Kid-friendly vacation rentals in Winchester

It is a very quaint older home but well cared for. It is on a road that is somewhat busy though, considering we were in the country. We were surprised by how many cars drive by. However, Annette is very kind and helpful the house was a good value.

We had a great stay at Gary’s place and enjoyed all of the amenities and nearby hiking.

Jeff was a great host! The house was very nice and comfortable. Would definitely stay here again.

This quaint little house is Estill Springs is perfect for a family or a few couples to get together and not be too in town but also close enough to anything you might need. Plenty of space and things to do from movies to games and the screened in porch out back is very nice to relax and listen to the sounds of nature! It’s close to family and we will likely be back in the future!

Great place and great host would definitely want to stay again. This is an ideal place to stay if you are seeing a show at the Caverns.

We had an amazing stay at this Airbnb! The breathtaking views made every morning feel like a dream, and the hiking trails nearby were perfect for exploring the natural beauty of the area. After a day of adventure, it was great to have fantastic dining options just a short distance away—plenty of delicious choices to enjoy. The host was welcoming and the accommodations were clean and comfortable, making the entire experience even more enjoyable. If you're looking for a relaxing getaway with stunning scenery, outdoor adventures, and great food, this place is a must-visit!

Great older home with quaint charm. Very clean and conveniently located. I would definitely stay here again. Host was responsive and asked if I needed anything as soon as I checked in.

Nice quiet area but only minutes from restaurants and shopping. We had a nice relaxing stay and recommend the Kitty George house if you love peace and quiet.

Jodie was extremely helpful in accommodating a guest we were hosting on campus who needed alternative accommodation at short notice. We're very grateful for her responsiveness and flexibility!

My family and I were beyond impressed with this rental. We had dinner at Filo's Tavern as soon as we arrived. The environment was lively and the service was very hospitable. I highly recommend the Mongolian Ribeye Steak if you like a sauce that is on the sweeter side and we also had the special for the day which was Swordfish Kabobs on a bed of rice. The Swordfish was plated beautifully and tasted fantastic. The interior design was extremely charming and well-designed. I could not stop gushing over the wallpaper, floors, ceilings, light fixtures, door knobs, shower/bathroom sink fixtures, photos, bathroom mirrors, stairway with lighting, exposed brick and little house plants that were scattered throughout the space. Everyday I was able to prop my laptop up on the deep window seals that face the square and work while watching everyone move about town. We loved watching the march madness games every night on the gigantic t.v. while having foosball, board game and arcade game tournaments.

This was our second time to stay here. It was great definitely would stay here again.

Our stay at the loft was perfect for our visit. We enjoyed the amount of space with ample seating and living space. Joy was responsive and helpful during our stay. We look forward to staying here again.

This was our third stay, and it has been satisfying to see the investments made in the property over time. First there was the addition of outdoor amenities like a picnic table, grill, and lights. This time we noticed upgrades like a new mattress, TV, and coffee table. The hosts were super responsive, too, when something came up. We look forward to seeing what’s next!

10/10 stars for this spot! Very private and cozy! Would absolutely stay again! Dom and Bonnie both incredible neighbor doggies! Full kitchen. There is nothing bad to say about this space!

Robert was fantastic. He checked on us to make sure we got into the property and had everything we needed. Such a friendly guy! The bed was really comfortable and the unit was clean. The property has camping spots, cabins and the studio we stayed in. I was worried it would be loud staying above the bathhouse for the cabins / campers but it wasn’t. We had such a great time at the Caverns for the concert and then enjoyed a firepit and hanging out with others staying on the property. Easy walk to the concert venue. Definitely will stay again. First class host!

We had everything we needed for our one night getaway. The place was gorgeous and exactly as it said. Would definitely come back again to stay!