Kid-friendly vacation rentals in Winchester

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Popular amenities for Winchester kid-friendly rentals

Kid-friendly house rentals

Top guest favorite
The exterior of the property features a traditional single-story home with a welcoming porch and a spacious front yard. A covered carport is adjacent to the house, providing shelter. Lush green trees frame the scenic view, enhancing the overall appeal of the property.
Home in Estill Springs
5 out of 5 average rating, 13 reviews

Timberhill Home-Walk to the Lake!

NoyRating, 5 stars2 weeks ago
This place was exactly as listed and was very comfortable and cozy! The location was great and we had a great time staying here with my family 😊
Guest favorite
A two-story house is set in a green landscape, featuring a welcoming porch with a railing. The exterior is painted in warm tones, complemented by a distinctive metal roof. Large windows provide natural light, while nearby greenery enhances the peaceful environment.
Home in Bridgeport
4.89 out of 5 average rating, 85 reviews

Little Red Cabin

BrandonRating, 5 stars1 month ago
This was the second time I stayed here. It was close to my work. Also very nice and peaceful location. If I come back that way this is where I’ll stay.
Top guest favorite
A wooden dock extends over tranquil waters, framed by green trees in the background. Blue skies with fluffy white clouds are reflected on the lake's surface, creating a serene atmosphere for relaxation and waterfront activities.
Home in Estill Springs
5 out of 5 average rating, 72 reviews

Lakeside Paradise - Waterfront View & Private Dock

BrandyRating, 5 stars2 weeks ago
This was a great place. The boat ramp was super close and the covered boat dock was great. The house was clean with plenty of room for my mom's 70 birthday celebration and Memorial Day (the 9pm neighborhood curfew would have been nice to know prior to booking but we made it work). The description and pictures were exact as shown and described. We are definitely gonna to book again in the near future. Great job Derek!!!
Guest favorite
A rustic log cabin is set within a spacious green yard, surrounded by trees. A gravel path leads to the entrance, with stairs ascending to the front porch. Windows provide views of the natural landscape, reflecting a serene outdoor environment.
Home in South Pittsburg
4.89 out of 5 average rating, 452 reviews

Martin Springs Cabin.

JohnRating, 5 stars1 week ago
My wife and I stayed here for our honeymoon and it was absolutely perfect. The location is great as it is close to hiking areas, restaurants, and Chattanooga without being too busy! The house itself was beautiful inside and out. It was clean and tidy, the beds were comfortable, and it was stocked with anything we could have needed. The hot tub was extremely nice and clean. It was very spacious. The sound of the interstate was not bad once you got inside and if you are a light sleeper, David provided ear plugs and white noise machines to cover the sound of the interstate. However, the interstate sounds should not deter you from this stay because the house, host, and location are all excellent and outweigh the noise. 100% recommend and will be staying here again.
Top guest favorite
A spacious deck is viewed at dusk, lined with chairs facing a breathtaking sunset. Eight-foot windows reflect vibrant colors of the sky, while trees outline the horizon, providing a serene setting for relaxation.
Home in Lookout Mountain
4.98 out of 5 average rating, 229 reviews

The Lookout Mountain Birdhouse

DavidRating, 5 stars1 week ago
Lookout Mountain Birdhouse is a new property, so everything is shiny and clean. While just off the road, it's very private. It's ~30 minutes to Chattanooga proper, but that worked OK for us. Lacy is a true gem of a host and great to work with. She promptly answered any questions we had and stayed in touch. The good and the bad: the tall, west-facing windows make for a bright house and a beautiful view, but the windows in the living area have no shades, which can render that area almost unusable in the late afternoon on a clear day. That said, we would definitely stay there again. We particularly enjoyed the Sunset Rock via Craven's House Trail, and the Montague Sculpture Garden in Chattanooga. The tour of Chattanooga Whiskey Experimental Distillery was fun, too.
Guest favorite
A serene outdoor area is displayed with a fire pit surrounded by four wooden chairs. Lush green grass and trees provide shade, while the water of Tims Ford Lake glimmers in the background. A private dock is visible, enhancing the lakefront experience.
Home in Estill Springs
5 out of 5 average rating, 22 reviews

Just a short path to the lake! Private dock!

