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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Guest favorite

The charming exterior of a tiny mountain cabin is framed by lush greenery and vibrant pink flowers. A wooden porch with a railing provides access to the cabin, featuring a gas grill and a few outdoor chairs for relaxation.

Cabin in Morrison

4.93 out of 5 average rating, 269 reviews

Little Mountain Cabin Extraordinary Secluded View!

Secluded, PRIVATE tiny mountain cabin offers solace for your soul! Altamont, TN. Expansive mountain views from private front porch. ESCAPE the world. 20 mn to State Parks, hike, waterfalls. An awesome slice of heaven tucked on a mountainside. 1,000 acres of wilderness surrounds your cabin with stunning South Cumberland Mountain views. Pristine PRIVATE setting. Mountain sunrises. stars, moonrises. Serenity, peace. Refresh, restore. Charming cabin w/kitchen, loftbed, full bath. Firepit, heat/ac.

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, 454 reviews

Martin Springs Cabin.

This country cabin is a great base for exploring the nearby South Cumberland Park and surrounding area. Convenient to Sweetons Cove Gulf, The Caverns, Adventure Offroad Park, Sewanee, Monteagle, South Pittsburg/Cornbread Festival, Jasper Highlands. right next to I-24. You can't see any other homes from the cabin and adjacent meadow. Year round creek in the property. Meadow trail. New Hot Tub and all new Tuft & Needle mattresses for 2022! Basic amenities provided. Includes Wi-Fi and DVD player.

Superhost

The exterior of the hand-carved cave cottage is presented at dusk, with soft lighting highlighting the entrance. Lush greenery and colorful flowers surround the stone pathways, while the gentle slopes of the hill and distant mountains provide a scenic backdrop.

Bungalow in Wildwood

4.84 out of 5 average rating, 526 reviews

The Cavern on the Green. Ancient architecture

This hand-carved cave cottage has a beautiful exterior and gets even better as you go inside. Its well decorated cavern interior will charm you with its thoughtful layout. On the main floor there is a full kitchen with stone counters and dining bar, a sitting area with comfy chairs, a bathroom with an oversized tile shower, a bedroom with a queen bed and a private porch with a large hot tub. Up the stone steps you'll find a super cute bedroom loft with lots of windows and more amazing views.

Guest favorite

Lush green trees frame a peaceful view of the lake, where a floating dock is visible alongside moored boats. A paved pathway leads down to the water's edge, surrounded by manicured grass and natural stone. Clear blue skies reflect off the calm surface of the water.

Home in Winchester

4.94 out of 5 average rating, 110 reviews

Beautiful Tims Ford lakefront home

Beautiful 3 level lake front home right by the water with no steps to the dock. Plenty of room for large groups of people and great for families with kids. Five bedrooms with a bonus room that has plenty of extra beds. Located less than a mile from public boat ramp. Located in quiet cul-de-sac, on a cove with no wake next to the main channel. If there are any dates that are blocked off that you want please message us because we may have some blocked off dates that we can open up for you.

Top guest favorite

An outdoor seating area features blue and white lounge chairs arranged around a central fire pit. The shaded porch swing offers a serene view of the lake, framed by lush greenery. The dock and numerous boats can be seen in the background.

Home in Winchester

4.96 out of 5 average rating, 119 reviews

Private dock/gazebo on quiet cove. Tims Ford Lake!

Indulge in the tranquility of Tims Ford Lake, TN! Our exquisite 5-star cottage, just 6 miles from Tims Ford State Park/Marina, beckons you to unwind. Conveniently situated 18 miles from Tullahoma and 8 miles from Winchester, our boat-friendly haven features a private dock and a circular drive. Minimum rental age: 25. Ensure a seamless stay by signing our legal Rental Agreement and presenting a government-issued ID. Book now for a worry-free lakeside escape – your perfect retreat awaits!

Top guest favorite

A comfortable brown couch is positioned near a large window, offering a view of lush green foliage outside. A decorative pillow featuring a leaf design rests on the couch, adding a subtle touch of nature-themed decor. A round coffee table is visible in front.

Home in Chattanooga

4.97 out of 5 average rating, 360 reviews

Glenn Falls Retreat

For nature-lovers, with a waterfall view during the wet season, and spectacular treetop views during the dry season, the Glenn Falls Retreat is ready to host your next mountain getaway! Only a 4 mile drive to downtown Chattanooga where you can enjoy some of the best restaurants, art and music in the south; and only 4 miles to Rock City and Ruby Falls; the Glenn Falls Retreat is on a 2 acre wooded lot where you can explore the Lookout Mtn. trails and the year-round majesty of Tennessee.

Top guest favorite

A treehouse-style cabin stands elevated on stilts, surrounded by lush greenery. A spacious deck is visible at the front, offering an outdoor seating area. The roof has a distinct metal finish, enhancing the cabin's secluded nature. Trees provide natural shade around the structure.

