Holiday rentals with a pool in Winchester

5 out of 5 average rating, 70 reviews

Treehouse in Sewanee

5 Acres! Cozy Nature Retreat

Imagine sipping your coffee while watching the deer pass through 5 acres of forest from our steam sauna. Imagine enjoying a private marked path on property or hopping in your car to hike a 9 mile, 5 hour trail just 15 min from home, then recovering in the hot tub. If you want a private city escape, our shipping container treehouse is for you! PRIVACY NOTE: There are ZERO shared spaces, no on else on property. While we live in a 'neighborhood' you cannot see another home from our treehouse.

5 out of 5 average rating, 41 reviews

Lakefront Haven–Fall Escape w/ Firepits + Kayak

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

4.89 out of 5 average rating, 127 reviews

Cabin in Bryant

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.

5 out of 5 average rating, 5 reviews

Home in Chattanooga

Cliffside Luxe Retreat w/Pool, Hot Tub, 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.

4.98 out of 5 average rating, 173 reviews

Guest suite in Trenton

Fall Vibes- Spa & Fire Place | Mins to Chattanooga

"Paradise. We could not have asked for more. The house was beautiful and stocked with everything we needed... The pool and hot tub were so relaxing." - Heidi Nestled in the heart of nature's grandeur in the North Georgia mountains, this beautiful suite offers comfort and awe-inspiring views. It's a sanctuary where modern luxury meets the tranquility of the great outdoors. "The place was incredibly cozy and peaceful, creating the perfect atmosphere for a relaxing getaway." - Courtney

4.98 out of 5 average rating, 50 reviews

Barefoot Retreat w/kayaks/SUP/Game Room/Pool

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

5 out of 5 average rating, 34 reviews

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.

4.91 out of 5 average rating, 22 reviews

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

4.95 out of 5 average rating, 22 reviews

Barefoot Bungalow Bright airy lakeside home

Relax in this beautiful lakeside home in Barefoot Bay. Gated community with its own pool and kayak launch. Enjoy views of Tim’s Ford Lake while being conveniently located near downtown Winchester. Spacious open concept kitchen, living and dining area with fireplace. One bedroom and full bathroom downstairs. Three bedrooms and 2 full baths upstairs with bunks in one room. Fire pit, along with kayaks and paddle boards for your pleasure and 2.3 miles to Twin Creeks Marina.

4.93 out of 5 average rating, 132 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.

4.93 out of 5 average rating, 60 reviews

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.