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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Superhost

A comfortable living area is observed, featuring a light-colored sectional sofa and a dark wooden coffee table. Large windows provide natural light, while a rustic dining table and chairs are visible in the background. Decorative wall art and assorted accents highlight the cozy atmosphere.

Cabin in Winchester

4.85 out of 5 average rating, 197 reviews

Private Dock - Best Cabin Tims Ford Lake

Great cabin located directly on Tims Ford Lake. Cabin has been updated and includes nice, well stocked kitchen as well as a deck (with grill). Enjoy our dock - fish, swim and use our two kayaks, paddle board and a canoe. Plenty of space to tie your boat up to our dock in a mostly private cove. Please read the guest access section for more details on lake access. Close to some great attractions - Jack Daniels Distillery (19 mi), Bonnaroo (25 mi), Univ. of the South (19 mi), Winchester (5 mi)

Top guest favorite

The exterior of a modern two-story home is displayed, featuring a light-colored facade with black accents. A garage door complements the structure, while a decorative blue door offers an inviting entrance. The manicured lawn extends towards the serene lake visible in the background.

Home in Winchester

5 out of 5 average rating, 36 reviews

Lakefront Haven on Tims Ford w/ Kayak and SUP

Welcome to Lakefront Haven! This home offers a seamless blend of comfort and luxury, providing a retreat for a lakefront getaway. • Lakefront property + beautiful views • Spa Getaway • Fantastic community pool for the hot summer days • Screened in, heated porch with TV and sound system • Kayak, Paddleboard and Peleton provided • Deck with gas Weber grill • Backyard firepit with chairs • Well equipped kitchen • Less than two miles from Twin Creeks Marina • Walkable to the downtown Square

Top guest favorite

A modern tiny home is surrounded by open grass fields, featuring a welcoming porch with wooden steps. Large windows provide natural light, while the exterior showcases a black siding and a gable roof. A gravel path leads to the entrance, enhancing accessibility.

Tiny home in Winchester

5 out of 5 average rating, 50 reviews

Tiny House

You will feel right at home in this adorable Tiny Home with RV Hookups! This picture-perfect little cottage has a bedroom with queen size bed, full bath with tile walk-in shower, full kitchen with all of the amenities, and living room with queen size sleeper sofa. The back porch offers peace, quiet, and spectacular mountain views. This property is super convenient to Tims Ford Lake, The Caverns music venue, Jack Daniels Distillery, University of the South, and historic downtown Winchester.

Guest favorite

A welcoming porch area features vibrant red flooring, complemented by a metal table and chairs. A vintage mailbox stands prominently, while a grill and a chiminea add to the rustic charm. Potted plants are placed nearby, enhancing the outdoor living space.

Cabin in Estill Springs

4.95 out of 5 average rating, 273 reviews

Holliday Hide Away

1200 sq. ft. very rustic converted pole barn. The floors are stained concrete and the walls are rough saw mill hewn poplar boards. Located on 3 acres of beautiful well kept property. It does not border the lake but is surrounded by Tims Ford Lake and less than 5 minute drive to 3 boat docks and launches. Close to restaurants, shopping venues, hiking trails, water falls and golfing. Pool table, cornhole set, board games & cards in cabin. Visit historic Franklin County and surrounding areas.

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, 122 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!

Guest favorite

A lively scene unfolds at the dual-level private dock, where guests enjoy various water activities. Individuals are seen jumping from the dock into the lake, while others paddle nearby. Bright umbrellas provide shade, and boats rest on the water, enhancing the vibrant atmosphere.

Home in Winchester

4.94 out of 5 average rating, 49 reviews

Grand Lakeview: Double decker dock, Fire Pit, Spa

Escape to the Captain's Quarters, a charming lakeside sanctuary. Unwind in our multi-level retreat, featuring floor-to-ceiling windows, a gourmet kitchen, and serene master suites with enchanting lake views. Designed to accommodate large groups, this spacious home boasts six bedrooms, and offers a total of 11 beds, ensuring privacy and comfort. Indulge in the great outdoors with our private dock, a hot tub, and delightful amenities, all set against the backdrop of Tim's Ford Lake.

Superhost

A serene outdoor space features four red Adirondack chairs arranged around a circular stone fire pit. The scene is illuminated by the warm glow of the setting sun, casting soft light through the surrounding trees and reflecting on the tranquil lake in the background.

Home in Winchester

4.89 out of 5 average rating, 118 reviews

Dock on Lake! Walk to Downtown Shops/Rest/Movies!

