortable and had everything needed for a 5 day stay. The bed was very comfortable as well, slept like a log. Communicating with Cynthia was easy with fast responses to questions. It took me a bit to figure out the internet, Cynthia answered right away and told me what I needed to do. The only thing I regret is not taking a nice hot bath in the deep tub, and I didn't use the epsom salts I bought for a soak. Just didnt get around to it which was a bummer since my tub at home is too shallow to enjoy. If I come back to the area again I will definately check to see if this amazing place is available first.

Raleigh was a great communicator and made the effort to welcome us and introduce himself. We had a mishap where we locked ourselves out and he went above and beyond to help us get back in. Lovely home in a perfect Ashland location!

This was the perfect location for my California & Oregon family to celebrate Christmas. There were toys for the toddlers and even a small Christmas tree. The bedrooms were cozy and warm. And Kitchen was well supplied. 30 minute drive to the snow recreation area. Their dog Austie was a family favorite. Thanks for making our Christmas merry!

Kirk and I communicated a number of times for clarifications as needed. We hosted a large family Thanksgiving dinner and wanted to make sure we had all that we needed. It was spectacular. We had our two young grandkids and the box of kids toys and outdoor toys was wonderful. The gazebo with Fireplace and the gas firepit on the deck were wonderful places to gather during the late Fall coolness. The home was spectacular for our 8 adults, 2 kids and 1 dog. . . Could not have asked for a better stay.

Very beautiful area. Had lots of fun in the awesome pool. My daughter was amazed at all the wildlife in the area. The room was very charming and had a rustic feel to it, but had all the modern amenities. All in all we had a great time and couldn't ask for a better location or host. Teresa was very friendly and helpful

My husband and I were in Ashland for the Shakespeare Festival, and enjoyed a fantastic stay at Katy and Jesse’s cottage-above-the-garage. They were delightful hosts who were quick to answer questions, but gave us plenty of space to make ourselves at home. The location was perfect— super quiet and a quick walk to theaters and restaurants. Everything was clean; the air conditioners were nearly silent, and the uncluttered, well-equipped space worked beautifully for us. Highly recommended! We look forward to returning!

Kirk was responsive and accommodating to our needs this weekend. Helped make for a great retreat.

When the Oregon Cheese Fest was postponed, we decided to keep our reservation at Melissa's place and have a cheese fest of our own--we are so glad we did! Melissa's place is so cozy and stylish, and is absolutely perfect for groups. The hot tub was a wonderful touch as well. Melissa was so communicative about how to get into the driveway, and encouraged us to ask for anything we may need. We had a fantastic time, and would definitely stay again. Thank you for everything, Melissa!

This was my second visit to the Barn. I came back this time with my family because I wanted them to experience this special place. The Barn is an amazing space since it gives the peace and tranquillity of a rural setting in a well designed great room area downstairs and 2 large but cozy and comfy bedrooms upstairs. The outside patio was a great space to read, draw and share wine with my family. All of this and only 10 minutes from downtown Ashland. Additionally if you are a hiker there is a trailhead a very short drive away. Communication with Jenn was great throughout our time there. We had the bad luck of being in Ashland during a rare power outage that impacted power in parts of Ashland and Medford. Jenn was great in responding to my questions when the power went out and following up to get information from the power company for us. We also had an problem late at night with the water but Jenn responded to my question and immediately tried to fix things for us. Even though the problem couldn't be fixed until the next day Jenn did everything in her power to make our stay comfortable. I was very impressed and would strongly recommend her as a hostess and this home to anyone to who loves a rural setting.

We liked staying at the house in which actually the family was living. We felt as if we were welcomed as their family guest. The culture was akin to mine. The artisan wood floor and ceiling made a huge difference on our spirit. Very beautiful house!

Oh my gosh, what a wonderful little perfect cottage in the perfect area. We loved how cozy this cottage is. Just the perfect size for two of us. Our hosts Jackie and Ed were wonderful, responded in a reasonable time frame, if we needed anything. Jackie even provided a crock pot for us after asking if one was there. Very glad to have found this place. I believe we will be back if it’s available the next time we are in Grants Pass. It was very close to our family as well. Bonus points there!! Thank you Ed and Jackie, we will see you again. Liz and Richard G

We were in the area for a soccer tournament and this house was perfect. We were close to the fields, easy to find, comfortable environment, and quiet neighborhood. The hot tub was meticulously clean and perfect to end a long day. We enjoyed late at a recommended restaurant and it was excellent. Would definitely stay again.

I absolutely loved this private retreat in Rogue River, the space is so clean and sophisticated and ties in so well the natural elements that make it so calming. I regret that I could not stay longer, but if I’m in the area again I would love to stay again. The hot tub was a great late night moment of relaxation for myself, so glad they have that! I felt like I was staying with friends. Thanks Lyn & Jim!