BethRating, 5 stars6 days ago
Great for a family gathering! Rain or shine, great places to hang out! Everything we needed! We would book again!
Guest favorite
The exterior of a modern two-story house is presented, featuring light gray siding and a white panel accent. A neatly landscaped front yard includes shrubs and a concrete walkway leading to the entrance. Bright blue skies and scattered clouds create a serene backdrop.
Home in Winchester
4.95 out of 5 average rating, 20 reviews

Barefoot Bungalow Bright airy lakeside home

ChristinaRating, 5 stars2 weeks ago
The house is great, liked just the photos and has plenty of supplies. The only thing that could make it better would be being closer to the lake!
Guest favorite
A tranquil scene depicts the calm waters of a lake surrounded by lush greenery. A wooden dock extends into the water, with a floating dock visible nearby. The area is shaded by trees, creating a peaceful retreat.
Home in Winchester
5 out of 5 average rating, 12 reviews

Lakefront 2 bed 2 bath lakehouse in private cove

DestinieRating, 5 stars1 week ago
Beautiful home! Everything was clean and well stocked. The only hiccup was the stairs to the dock - they are currently under construction but we were still able to maneuver around. We will be back to stay!

Kid-friendly apartment rentals

Guest favorite
An open-concept studio suite features a spacious layout with wood flooring. A king-sized bed is positioned against the wall, complemented by bedside lamps. A comfortable leather sofa and round table occupy the seating area, while kitchen appliances are visible on a nearby shelf.
Apartment in Monteagle
4.86 out of 5 average rating, 42 reviews

Adorable Suite Near the Caverns!

ShannonRating, 5 stars1 week ago
exactly as listed. enjoyed a show at the Caverns, and this was an easy drive from there. The only local food is a taco bell attached to a gas station, so plan accordingly if you're going to need food before you get there
Guest favorite
A spacious bedroom/living room combination is featured, marked by wooden beams overhead. A queen-sized bed is positioned near a wooden dresser and a decorative wall featuring plates. A cozy seating area with a couch and a lantern adds warmth, while a window with plantation shutters allows natural light.
Apartment in Lookout Mountain
4.9 out of 5 average rating, 525 reviews

Mockingbird Cottage on Lookout Mountain, GA

JackRating, 5 stars3 weeks ago
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.
Top guest favorite
A modern living area is presented with a sleek black leather sofa featuring two patterned pillows. Two comfortable armchairs flank a textured area rug, while a floor lamp provides soft illumination in the corner. The walls are a combination of white shiplap and dark accents.
Apartment in Winchester
4.96 out of 5 average rating, 28 reviews

Unbeatable Charm & Convenience On The Square!

Jorge L.Rating, 5 stars2 weeks ago
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.
Guest favorite
A dining area features a round table surrounded by four chairs, with a cozy bench attached to the wall. The space is adorned with patterned wallpaper and illuminated by two hanging light fixtures. A wooden staircase is visible in the background.
Apartment in Wildwood
4.87 out of 5 average rating, 137 reviews

Unique Condo on flight park! Watch hangliders fly!

RachelRating, 5 stars2 weeks ago
The property was as described, hosts were very communicative and the on site caretakers were very kind. Was very cool to watch the hangliders so close to the property
Top guest favorite
An inviting living room features a selection of classic arcade game machines, colored in vibrant hues. The walls are adorned with various artwork pieces, showcasing landscapes and stylized designs. A cozy seating area is positioned nearby, complementing the playful atmosphere.
Apartment in Winchester
5 out of 5 average rating, 9 reviews

Winchester Nomad Downtown Suites On The Square!

