
Family-friendly vacation 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

Tri-state Corner Cabin with a fire pit, hot tub, &
We had a great stay here! Beautiful surroundings, clean and comfortable cabin and loved having our own hot tub! The indoor heated pool and hot tub for all guests was also a great feature! The host was very nice and responsive. We would recommend this for sure and will keep Paradise Pointe in mind if we are ever back in the area.

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
Wow, I can't say enough about the view! Absolutely beautiful area and cabin was super clean! It has a steep drive up to it but we had no issues! Thanks for a nice stay!

Sunset Ridge cabin 21 miles from Chatt, TN! Indoor
This was perfect for our trip! We were only a 15 min drive from a grocery store, but high enough in the mountains to feel secluded. The views were breathtaking and the tri-state trail was challenging but rewarding!

WILDFLOWER CABIN, NO SUNDAY CHECK INS, HOT TUB
I love this cabin . It was just what me and my husband needed for our weekend getaway . We enjoyed the firepit ,swing and especially the hot tub !! Host was very responsive ! Thank you for letting us stay and can't wait to come back !!

Cabin in the Sky with an outdoor kitchen!
Beautiful location! The cabin was clean and well stocked. The pool house was huge and a big hit with the kids. We loved having the private hot tub. It was a little cool all week so we didn’t realize utilize the outdoor kitchen but it was a great feature. One note- there is not really any storage space for your clothes but we just worked out of our suitcase.

Martin Springs Cabin.
I took my son who is 12 for a little Spring Break getaway, we had fun on the trail, enjoyed the property, my sons favorite was the Hot Tub. The cabin was beautiful inside and out. Very clean and it had everything that you could possibly need or want. We will definitely be coming back again. The host was very communicative and friendly, I couldn't have asked for a better place or a better host.

Rivers Ledge Cabin with breathtaking views, hot tu
Beautiful house. We enjoyed every bit of it. Effortless entry, lovely view. Perfect little get away. Would definitely recommend.
Family- and pet-friendly home rentals

The McGee Cottage in Beersheba Springs, TN
We love visiting the McGee Cottage. This was our second stay in Beersheba Springs and it was just what the doctor ordered. The cottage is homey and cozy and old-fashioned and there is a lovely walk just outside the door. The area is full of wonderful hikes, waterfalls, and mountain views, and the McGee Cottage is a great home base for exploring the area. The peace and quiet were restorative. We'll be back!

Private Cabin Overlooking Savage Gulf State Park
Beautiful view from the cabin deck; located just outside a quaint little town. Very well-stocked property. Perfect for our group of 7 adults and 2 children. Only challenge was keeping the interior warm enough; several nights the temps dipped into the 20s and the fireplace, space heaters, and window units struggled to keep the interior above 50 degrees.

Moonshine Runners Cabin
Let me start by saying, the cabin was incredible. Felt like stepping back in time. Very well done. Our host even dropped off fresh baked cinnamon rolls and cake for us. Excellent surprise. Now the rest of the story… My wife and I chose this location to escape from the storms in mid TN. Weather reports looked decent. 1:00 in the morning we were woke up to tornado warnings and then it hit. Horrible experience and terrifying to be in a strange place during a tornado but, the cabin survived and kept us safe. Cindy the host was in immediate contact with us making sure we were safe and her husband came in person to check on us. Our terrible experience has nothing to do with the property or the host, both were beyond fantastic and for that alone deserve your business. We will definitely be back hopefully when the weather is better. Thank you Cindy for being a caring and wonderful person. Mostly thankful for the cabin that did its job and kept my wife and I safe.

Log Cabin on 50' Miller's Falls - Eco-Village
We enjoyed our stay very much in the cabin! The area was quiet, remote and just what we wanted.

Eco Container Cabin
Feel like we got the star treatment…arrived later than expected so we got a Gator ride to the falls with a personal tour.

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!

Carriage House Farm
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!

Cozy Cabin on Tims Ford Lake
Great place for a relaxing stay. The cabin was stocked with everything you may need. Very thankful that pets were allowed to come with us.
Family-friendly home rentals with a pool

Tri-state Corner Cabin with a fire pit, hot tub, &
We had a great stay here! Beautiful surroundings, clean and comfortable cabin and loved having our own hot tub! The indoor heated pool and hot tub for all guests was also a great feature! The host was very nice and responsive. We would recommend this for sure and will keep Paradise Pointe in mind if we are ever back in the area.

Rivers Ledge Cabin with breathtaking views, hot tu
Beautiful house. We enjoyed every bit of it. Effortless entry, lovely view. Perfect little get away. Would definitely recommend.

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
Wow, I can't say enough about the view! Absolutely beautiful area and cabin was super clean! It has a steep drive up to it but we had no issues! Thanks for a nice stay!

Sunset Ridge cabin 21 miles from Chatt, TN! Indoor
This was perfect for our trip! We were only a 15 min drive from a grocery store, but high enough in the mountains to feel secluded. The views were breathtaking and the tri-state trail was challenging but rewarding!

Cabin in the Sky with an outdoor kitchen!
Beautiful location! The cabin was clean and well stocked. The pool house was huge and a big hit with the kids. We loved having the private hot tub. It was a little cool all week so we didn’t realize utilize the outdoor kitchen but it was a great feature. One note- there is not really any storage space for your clothes but we just worked out of our suitcase.
Quick stats about vacation rentals that are family-friendly in Winchester
Total rentals
110 properties
Nightly prices starting at
ﺩ.ﺇ184 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
- Sweetens Cove Golf Club
- Monte Sano State Park
- Chattanooga Golf and Country Club
- Black Creek Club
- The Ledges
- Coolidge Park
- Creative Discovery Museum
- The Lookout Mountain Club
- Chattanooga Choo Choo
- Kyujo-mae Station
- Old Fort Golf Course
- Hunter Museum of American Art
- National Medal of Honor Heritage Center