
Family-friendly holiday rentals in Winchester
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Top-rated family-friendly rentals in Winchester
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
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Popular amenities for Winchester family-friendly rentals
Family-friendly home rentals with a hot tub

The Bedrock Cave Cottage
Magical and beautiful Bedrock Cottage! Clean, spacious, comfortable bed and pillows, WiFi and I loved visiting the koi fish pond that’s on this beautiful property. There’s a rooftop too! Watching hang gliders up in the sky was really cool! Rick is so welcoming and friendly, couldn’t ask for a nicer host! Absolutely loved our 3 nights stay!

5bdrm HotTub~18ppl STONE BROOK
Great place specifically if you have a larger group. Lots of outdoor activities, foosball, and ping pong! Host was very proactive, lots of instructions around the house that provide clarity of expectations. We enjoyed our time together!

The Cavern on the Green. Ancient architecture
I really enjoyed staying at this place! It was private and unique and Rick was a wonderful host

Best View In Chattanooga, Pet Friendly, 2BR 2BA
Beautiful home with an incredible sunrise view. You won't regret staying here. The home is clean and very well stocked. The area is very private and you can hear the waterfall below. You'll enjoy watching hummingbirds on the porch while sipping your coffee & taking in the beautiful sunrise. Great local lookout points, restaurants, coffee shop, and other attractions within 5-10 minutes from the house.

Lookout Mountain Brow Home. The Sunset House.
Peaceful stay, breathtaking views - very clean and everything needed was there to make our stay so easy! Highly recommended.

CABIN THERAPY❤RuralChattanooga CabinL❤Fresh HotTub
Home as described. Clean and tidy. Host have thought out recommendations for various services listed in a folder for their guests. Check in and out process exactly as described. Small but very functional getaway for my family. I would stay here again.
Family- and pet-friendly home rentals

The McGee Cottage in Beersheba Springs, TN
George was an excellent host. He met us at the cottage and very helpful in finding local interests. This place was an excellent location for hiking nearby trails. Be sure to check out the waterfalls as well. It’s also an hour and 15 minutes from Chattanooga. There is a DG Market in Altmont which is a great alternative to Walmart. A very peaceful setting and located on the edge of Savage Gulf State Natural Area. We enjoyed our stay at this place very much.

Private Cabin Overlooking Savage Gulf State Park
We had a great stay! Perfect get away weekend with friends. Fantastic view and had everything we needed.

The Cozy Little House
The house was exactly how it was described and shown in the pictures. It was a nice and quiet area and I felt right at home. 5/5, would book again. Thank you, Brandy!

Log Cabin Apt Lookout Mountain Fireplace King Bed
Honestly, I wish we got to stay longer than we did. It's a really pretty cabin with lots of wildlife around. There is a sweet cat that will come right up to your door, and break your heart when you leave. The only asterisk I have about the place is the height of things. My wife and I are both above 6 feet tall, and we hit our heads on multiple doorways. That's on us; we're first to know when it rains. That being said... If you're tall -- be prepared to duck.

Eco Container Cabin
we stayed in the Eco Container home. It was really cool. Our power went out from a bad thunderstorm storm but that was no problem because the container home was equipped with a solar powered battery back up. The location was very nice, remote but easy to find and just 10 minutes from town. Millers waterfall was beautiful and serene. Check out was very personal. We shared hiking stories and other stories of the property. I love this place. I would recommend to anyone who loves hiking and nature or just a place to relax and get away from the rat race.

ONLY 30 steps to the Lake! Quiet Secluded Private
Natalie was so nice! We were so grateful to get to celebrate my mom’s 50th birthday at this cool lake getaway. We appreciated the flexible check in time and all the local recommendations. The use of the boat dock and private ramp was huge for us as we love to be on the water. We hope to come back someday!

Private Cottage on Lookout Mountain
I would say better than advertised. Absolutely beautiful and warm cottage. One of the best views around awaiting you at the end of the driveway. Everything you want to do is a short drive away. I honestly didn't want to leave this place and will definitely book this place again the next time im in that area!

Lookout Mountain Bungalow Getaway
This home is excellent. Don’t hesitate to book. Extremely clean, beautifully decorated, quiet, and the host is amazing. I look forward to staying again, when we are in the area.
Family-friendly home rentals with a pool

Tri-state Corner Cabin with a fire pit, hot tub, &
Great place. Great value and great views. Enjoyed our stay!

Cloud 9 Cabin with an indoor pool, hot tub, & fire
Our family went out for a few days during spring break and it was awesome!! My girls loved all of the animals, the big indoor pool, and fishing!! We plan to come again! Fred was also super responsive and the place was so easy to find!

Pop & Granny's cabin with a fire pit, hot tub, & i
This was exactly what we were looking for-a clean, comfortable place with a beautiful view and mountain feel on our way to Savannah to visit family. The weather was perfect for one of the days, and the other day it was rainy and foggy, but we spent that day going to Ruby Falls. It cleared up in the afternoon. We spent evenings around the fire pit in which wood was provided and we brought our own outdoor chairs that were more comfortable than the benches provided. We also grilled out using the grill on the property, and there were plenty of silverware, dishes, glasses, pots and pans etc. Everything was just as pictured. All in all, a wonderful getaway. We would definitely stay here again. Thank you to Fred, our host.

Sunset Ridge cabin 21 miles from Chatt, TN! Indoor
This was a dream come true for our family! My kids were thrilled with their experience and couldn’t have been happier! My wife and I felt so much at peace and we loved the view. We felt so happy with our choice we booked an extra night and no one wanted to leave! Absolutely amazing!!

Cabin in the Sky with an outdoor kitchen!
The place was more than what we ever could have dreamed. Fred was super attentive and was willing to help with whatever we needed. The indoor pool was a hit for not only the kiddos but for the adults as well!! Would most definitely come back!

Rivers Ledge Cabin with breathtaking views, hot tu
Loved the stay it was a great place to go back to and relax the drive to get up is a bit steep but other than that it was great

Cozy home for up to 10 guests on LkMt GA
Great place. Was fast at responding to any questions we had.

Chatt Vistas Oasis-3bdrm-5m to TN-PoolDeckBBQFireP
The kids loved the pool! Very close to Rock City! We loved staying here wish we could have stayed longer.
Quick stats about holiday rentals that are family-friendly in Winchester
Total rentals
110 properties
Nightly prices starting at
₹4,328 before taxes and fees
Total number of reviews
2.9K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
70 properties have a dedicated workspace
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- Tennessee Aquarium
- Cloudland Canyon State Park
- Monte Sano State Park
- Sweetens Cove Golf Club
- Black Creek Club
- Chattanooga Golf and Country Club
- The Ledges
- Coolidge Park
- Chattanooga Choo Choo
- Creative Discovery Museum
- The Lookout Mountain Club
- Old Fort Golf Course
- National Medal of Honor Heritage Center
- Hunter Museum of American Art