Holiday rentals with a pool in Winchester

Lakefront Haven | Hot Tub | Kayaks, Firepit

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 • Hot Tub • Fantastic community pool for the hot summer days • Screened in, heated porch with TV and sound system • Kayak, 2 Paddleboards 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

Private indoor pool & sauna

Forget your worries in this spacious and serene space. Enjoy your own private indoor pool and sauna. Relax on the porch, grill up some great grub and enjoy time with family and friends. Only 3.2 miles to Jack Daniel Distillery and 13 minutes to Tims Ford State Park. Situated close to Tullahoma, Lynchburg and Shelbyville, TN. Lots to see and do. There are nearby hiking trails, waterfalls to explore, rent or bring your kayaks and float the Duck River. Tour several distilleries nearby.

Elk Ridge Cabin – Private Hot Tub & Stunning Views

Perched atop a scenic bluff in Bryant, AL, Grant Summit Cabins offers nine charming cabins overlooking Nickajack Lake. Each cabin features panoramic mountain and water views. With a variety of layouts and sleeping capacities, there’s something perfect for romantic getaways, family vacations, or group retreats. Whether you're sipping coffee on the porch or exploring the nearby hiking trails, relaxation comes easily here. Grant Summit Cabins blends comfort & nature for an unforgettable stay.

Barefoot Breeze

Enjoy lake living at one of the newest lakefront neighborhoods on Tim's Ford Lake. This beautifully decorated home is in a great gated community and sits very close to the lake. It is only a 1 min walk to the community pool overlooking the lake and direct lake access for 4 kayaks that we include for you! The home boasts indoor/outdoor fireplaces and outdoor seating for your family and friends to enjoy! You are also centrally located and only 5 minutes from Twin Creeks Marina and downtown!

Multi Family Treehouse! Hot Tub|Sauna|Theatre

Our unique experience isn’t easy to find — and it books quickly! Create memories, reconnect with your people, and escape the noise at one of the few properties within driving distance of Nashville, Chattanooga, and Huntsville. Imagine watching deer wander past the sauna window after a hike on one of 30 nearby trails just minutes from our private 5-acre retreat. Imagine sipping a glass of wine in the hot tub or a margarita in the plunge pool while the kids play ping pong just steps away.

Cliffside Infinity Pool • Hot Tub • Epic Views

Perched dramatically on the edge of a mountain, this one-of-a-kind luxury retreat offers sweeping, unobstructed views that will leave you breathless. Whether you're soaking in the private hot tub under the stars, lounging poolside by the infinity edge, or simply relaxing on the expansive patio with unforgettable views and sunsets, this is the escape you've been dreaming of. We are remote enough for peace, but close enough to mountains for adventure or Chattanooga for city entertainment.

Barefoot Dreams

Barefoot Dreams is a newer custom lake home vacation rental in the gated community of Barefoot Bay on Tims Ford Lake in Winchester TN. This luxury lake house rental is perfect for families and groups seeking a Tims Ford Lake cabin, waterfront getaway, or Tennessee lake vacation home. Enjoy stunning water views, modern design, and an open-concept layout. Ideal for boating, fishing, swimming, and lakefront relaxation. A peaceful yet fun-filled family vacation rental on the lake.

The Modern Mainstay at Barefoot Bay

Welcome to The Modern Mainstay, your stylish retreat by the shores of Tims Ford Lake! This pet friendly contemporary home is just 1/2 mile from the historic downtown square where you can enjoy doing a bit of shopping or dining. Or sit on the front porch with lake views, and take in the serene surroundings. Take a dip in our lakefront community pool. Enjoy access to the lakefront common area for fishing, swimming in the lake, and relaxing by the fire pit with a glass of wine.

TC Easy Breeezee

Your home away from home a place to enjoy friends and family together under one roof, relax and enjoy, kick back and forget all your worries! We have you covered, awning for protection of sun and rain! Warm cozy beds and sofas! New furnishing throughout entire house!! Sip coffee, on our cozy outdoor furniture while listening to the pool bubblers take all your daily worries away!! Unplug, sit back and find your happy place Close to shopping, marina, dining and much more

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.

Basecamp Retreat TimsFordLake

Welcome to Basecamp Retreat! Modern lake luxury on Tims Ford Lake. This 3-bedroom, 2.5 bath cozy retreat, located in the gated community of Barefoot Bay, is the perfect home base for your visit. Offering modern comforts and convenience in a prime location with picturesque lake views, Basecamp provides a comfortable and inviting space to relax and recharge. Located 2 miles from Twin Creeks Marina & Resort and 1 mile from downtown Winchester.

Luxe 2BR Cabin C by MHM Luxury Properties

Unwind in this charming Prairie School–style cottage nestled in Jasper Highlands, offering a cozy escape with thoughtful amenities, inviting living spaces, and a tranquil setting close to local attractions and outdoor adventures. - Just a 1-minute walk to Top of the Rock Brewery & Wedding Venue - 7-minute drive to Sweetens Cove - Only 30 minutes from Downtown Chattanooga Ready for a Jasper escape? Book your dates today!