Kid-friendly holiday rentals in Winchester

Emily and Randy's lake house is upscale, peaceful and in a great location. Access to the lake and pool are literally right outside your door and the town square, which has several nice restaurants, is a mile down the road. We enjoyed our stay and would definitely stay there again.

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.

Amy was very helpful and accommodating. She was helpful and answered all my questions. I will be reserving it again for sure

Mulberry cottage was beautiful. I love antiques so the furnishings brought the home to life. It was the perfect place to come home to so we could relax after a busy day with the grand kids. The front yard landscaping was beautiful with all the white hydrangea blooming. By being located in town, we had everything we needed close by. Thank you Judy for a wonderful time and we hope to see you again soon.

I’ve probably stayed at over 100 Airbnb’s over the years and this one is definitely in the top three overall. Fully stocked, spotless, convenient, responsive host, and just a wonderful property. Right across the street from the community pool and the lake. Literally couldn’t ask for a better place for a relaxing weekend with families.

If it wasn’t for your great directions we would not have found it because there was no address posted at end of driveway We want to thank you for allowing us to stay at this beautiful house. It’s a piece of heaven on earth. We will definitely be back!

Great location, on the water with dock and only 5 min walk to a grocery store or 10 minutes to square with restaurants, movie theatre, etc. Would stay again!

This is one of the best places I’ve ever stayed. I’m usually the one who wants to go back home early even on 30A, but this was so peaceful and relaxing that I could see myself staying forever. The Tims Ford lake + kayaking was so much fun. They have all you need- vests, paddles etc. And a trailer to hook up if needed. We have a truck so that wasn’t necessary but there’s also the awesome Polaris ranger you can ride around on. We are a family of 4 plus dog and it was perfect for us. Felt comfortable walking around also. I felt so connected to God while here- it was an absolute recharge. Noni was A++ communicative and proactive so there weren’t any questions on our end. The ONLY and I mean only thing that was a little pain, was- the front door is a little wonky so you have to be extra careful to shut it (with kids you have to double check)- but again- Noni communicated this beforehand. I can’t wait to book here again!

Great view of lookout mountain from rooftop! Very clean and comfy place. Would definitely recommend! Great stay!

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.

Wonderful! I had an amazing stay. The bed was one of the most comfortable beds I have ever slept on! The decor was so fun and yet so homey! I loved the area as well!The mountains are so beautiful!! The hosts were responsive, friendly and kind! Neighbor Sam was the coolest! This is an amazing value! I will absolutely return! 😊🙌

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.

We enjoyed our stay at Brad’s place. Very clean, very spacious and close to downtown! Would definitely book again in the future

This place was so cool! It was a quick overnight stop for us on our way back to Ohio from Florida. Although it is off the beaten bath from the Interstate, it was so worth it!! My husband and I and our 2 adult sons thought the place was amazing! So much so that my oldest son wants to bring his soon to be wife there and stay at all of Kristi’s magical places! I’ve never seen my boys and husband so excited about a place! I only wish we had had more time there to explore all the neat treasures inside. Maybe next time…. This place is definitely one we’ll remember!

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.

Beautiful place to stay, very quiet and peaceful, everything was as described, loved that it had everything we needed, the games and toys were a hit with my granddaughter, I love that it was so clean, and there is lots do within walking distance, will definitely stay here again!!

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 🥰

Our stay was great. The apartment was exactly as presented and had what we needed. It's very walkable to the downtown area to skip the traffic. The bed was comfortable, and the sound machine was a nice touch. The restaurant across the street became our spot for a good-priced meal. The pool area was great, quiet, and clean. Our only issue was totally due to user error on my part, initially getting into the building, but Jessica was immediately available to help. We had a great stay.

Great and comfortable place to stay. Check in was easy. Very close to everything, restaurants, museums, ruby falls, rock city, etc. Noise was not really noticeable from Main Street. Had most amenities. Paper towel was half of one and only two laundry pod were provided. We traveled with a two year old. They provided a pack and play and high chair which was great. Host was very responsive, attentive, and friendly. Overall, I would stay here again. Good experience.

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