Family-friendly holiday rentals in Ashland

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!

Private, peaceful, and in serene settings along the Applegate River. Place looked exactly like the photos and had everything you need. The river was better than expected, everything you could want and more. Lastly, the hosts were very welcoming and put a lot of thought into make this a great place to stay!

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!

Great location for the theatre festival, just a 10-15 minute walk to the theatre. Very quiet location, off the main road. Spacious, clean quarters, well-provisioned for visitors. Mini market five minutes away by foot for last minute drinks/snacks. Host is super responsive and helpful and provided a winning restaurant recommendation.

We had a wonderful stay at this Airbnb. It is a cozy and inviting space! The beds were comfortable, and everything was very clean. The hosts have considered nearly every detail you might need in the kitchen, bathroom, and bedrooms. They provide a link with useful information, which was helpful. We truly felt at home. The sound of the river at night was priceless. The place offered great privacy, allowing for a genuinely relaxing experience. Thank you for making everything a breeze.

Wonderful place to stay. I had a problem on my end with reserving the wrong dates and Michelle was great to work with, and was immediately responsive, to fix the error. We stayed on the property with 11 college students and everyone had a great time and it served as a comfortable and safe home base during our visit to the Oregon Shakespeare Festival.

Candace and RG's place is a real gem. We stayed for an entire month and enjoyed every day of it. The house is fully equipped for extended stays. If you are an outdoorsy type you will fall in love with their gorgeous property which has an extensive network of trails to hike. Candace and RG are wonderful folks and since we are now moving to the area we already have new friends. If you want to spend time in the Rogue Valley but stay out of the urban sprawl you'll be hard pressed to find a better spot. Five big stars!

Loni and her husband were easy to work with, communicative, and very kind! We used to live in Jacksonville and were excited to find an AirBNB right by downtown to walk around during our visit back. The historic home (c 1865) is private, air conditioned, with a beautiful little kitchenette. Equipped with children’s toys for our infant and Loni provided a Baby Bjorn bed and gate to keep him off the stairs! He’s awfully mobile though and we had to watch him around end tables and lamps, just to alert anyone traveling with a crawler/cruiser. The mattresses could probably use an update, but in general we slept well anyway. Would stay again!

The property was beautiful and the home was quaintly decorated and had a cozy cabin feel. The beds were very comfortable and the kitchen was spacious. The whole family enjoyed the zip line and priceless memories were made! I would absolutely stay there again. We didn't want to leave. Access to the cabin was about 2 miles down a dirt road that allowed us to frequently see deer relaxing nearby. Spectacular!!

We found Joe’s place to be very charming; the furnishings and the sun-lit living room and the kitchen; beautiful, artsy, clean and cozy. The bedrooms were also great with very comfortable beds! Joe was a super host; very communicative and responsive. The house is located on a busy street, so there is some traffic noise, and it isn’t a place that you can talk walks from.

Really wonderful studio! I loved having a well stocked full kitchen. Studio was very clean, easy to find, private and quiet. Views are nice and it was such a relaxing space. Tina is a great host. She is friendly and responded promptly to every question I had. Neighborhood is lovely, and there’s a beautiful park about 3 blocks away. Overall such a great stay.

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!

This is an amazingly magical location!!! We had an incredible time exploring the property - it was really fun to hike around, there are incredible views and even a waterfall. There's a very friendly donkey who was so sweet. Our 2 year old was in heaven! Loves the sweet fire pit area to sit aroundm This place was just the best! Highly recommend and we will be back!

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

This place is a gem! It’s the best Airbnb we’ve been to. The property is gorgeous - such a wonderful place to relax with a spa and multiple areas to enjoy the outside along with an incredible view of the Rogue River. We spent hours on the dock - reading, eating, & sunbathing. We loved watching the geese and ducks with their babies on the water. The studio is super cute and had everything we needed including the most comfortable bed. The location is perfect. It is such a peaceful, quiet spot yet we were 5 minutes from the cutest town with amazing restaurants and shops. Kirk is so friendly - a wonderful and gracious host! We would love to go back!

This is a great place I have stayed there every time I come to town. big enough for large family event. close to stores and downtown