Family-friendly holiday rentals in Winchester

Spacious Lakeside Retreat w/ Hot Tub & King Beds

Take it easy at this unique and tranquil getaway home. Our custom built tiny cabin has 744 sq ft of indoor living with two private bedrooms and 2 full baths. The loft is great for kids. Additional amenities include fireplace, dedicated working space and fully stocked kitchen. Outdoor area includes a large deck, fire pit, luxury hot tub and grill. Sits on 2 acres of wooded land & features a community lake down the street. If you have additional guests, ask about our tree house located next door.

Chalet 638 - state park, golf & The Caverns

Short walk to a state park with golfing. This first floor living space has a kitchen, walk-in closet, large wood fireplace, workout equipment, washer/dryer, grill, fire pit and lots of space. Old Stone Fort Archeological Park with multiple hiking trails, fishing, canoeing and a $9 a round golf course are seconds away. Close to I-24 this centrally located Tennessee property gives equal access from Nashville to Chattanooga. Explore parks, vineyards, distilleries and Tennessee history from here.

Twin Oaks tiny house at The Retreat at Waters Edge

Nestled among the oak trees on Monteagle mountain with amazing views of the Fiery Gizzard reservoir, Twin Oaks tiny house is the perfect getaway! Explore the outdoors on hiking trails that lead to waterfalls, see concerts and enjoy eateries, and it's all so easy to get to! Lots of glass that brings the outdoors in if you just want to relax. Each season brings its own unique perspective. Twin Oaks is truly a one-of-a-kind experience. Stay one night or stay a month, you'll love your time here!

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.

The Nest at The Retreat @ Deer Lick Falls

The Retreat offers a cozy cottage for down time & you have the option to hike trails down to falls area, socialize with other guests or sit and have your own Fire in our fire pit on the property and just relax! Local Restaurants minutes away, lake access 10 minutes away with beautiful woodsy setting perfect for getting away from the hustle of everyday life! Covered patio for relaxing and you can eat outdoors with a grill guests can use and a fully equipped kitchen if you choose to cook.

Lake Home, Dock, Theatre, Hot Tub, FirePit, Kayaks

Take it easy at this unique and tranquil getaway. This beautiful lake home is one of it's kind at Tim's Ford. The house is nestled in a quiet rural neighborhood with woods in the backyard. The dock is only a small golf cart ride away. Enjoy beautiful lake views at your own private dock! This house is equipped with an amazing home theatre system, game room, hot tub, fire pit, kayaks and plenty more amenities! Tim's Ford Dam is only one mile away and has a public boat launch for you :)

Modern Monteagle A-frame with Hot Tub

Welcome to Camp Mae, a Scandinavian inspired A-Frame stay in Monteagle, TN. Minimalist designed yet elegant, offering the perfect escape- minutes from the Fiery Gizzard hiking trail and Monteagle. Relax in the hot tub or gather around the fire pit. For eco-conscious travelers, we provide an electric car charger. Experience seclusion of the mountains while only minutes from world class hiking, local restaurants and shops. This retreat harmonizes luxury with nature in a serene setting.

Sweet Dee's Tiny Home

FEATURES A HOT TUB! Relax in style at Sweet Dee's (formerly listed as The Alexander), a luxury tiny home in the Retreat at Deer Lick Falls. Serene, tranquil, rustic, wooded setting with relaxation stations throughout the community. The Retreat at Deer Lick Falls is a gated luxury tiny home community in southeast Tennessee. The community is only 15 minutes from the University of the South in Sewanee. Guests of the Retreat also have access to Retreat at Waters Edge and it's lake.

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.

Airstream #97 at The Grove

Sleep in a vintage 1997 Airstream! Fully updated with modern comforts, #97 is nestled in our forest campground, the perfect spot for your laid back Mountain getaway. The Grove at Natural Bridge features 3 vintage Airstreams, a shared well appointed bathhouse and restrooms. Located just a short drive (2.2 miles) from The University of the South and walking distance to Natural Bridge State Park.

Creekside at Rutledge Falls

Cozy nest right on the creek. Lots of privacy. Hiking trails and Waterfalls nearby. Listen to the water from a porch swing overlooking the creek. We have a double recliner for movies and popcorn. This efficiency apartment has a private entrance with private covered porch and a full kitchen. Work area with Wi-Fi. Pets are welcome - must be free of fleas and ticks.

Cozy Tiny Home w/large deck, hot tub and firepit

The Trail House is perfectly placed among the trees with many tall windows to take in the gorgeous surroundings. The large 2-tiered deck has two separate sitting areas. Hot tub and firepit area…fire wood provided! 2 kayaks and 2 bikes for use! Do it all, do absolutely nothing, or a little of both here at the Trail House.