Family-friendly vacation rentals in Ashland

It was such a beautiful and cozy little quaint place, easy to walk to restaurants. It was so calming and welcoming. We will definitely book again love the hosts. They were so kind I could not have asked for a better little getaway.

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.

We absolutely loved our stay the first time, so wanted to come back for our honeymoon! Jonathan and his family were so welcoming into their beautiful home, we will absolutely be returning!

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.

Ed and Jacquie’s place was exactly what we needed. We were on a road trip moving some stuff and towing a trailer, so finding a private, safe spot where we didn’t have to unload everything was a big deal. Their property was perfect, and the pull-through driveway made it super easy to get in and out with the trailer. On top of that, Ed and Jacquie were incredibly kind and welcoming. Honestly, some of the nicest hosts we’ve ever had. The property was peaceful and relaxing, with a creek out back, and the house itself was cozy and comfortable. We felt right at home. I only wish we could have stayed longer! If you’re in the area and need somewhere to stay, definitely stay here. We’d come back in a heartbeat.

Amazing, spent Valentines day there. The hot tub is great, nice view to the forest, everything calm, not noise and super clean.

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.

The home is very open with a large living room for family gatherings. We opted to pay the extra $200 for the pool to be heated and have no regrets. The kids swam morning to night while the adults enjoyed the hot tub. Kirk was great at responding to our needs. The home was clean and plenty of towels were provided. Kitchen had all the essentials which was much appreciated. Highly recommend.

This was a lovely place to stay. The hosu was clean and spacious, with nice views of the valley, and in a quiet neighborhood. Walking to downtown or the dog park was easy. I would definitely stay here again.

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.

Thank you Teresa. Enjoyed your quaint cabin space and the grounds/river. Hope to see you again when we slide through this area.

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!

I'm a repeat to King of Queens. Suzanne's place is perfect for my extended stays for work. My dog loves the fenced back yard. Suzanne is an amazing host! I always hope her place is available when I need to go to Medford! Highly recommend!

This space is comfy and peaceful. Easy walk to OSF. The towels and sheets are primo! Highly recommend.

Excellent space, extremely comfortable and easy to operate the system inside! Felt very relaxed and “home vibe” 10/10 mattress and very comfortable recliners great to watch a movie in! Everything you need at a great price and very responsive and helpful hosts! Thank ya’ll so much!

Wonderful place to stay for a short vacation. Close to everything with beautiful views of the valley. The airstream was cozy and warmed up nicely in the cold weather. Had most everything we needed and was clean. The bed was comfortable. Would recommend, especially if you are accustomed to staying in tiny spaces.

We have stayed here several times for many reasons mostly what great hosts they are but really love their place comfortable peaceful and still close to everything Love the little extras they do to make us more at home

We have stayed at Claudia’s several times and enjoy her hospitality and the peaceful setting outside of Jacksonville. A great spot for a couples Getaway!

Highly recommend this stay. Walkable to downtown, very clean, well stocked, excellent water pressure and HVAC. Even though it's an old historic house, it has been updated well and doesn't feel old and drafty.

What a magical place to stay. Clean, picturesque, peaceful. So happy we stayed here. Lovely hosts 🌸

I had a lovely 2-week stay here while I was in bike mechanic school. This cottage is located in a lovely, historic neighborhood and there is a bath and tea garden right next door. You can walk (or ride a bike) to just about anywhere in downtown Ashland. The cottage was clean, had a good climate control system, firm mattress, cable television and amenities. The kitchenette is small but adequate for me and the bathroom is really spacious and new. I highly recommend this one!

Great place to explore Ashland. Loved the deer in the yard. It’s a bit dark to walk home at night but the area feels safe.

Great location, easy to get everywhere we wanted to go. Quick responses to questions we had

The studio is a cozy snuggery! Some highlights: super comfortable bed, fun art in bathroom, cute flannel sheets with woodland creature print. But the best part was GG herself. Even before I got to town, she was able to give me insider information….the restaurant I wanted to visit would be closed on that day. Then, the night I arrived I took several wrong turns on my way to the property and needed a LOT of help from her to find my way. GG even stood outside the house on that bitterly cold night to guide me in. So kind and helpful! A wonderful experience!