Kid-friendly holiday rentals in Winchester

We enjoyed our stay so much! The house was absolutely amazing and met all of our needs. We loved the attention to details and all the little things that made us feel at home. The hair elastics in the bathroom were greatly appreciated with 2 young girls. We all were comfortable in the well laid out home. Had a blast in the secret game room and made a lifetime of memories. 100% recommend this property and will definitely rent from Desmond and India again. Thanks!

Jenny was a great host! She was very communicative and responded to us quickly. It was really good to have such a fully stocked kitchen. We loved not searching for everything. Everything was very clean, tastefully decorated and not cluttered. The location was very close to all the good restaurants and attractions.

Great location on Chattanooga's North Shore. Very clean. Nice beds. Easy walk to grocery store, dining, etc. Just across the river from downtown Chattanooga. You need to be able to manage steps as there are a few getting in and out. Owner was very responsive and anxious to help us have a good stay.

Location! location! Jeff’s place felt just like our cottage on the lake in Ontario. Quaint, clean, fully stocked and came with sweet extras like a bottle of wine for us and a dog bone for our fur baby. You cannot beat the location ! We wish we had more time to spend in the area! A great bonus is the yard space for our dog and we sat like a couple of old fogies and had our wine on the front porch during a thunderstorm. Jeff was extremely responsive and accommodating. Thank you for sharing this gem with us!

We had full capacity of family. Marci was so accommodating and responded quickly to any questions we had. She was concerned that we were comfortable and had everything we needed. She was the best host!!! We enjoyed our stay and the kids had a ball with the yard, roasting marshmallows!

This was a beautiful, peaceful home. It had a large, open yard for my dogs to run with plenty of indoor space as well! We will definitely be coming back on future trips.

This is the second time my family and I have stayed at Lynn's place. It was exactly the same accomodations and the house was the same as they were the first time we stayed which was immaculate, quiet, we felt just like we were at home away from home. The only downfall was coming home after such a fantastic spring break vacation. Thank You Lynn for being such a gracious host.

Beautifully designed home, comfy, clean, and in a great location. It was so nice to relax on the front porch after a long day of travel!

Gorgeous space with lovely little details throughout. The location is a perfect homebase for exploring Southside and Downtown. After a day out and about, we found ourselves just as excited to get back and enjoy the apartment with it’s rooftop mountain views, twinkly spa shower, and the most comfortable beds. We also enjoyed learning the history of the building. The size was perfect for three adults but has plenty of room for a family or couples traveling together. We’d love to return to this cozy, clean, and stylish spot!

Nice place , loved the floors, patio, private. Great communication w host.

Had an absolute great time at this cute Airbnb. Very relaxing and loved watching the hang gliders! And great location.

Our stay was wonderful. The house was very clean and comfy. We loved seeing the rabbits in the yard in the morning and afternoons. Ginger (the dog) and her friend the kitty was super sweet and friendly and the best greeters you could have lol. It was a very private and quiet stay even though the owners are located on the same property. The property is very pretty with the wildflowers and gardens. We would definitely stay here in the future.

It was very nice well-appointed, with everything we needed. Enjoyed the location. It couldn't have been much closer to the incline railroad. It was convenient to Lookout Mountain and the battlefields, and the local restaurants in walking distance were great

We stayed here for the 2025 Easter weekend. The description of the place in AIRbnb is accurate. There was parking for two cars. The area was safe and you are two blocks from the free trolley to get downtown. I would easily stay here again if needed.

Our family of four had a great stay at Brad's place. It was a great base for exploring Chattanooga and close to so much. We loved being able to walk right into the neighboring park for hiking. The beds were comfortable and there was plenty of room for all four of us without feeling crowded.

Perfect place for my and my daughter to stay. Bonnie was very sweet and helpful. Peaceful property!

This condo is very clean and the photos in the listing match exactly. It is very easy to find and located close to restaurants, bars, and all the attractions Chattanooga has to offer. In fact the Parkway Pourhouse restaurant is located directly across the street from this condo and has great food. The host Shaun was very helpful and accommodating. He checked to make sure my wife and I had everything we needed to have a great time. Check in directions were clear and concise and were easy to follow. If you are looking for a great place to stay in Chattanooga that is comfortable, clean, and close to everything then look no further. You won’t regret it. My wife and I are looking forward to staying here again in the near future!

We had a fantastic stay! Logan was incredibly accommodating—responsive, friendly, and made check-in and check-out super easy. The place itself was spotless and clearly well taken care of, which made it feel really comfortable and welcoming. The location was also perfect—close to so many restaurants, coffee shops, and bars and in a great neighborhood. I would absolutely stay here again and highly recommend it to anyone looking for a clean, convenient, and hassle-free stay.

Location was amazing. Close to downtown Chattanooga and just far enough away where you can relax. Gary communication was fantastic

This was our second stay at Chad’s condo. It was perfect for us last year and remains that way. Chattanooga is a great city with lots to do and the central location of Chad’s place makes it convenient for walking and driving around the city and surrounding areas. The condo is well-furnished and the beds and furniture are comfortable. There is plenty of space for everyone to relax and it is so nice to be able to do laundry. Our family of four highly recommends Chad’s condo!

It was my first time in Chattanooga and this was the perfect place to stay! We visited for a few days during the week and Katie’s place was absolutely perfect for our needs. Clean, wonderful bathroom and kitchen, great location that was just down the road from a beautiful coffee shop and walkable to so many things. Her thorough instructions and house guidebook / manual were greatly appreciated. The space itself is clean, beautiful, cozy and modern. We felt right at home. I would absolutely recommend Katie’s space, thanks for everything!

A truly wonderful experience - fabulous, funky decor, walkable to everything we needed, comfy bedding & friendly, responsive service. Highest recommendation & many thanks!

Jennifer’s place was by far the best AirBnB we’ve ever stayed at. Super cute and cozy, well stocked (even had candy and snacks!), walkable distance to so much! The vibes of the studio were immaculate - whoever designed it knew exactly what they were doing. It’s beautiful! The no checkout instructions were also a game changer. Will stay here every time we come back to Chattanooga!

Had a great stay. Bed was comfortable. We had something come up and needed to stay an extra nite. The condo wasn’t booked and they made it seamless to add another nite. And walked across the street to Parkway Pourhouse which was a neat good restaurant.