Kid-friendly holiday rentals in Winchester

Lovely home, perfect for me and my toddler. He especially loved the bunk bed room. Plenty of towels, good coffee marker and nice bedding. Communication with the owner was pleasant and clear. I’d recommend and would stay at this home again.

Enjoyed time with friends and our little ones over new years. This was a great spot. Especially loved how many rooms had their own restroom and the upstairs area.

This place was exactly as listed and was very comfortable and cozy! The location was great and we had a great time staying here with my family 😊

Beautiful place looks like brand new construction, great location, everything was done with excellence!

This was the second time I stayed here. It was close to my work. Also very nice and peaceful location. If I come back that way this is where I’ll stay.

This was a great place. The boat ramp was super close and the covered boat dock was great. The house was clean with plenty of room for my mom's 70 birthday celebration and Memorial Day (the 9pm neighborhood curfew would have been nice to know prior to booking but we made it work). The description and pictures were exact as shown and described. We are definitely gonna to book again in the near future. Great job Derek!!!

My wife and I stayed here for our honeymoon and it was absolutely perfect. The location is great as it is close to hiking areas, restaurants, and Chattanooga without being too busy! The house itself was beautiful inside and out. It was clean and tidy, the beds were comfortable, and it was stocked with anything we could have needed. The hot tub was extremely nice and clean. It was very spacious. The sound of the interstate was not bad once you got inside and if you are a light sleeper, David provided ear plugs and white noise machines to cover the sound of the interstate. However, the interstate sounds should not deter you from this stay because the house, host, and location are all excellent and outweigh the noise. 100% recommend and will be staying here again.

Lookout Mountain Birdhouse is a new property, so everything is shiny and clean. While just off the road, it's very private. It's ~30 minutes to Chattanooga proper, but that worked OK for us. Lacy is a true gem of a host and great to work with. She promptly answered any questions we had and stayed in touch. The good and the bad: the tall, west-facing windows make for a bright house and a beautiful view, but the windows in the living area have no shades, which can render that area almost unusable in the late afternoon on a clear day. That said, we would definitely stay there again. We particularly enjoyed the Sunset Rock via Craven's House Trail, and the Montague Sculpture Garden in Chattanooga. The tour of Chattanooga Whiskey Experimental Distillery was fun, too.

Michael’s house on Lookout Mt was excellent and right across from Rock City. The place was easy to find, well equipped, and clean and ideally located for both Rock City and Chattanooga.

Adam was very responsive and provided clear instructions. Eveything was easier due to his guidance. Some of the outlets didn't work, but the ones that did were enough for the electronics I had. While parking wasn't free at the location, there were plenty of free parking spots on the streets around the building, so that wasn't an issue. Overall, 5/5 it was a quiet, clean place. What makes this 5 stars is for me is Adam himself.

The property was as described, hosts were very communicative and the on site caretakers were very kind. Was very cool to watch the hangliders so close to the property

Great place to stay for the wedding we attended at Twin Creeks. Close to everything. Walnut Hill is great for coffee every morning. We would stay here again.

A very peaceful place to stay! Very close to things I enjoy doing - hiking, learning about the area. The guest house was very clean and I felt at home with the comfortable furniture and bed. The four-leggeds, Ginger and Belle, came to visit every day which was treat for me. I highly recommend this guest house and Tammy and Jo as hosts.

Excellent! Beautiful, quiet stay at the base of Lookout Mountain in historic St. Elmo. Walkable to local food, the Incline, and just 15 minutes from sweeping vistas at Point Park and other iconic Chattanooga overlooks. Clean, well-kept, and private with dedicated parking. Note: Greg will meet you on arrival and provide some orientation to the area and the airbnb. If you have heat sensitivities, be aware that the AC may have a cooling limit set.

loved how accommodating the team was. got a welcome phone call right before I arrived which made me feel appreciated. the place was amazing. my group is already talking about planning the next trip here

Really cute unit, can't beat the price

Peaceful, clean getaway that feels like a home away from home. I highly recommend!

Gary's place was excellent! It was just what we needed after wedding activities at Gardens of the Gorge. This place is very quiet at night and a great place to unwind. The view from the balcony is so nice and was a welcomed sight each morning. Thank you again!

Sarah and Brandon's place was great for our family of four. There was plenty of space for us. It is in a convenient location to get to the aquarium and restaurants, and was easy to navigate to from the interstate. Our kids enjoyed the pool and appreciated the provided pool towels. It was just right for our visit to Chattanooga, we'll book again when we're back.

This doll of a host was so gracious and gave us immediate access when we arrived at an odd time. Their home is gorgeous with just the loveliest surroundings. Make sure to take a few minutes to watch her bird feeder! Cardinals, bluebirds and finches 🥰

What a wonderful location right next to all the things we wanted to do and see. We walked most days to our destinations and others were just a short drive. I’m so thankful for the noise machine in the room to help us sleep since we were right in town. The access to the condo used impressive technology and it worked every time I used it. There is a bicycle rental station at the park right down the street. The aquarium and other fun downtown spots are a quick walk away. Ruby falls is a quick drive. We had so many wonderful experiences from this location. The condo had everything we needed inside.

Very nice new apartment, extremely clean, comfortable king bed, walking distance to parks and restaurants. We loved our stay at this condo.

Awesome!

This was a great stay! As advertised, and with lots of resources to explore the area. We were only staying one night as part of a roadtrip, so we didn't get to experience the area, but the place was very comfortable.