Cabin in Altamont

4.97 out of 5 average rating, 322 reviews

Sunrise Mountain Tree House Cabin

Experience the fun of living among trees in our treehouse mini-lodge feel check out 2 other cabins Patriot's Retreat & Sunrise Mtn Cabin. Our tree house is extremely comfortable, with a view of the Cumberland mountains. Complete with a full kitchen, bathroom, two-loft sleeping and viewing areas. Several major state parks/hiking within a few miles of the cabin. Exceptional star viewing. The cabin has fiber optic WiFi which is not shared. Pet cats are not allowed as we are allergic.

Guest favorite

A charming cabin is set against a backdrop of lush woodlands, featuring a gabled roof and a welcoming porch. Warm light emanates from the windows, highlighting the inviting entrance. Two outdoor chairs are positioned on the porch, adding to the serene atmosphere.

Cabin in Chattanooga

4.81 out of 5 average rating, 309 reviews

Cozy Mountain Retreat w/ Spa

20 min. from downtown Chattanooga This cabin is surrounded by woodlands. Hiking trails, swimming holes and water falls abound here! End the day in the mountains gazing at the stars from the spa, or gathered around the fire roasting marshmallows. This adorable cabin sleeps 6 comfortably and provides a full kitchen, sleeping quarters separated by barn doors for the kids, and a private back yard with patio and grill for your enjoyment. No smoking or vaping NO KIDS ALLOWED IN HOT TUB

Top guest favorite

A view from the porch reveals the serene waters of Tims Ford Lake, bordered by lush greenery. The railing is partially visible, with sunlight filtering through the trees, creating dappled shadows on the deck. A bird feeder hangs nearby, inviting wildlife.

Cabin in Lynchburg

4.96 out of 5 average rating, 195 reviews

Cozy Cabin on Tims Ford Lake

Come stay at a hand built log cabin nestled right on Tims Ford Lake. Enjoy a cup of coffee and watch birds fly in a rocking chair on the front porch. Relax in the porch swing as you see fish jump from the water. Grill out on the back porch while watching the sun set. There is a dock available for fishing. The cabin is five miles from Tims Ford State Park, eight miles from Jack Daniels Distillery and downtown Lynchburg, eleven miles from Tullahoma, and fifteen miles from Winchester.

Top guest favorite

A serene view of Tims Ford Lake is framed by lush greenery, with sunlight reflecting off the calm water surface. The surrounding trees provide a sense of seclusion, enhancing the peaceful ambiance of the lakeside setting.

Home in Lynchburg

4.99 out of 5 average rating, 145 reviews

Southern Comfort Lakehouse on Tims Ford Lake

Tims Ford Lake is the best family vacation all year and we have the best view on the lake. We're on Lost Creek with 4 bedrooms, a bunk room, 3 full baths, game room, 2 large decks, a dock with a Hydrohoist and Jet Ski lift. Our cove is off the main channel so no direct boat traffic. It's 10 minutes from Jack Daniels Distillery and the State Park with hiking/biking trails and the fabulous Bear Trace Golf Course. We're on a cul-de-sac in a secluded neighborhood with the best sunsets.

Superhost

The exterior of a two-story cabin is seen, featuring a sloped roof and a welcoming front porch with two chairs. Surrounding the cabin, a well-maintained lawn and gravel pathway create an inviting atmosphere amidst a wooded landscape.

Cabin in Winchester

4.82 out of 5 average rating, 157 reviews

VACATION CABIN - Sunday Morning Rentals

We are in Winchester, TN, and are located within a SHORT 5 MINUTE WALKING DISTANCE to Tims Ford Lake and Devil Step Boat Launch. Sunday Mornings Rentals is a completely equipped cabin that ensures a relaxing getaway. Perfect for all of your boating, fishing, and hiking recreations. The charming town square is approximately 5 miles from the rental - offering unique shops, a quaint theatre, and restaurants that are sure to provide enjoyment for everyone. PETS NOT ALLOWED.

Top guest favorite

The exterior of the recently remodeled farmhouse is presented, featuring a blue color scheme and a covered porch. Lush greenery surrounds the home, with flower beds accentuating the landscape. A small tree with vibrant red leaves is visible near the entrance.

Cottage in Fayetteville

4.97 out of 5 average rating, 239 reviews

Country Cottage Hideaway near Lynchburg

Recently remodeled Farmhouse on a working goat farm. The rental does not include access to the Barn or farm land. Visiting Lynchburg? This is the perfect place to unplug and enjoy quiet country living. The property is tucked into a secluded country hollow and does not have any visible neighbors. Includes a large porch with a swing and a cozy fireplace to snug in front of on those chilly winter nights. Located 7 miles from Jack Daniel's and Downtown Lynchburg Tennessee.