Family-friendly vacation rentals in Winchester

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Winchester family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
The cabin is positioned with a front porch featuring multiple seating options, including pink chairs. The exterior showcases a blend of grey siding and a metal roof. Surrounding trees provide a natural setting, while the driveway leads to the entrance.
Cabin in Bryant
4.93 out of 5 average rating, 87 reviews

Tri-state Corner Cabin with a fire pit, hot tub, &

JenniferRating, 5 stars3 weeks ago
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.
Superhost
The cabin's exterior is showcased, featuring two levels with a peaked roof and star accents. Spacious porches allow for seating and relaxation. Surrounding trees enhance the natural setting, while a gravel path leads to the entrance, providing access to the outdoor space.
Cabin in Bryant
4.88 out of 5 average rating, 114 reviews

Cloud 9 Cabin with an indoor pool, hot tub, & fire

BrookeRating, 5 stars2 weeks ago
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!
Guest favorite
The entrance to Paradise Pointe is marked by a stone sign, surrounded by natural landscape and mature trees. The driveway curves gently, leading to multiple cabins nestled on a mountain. A clear blue sky enhances the serene environment.
Cabin in Bryant
4.96 out of 5 average rating, 170 reviews

Pop & Granny's cabin with a fire pit, hot tub, & i

GlendaRating, 5 stars3 weeks ago
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!
Superhost
The exterior of the cabin is showcased against a backdrop of trees and blue sky. A spacious porch features seating, while a hot tub and fire pit are positioned on the manicured lawn. A wide driveway leads to an open area for parking.
Cabin in Bryant
4.92 out of 5 average rating, 116 reviews

Sunset Ridge cabin 21 miles from Chatt, TN! Indoor

NatashiaRating, 5 stars1 month ago
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!
Guest favorite
A hot tub is seen on a wooden deck, surrounded by trees and offering views of the lake in the distance. Nearby, cabin structures with metal roofs are visible, blending with the natural landscape under a clear blue sky.
Cabin in Bryant
4.98 out of 5 average rating, 89 reviews

WILDFLOWER CABIN, NO SUNDAY CHECK INS, HOT TUB

AshleyRating, 5 stars1 month ago
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 !!
Superhost
The three-story cabin features a modern design with multiple large windows allowing natural light. A wooden deck with railings leads to the entrance, surrounded by greenery. The exterior showcases a metal roof and natural materials, integrating the structure with its mountain surroundings.
Cabin in Bryant
4.87 out of 5 average rating, 68 reviews

Cabin in the Sky with an outdoor kitchen!

NicoleRating, 5 stars1 week ago
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.
Guest favorite
Home in South Pittsburg
4.89 out of 5 average rating, 445 reviews

Martin Springs Cabin.

CrystalRating, 5 stars4 weeks ago
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.
Superhost
The exterior of the cabin showcases a two-story structure set amidst trees. A spacious deck is visible, along with a drive leading to the entrance. A fire pit is positioned in the foreground, offering a cozy outdoor gathering space.
Cabin in Bryant
4.92 out of 5 average rating, 85 reviews

Rivers Ledge Cabin with breathtaking views, hot tu

NicoleRating, 5 stars3 months ago
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

Top guest favorite
An entryway framed by a wooden arch covered in green vines leads to a rustic red screen door. A path of natural stone pavers provides access to the door, surrounded by lush greenery.
Home in Beersheba Springs
4.96 out of 5 average rating, 69 reviews

The McGee Cottage in Beersheba Springs, TN

LindaRating, 5 stars5 months ago
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!
Guest favorite
Cabin in Beersheba Springs
4.91 out of 5 average rating, 75 reviews

Private Cabin Overlooking Savage Gulf State Park

StacyRating, 5 stars4 months ago
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.
Guest favorite
A rustic cabin is displayed, featuring a front porch lined with chairs and a table. The structure showcases wooden siding and a green metal roof, surrounded by lush grass and shady trees. Multiple windows allow natural light to brighten the welcoming exterior.
Cabin in Tracy City
4.85 out of 5 average rating, 336 reviews

Moonshine Runners Cabin

DanielRating, 5 stars2 weeks ago
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.
Guest favorite
A charming log cabin is set against a clear blue sky. Flowering shrubs in vibrant colors line the entrance, while a gravel pathway leads up to the welcoming porch. Large windows allow for natural light, and a small air conditioning unit is visible on the side.
Cabin in Tracy City
4.93 out of 5 average rating, 388 reviews