RebeccaRating, 5 stars2 weeks ago
Great place to stay for the wedding we attended at Twin Creeks. Close to everything. Walnut Hill is great for coffee every morning. We would stay here again.
Top guest favorite
A cozy guesthouse is situated on a gently sloped lawn, featuring a red metal roof and light brown exterior. A spacious wooden deck with steps offers outdoor seating. Large windows allow for abundant natural light, enhancing the inviting atmosphere of the home.
Apartment in Lookout Mountain
4.98 out of 5 average rating, 183 reviews

Rock Creek Guesthouse

LeslieRating, 5 stars5 days ago
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.
Top guest favorite
Apartment in Winchester
5 out of 5 average rating, 10 reviews

Hook, Wine, Sinker Unit B

ChristopherRating, 5 stars1 month ago
loved how accommodating the team was. got a welcome phone call right before I arrived which made me feel appreciated. the place was amazing. my group is already talking about planning the next trip here
Superhost
A spacious living area features modern furnishings with dark sofas and light wooden accents. Natural light filters through large windows, illuminating a dining table and an open kitchen equipped with essential appliances. A staircase leads to the upper level, enhancing the room's vertical space.
Apartment in Wildwood
4.79 out of 5 average rating, 91 reviews

Mountain Gliders Getaway Loft

SeanRating, 5 stars1 week ago
Very comfortable

Kid-friendly condo rentals

Guest favorite
A spacious deck overlooking the Tennessee River features white wicker chairs and small tables. Lush green hills frame the serene waterway, under a clear blue sky with scattered clouds, inviting relaxation and enjoyment of the natural surroundings.
Condo in Chattanooga
4.92 out of 5 average rating, 257 reviews

Water Front Outdoor Paradise 10 Min From Chatt!!

TaylorRating, 5 stars1 month ago
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!
Superhost
This private room features one full bed and one twin bed, with a dresser and desk positioned along the wooden walls. A bedside lamp provides soft illumination, and a ceiling fan is mounted above. A window allows natural light to enter, enhancing the cozy atmosphere.
Private room in Tracy City
4.7 out of 5 average rating, 10 reviews

Goat Pen Hostel - Gizzard South

MatthewRating, 5 stars2 months ago
This was a great stay! As advertised, and with lots of resources to explore the area. We were only staying one night as part of a roadtrip, so we didn't get to experience the area, but the place was very comfortable.
Superhost
A wooden staircase leads down from a second-floor entrance, showcasing natural wood railings. Sunlight filters through surrounding trees, casting gentle shadows on the steps. A grassy area is visible below, with a patio that features outdoor furniture in the background.
Condo in South Pittsburg
4.9 out of 5 average rating, 29 reviews

Cozy & private

BrookeRating, 5 stars5 months ago
This was our third stay, and it has been satisfying to see the investments made in the property over time. First there was the addition of outdoor amenities like a picnic table, grill, and lights. This time we noticed upgrades like a new mattress, TV, and coffee table. The hosts were super responsive, too, when something came up. We look forward to seeing what’s next!
Superhost
An open concept loft is featured with wooden accents and green walls, showcasing a staircase leading to the second floor. A fully equipped kitchen is visible in the background, adjacent to a cozy seating area, creating a welcoming atmosphere for guests.
Condo in Wildwood
4.81 out of 5 average rating, 72 reviews

Landing Zone Loft: Full Kitchen, Mountain Views!

JohnRating, 5 stars1 week ago
Communication with Dan prior to arrival was superb. We needed to make several date changes and Dan was not only incredibly flexible, but always responded more quickly than I expected. Better lighting and comfortable seating for two would be desirable improvements.
Top guest favorite
A private balcony features a small table and chairs overlooking the Tennessee River. Lush greenery and rolling hills are visible in the background, while a boat dock is situated along the water's edge.
Condo in Chattanooga
5 out of 5 average rating, 52 reviews

NEW Waterfront-Dock-Kayaks-SUPS- TN River Gorge

Calvin EugeneRating, 5 stars2 weeks ago
We absolutely enjoyed our stay. Dana was very friendly and helpful. Her home was beautiful and so peaceful. The perfect place to get away and enjoy some quiet. My husband had a wonderful birthday thanks to Dana and Scott! 11/10 ! We hope to stay there again

Quick stats about vacation rentals that are kid-friendly in Winchester

  • Total rentals

    40 properties

  • Nightly prices starting at

    G$10,457 GYD before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    20 properties have a pool

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