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 cabin features a combination of wood and stone exteriors, showcasing large triangular windows that allow for abundant natural light. A welcoming entryway is highlighted by a sturdy wooden staircase leading to an expansive deck surrounded by trees in a serene outdoor setting.

Cabin in Dunlap

4.91 out of 5 average rating, 235 reviews

Cagle Mountain Cabin near Fall Creek Falls Park TN

Quiet, comfortable and contemporary cabin on 7 acres, situated between three of the most beautiful parks in Tennessee: Fall Creek Falls, Savage Gulf and Rock Island State Park. We are pet friendly for a small additional fee. *** We have made the difficult decision to sell our cabin. Any accepted reservation will be honored, but it may be necessary to show the home to a potential buyer during your stay; you will be notified a minimum of 24-hours in advance if this happens during your stay. **

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, 264 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, 445 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.

Guest favorite

A modern bathroom features gray walls and a neutral-toned decorative rug. A shower stall with a curtain stands beside a vanity with a granite countertop, equipped with a mirror and ample lighting. A toilet is positioned near the entrance, creating a functional space.

Cabin in Dunlap

4.8 out of 5 average rating, 103 reviews

The cabin at Bluebell woods.

The view from this cabin is beautiful! Either sit on the living room couch or on the deck and enjoy the lovely view of the lake. It is situated on a level, wooded lot that is a great getaway. Perfect for paddle boarding, canoeing, kayaking, fishing, etc. We have a paddle boat and a flat bottom boat with a trolling motor for guests to use. In close vicinity to hiking, off-roading, paragliding, rock climbing and many other activities. Deerhead Lake in Dunlap is 55 mins from Chattanooga, TN.

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, 108 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, 118 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 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, 319 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.

Superhost

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

4.8 out of 5 average rating, 304 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 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, 143 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.

Guest favorite

A cabin balcony extends over a scenic lake view, framed by lush greenery. The water glistens under natural light, with rolling hills visible in the distance. The structure’s wood railing complements the surrounding landscape, creating a peaceful and serene environment.

Cabin in Bryant

4.88 out of 5 average rating, 102 reviews

Elk Ridge No Sunday Check In 25 mi fromChattanooga

WE DO NOT HAVE SUNDAY CHECK INS , I HAVE 9 CABINS IF THIS ONE IS BOOKED YOU CAN SEE OTHER AT WWW.GRANTSUMMITCABINS.COM you have all the amenities of home. real wood fireplace, hot tub, washer and dryer, full kitchen,amazing views, private, gated , i have 8 cabins close to each other. pictures just do not describe the quietness and serenity of the place. only 25 miles to downtown chattanooga tn. located on the tn ,ga, and alabama lines. we are not a bed and breakfast

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

A farm structure with rustic wooden walls is partially obscured by tall grass and trees. A gravel road leads to the building, framed by overgrown vegetation. Sunlight filters through the leaves, creating a natural glow around the scene.

Cottage in Fayetteville

4.97 out of 5 average rating, 231 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.