Log Cabin on 50' Miller's Falls - Eco-Village

LauraRating, 5 stars3 weeks ago
We enjoyed our stay very much in the cabin! The area was quiet, remote and just what we wanted.
Superhost
A compact bathroom features a light-colored wall with a full-sized vanity sink and wooden cabinets. A round mirror reflects the soft lighting. A shower curtain with patterned accents hangs nearby, while a white toilet is positioned against the wall, creating a functional and tidy space.
Cabin in Tracy City
4.91 out of 5 average rating, 380 reviews

Eco Container Cabin

DonnaRating, 5 stars3 weeks ago
Feel like we got the star treatment…arrived later than expected so we got a Gator ride to the falls with a personal tour.
The view from the deck features a calm lake bordered by lush greenery and trees. A two-story dock is visible at the water's edge, providing opportunities for boating and fishing. Soft sunlight filters through the leaves, enhancing the natural surroundings.
Home in Winchester
4.82 out of 5 average rating, 84 reviews

ONLY 30 steps to the Lake! Quiet Secluded Private

MadilynRating, 5 stars19 months ago
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!
Guest favorite
The entrance to the Carriage House is framed by wooden siding and features a glass-paneled door with a decorative mat. A small plant arrangement adds a touch of greenery beside the steps, and outdoor lighting fixtures are mounted beside the door.
Apartment in Tracy City
4.94 out of 5 average rating, 118 reviews

Carriage House Farm

RachelRating, 5 stars5 months ago
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!
Top guest favorite
A wooden dock extends into the calm waters of Tims Ford Lake, surrounded by lush greenery. Stairs lead down from a path to the dock, with rocky shoreline visible nearby. A boat can be seen in the distance, framing a serene lakeside view.
Cabin in Lynchburg
4.96 out of 5 average rating, 185 reviews

Cozy Cabin on Tims Ford Lake

RobertRating, 5 stars1 week ago
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

Superhost
An indoor pool area is featured with a spacious swimming pool surrounded by large stone walls. Colorful pool floats are present in the water, and a well-lit ceiling with decorative lights adds to the ambiance. Several chairs and a recreational table are visible in the background.
Cabin in Bryant
4.93 out of 5 average rating, 87 reviews

Tri-state Corner Cabin with a fire pit, hot tub, &

JenniferRating, 5 stars3 weeks ago
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.
Superhost
The exterior of the cabin showcases a two-story structure set amidst trees. A spacious deck is visible, along with a drive leading to the entrance. A fire pit is positioned in the foreground, offering a cozy outdoor gathering space.
Cabin in Bryant
4.92 out of 5 average rating, 85 reviews

Rivers Ledge Cabin with breathtaking views, hot tu

NicoleRating, 5 stars3 months ago
Beautiful house. We enjoyed every bit of it. Effortless entry, lovely view. Perfect little get away. Would definitely recommend.
Superhost
The cabin's exterior is showcased, featuring two levels with a peaked roof and star accents. Spacious porches allow for seating and relaxation. Surrounding trees enhance the natural setting, while a gravel path leads to the entrance, providing access to the outdoor space.
Cabin in Bryant
4.88 out of 5 average rating, 114 reviews

Cloud 9 Cabin with an indoor pool, hot tub, & fire

BrookeRating, 5 stars2 weeks ago
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!
Guest favorite
The entrance to Paradise Pointe is marked by a stone sign, surrounded by natural landscape and mature trees. The driveway curves gently, leading to multiple cabins nestled on a mountain. A clear blue sky enhances the serene environment.
Cabin in Bryant
4.96 out of 5 average rating, 170 reviews

Pop & Granny's cabin with a fire pit, hot tub, & i

GlendaRating, 5 stars3 weeks ago
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!
Superhost
Cabin in Bryant
4.92 out of 5 average rating, 116 reviews

Sunset Ridge cabin 21 miles from Chatt, TN! Indoor

NatashiaRating, 5 stars1 month ago
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!
Superhost
The three-story cabin features a modern design with multiple large windows allowing natural light. A wooden deck with railings leads to the entrance, surrounded by greenery. The exterior showcases a metal roof and natural materials, integrating the structure with its mountain surroundings.
Cabin in Bryant
4.87 out of 5 average rating, 68 reviews

Cabin in the Sky with an outdoor kitchen!

NicoleRating, 5 stars1 week ago
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

Destinations to explore