Charming, *Pet Friendly* well-loved 1950s lake house on Tim’s Ford Lake. Walking distance to grocery and downtown movie theatre, boutiques, restaurants and library. Near Twin Creeks marina/restaurant where you can rent boats. While here, you can swim at the dock; play darts, checkers or fuse ball; go out on the lake; walk to the Oldham Theatre; go hiking in Tim’s Ford State Park or nearby Sewanee; go to the Tullahoma drive-in theatre; or visit nearby Jack Daniel’s distillery.

Top guest favorite

A modern structure features a sleek black exterior with wooden shutters. A covered porch is highlighted by two chairs and a potted plant, inviting relaxation. Lush greenery surrounds the home, providing a serene outdoor environment.

Home in Winchester

5 out of 5 average rating, 18 reviews

The Hangout on Heath Lane

Enjoy a peaceful experience at this centrally-located home. The Hangout is half a mile from the beautiful Twin Creeks Marina and 1 mile to historic downtown Winchester! Other local attractions include: -Grab a coffee and enjoy a tasty breakfast or lunch at Walnut Hill Coffee Shop -For a delicious, upscale dinner, be sure to visit Filo's Tavern -Head out for a tour and tasting at Jack Daniels Distillery -Grab some tickets to the Cavern's for a memorable concert experience.

Guest favorite

The modern Scandinavian-style cabin is viewed from above, showcasing its dark exterior. A spacious balcony features a hot tub and outdoor seating. Two guests are seen enjoying the outdoor space, with a surrounding landscape of grassy fields and trees.

Cabin in Decherd

4.97 out of 5 average rating, 347 reviews

Hot tub, game room, fire pit and a view!

This modern, Scandinavian style cabin, sits on 20 private acres at a 1360 ft. elevation. The style sets it apart from other cabins. It is 13 miles from The Caverns concert venue (about a 20 minute drive). The cabin is close to Sewanee, which has many hiking trails and is home to The University of the South (about 7 miles from our cabin/ a 16 minute drive.) Other local hiking and recreation options include the South Cumberland State Park and Tims Ford State Park.

Guest favorite

A private dock with a metal-roofed boat shelter is observed on the calm waters of Tims Ford Lake. A small boat is anchored nearby, with lush greenery lining the shore in the background. The scene captures the serenity of the lake environment.

Home in Winchester

4.92 out of 5 average rating, 130 reviews

WHATAVIEW Lakehouse and Dock on Tims Ford Lake

WHATAVIEW Lakehouse is a 3-story, architect-designed house with uninterrupted views of Tims Ford Lake, Goose Island and Maple Island. It offers spacious, air-conditioned accommodations for one or multiple families. With its private dock, this quiet part of the lake offers safe swimming, boating, skiing or tubing, and fishing right off of the dock. Spectacular sunsets and the expansive views combine to make WHATAVIEW a memorable place to spend your vacation.

Superhost

A charming farmhouse is set against a backdrop of open green space, featuring a covered front porch and large windows that provide natural light. The exterior is highlighted by a green metal roof and white siding, creating a welcoming presence in a serene rural setting.

Home in Winchester

4.82 out of 5 average rating, 131 reviews

Spacious 4BR/3BA Home Near Tims Ford Lake

Welcome to your beautifully renovated 1940s 4-bedroom, 3-bathroom vacation home near Tims Ford Lake! This spacious historic retreat comfortably sleeps 8 and offers everything you need for a relaxing getaway in Winchester, TN. Enjoy fast Wi-Fi, a Roku Smart TV, and a large private yard perfect for watching the sunrise from the back porch and sunset from the front. Large bedrooms, a cozy reading nook, and a spacious kitchen and living area awaits you!

Guest favorite

The exterior view showcases a Craftsman-style house bordered by a spacious deck. A wooden pergola arches over part of the deck, enhancing the outdoor living space. The yard features manicured grass and is enclosed by a black fence for added privacy.

Home in Winchester

4.93 out of 5 average rating, 126 reviews

Lovely Lake View Home at Twin Creeks Marina

This Craftsman-style, lake-view house is located in the private, gated lakeside community of Twin Creeks Village at scenic Tim's Ford Lake in Winchester, TN. It features an open floor plan with 4 bedrooms, 3 baths, game room, screened porch and huge deck overlooking the lake. Use the included golf cart to go to the swimming pools, marina, bar & grill or on-site convenience store. Information on boat & jet ski rentals are available at the marina shop.