Vacation rentals with a pool in Winchester

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.

Lakefront Haven–Hot Tub & Heated Porch

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

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.

Luxurious New Build LakeHouse Tim’s Ford 4BR4Bath

Fully furnished - a unique Tim’s Ford 3 level house! 4 bedrooms LakeHouse with 3 decks, theatre room, 2 furnished kitchens. Free Kayaks with jackets. Soak in the Sun or feel the breeze from the three decks - with breathtaking views. Next door Swimming pool n boat ramp. Twin creek Marina n restaurant - 5 mins drive. Downtown Winchester restaurants - 5 min drive. 3 cars parking + guests parking. Wheel chair ramp access. Family n friends celebrate lake life at Lakehouse! Pls declare your pets

Lovin Lake Life

Relax and unwind at this spacious 5BR/7-bed townhome just 1-2 minutes from Twin Creeks Marina & Dry Creek Beach! Take the complimentary golf cart and relax by the pool or head to the marina to rent a boat, shop at the store, or eat/drink at Drafts & Watercrafts Bar & Grill. Enjoy cozy furnishings, relax on the screened in porch, or challenge your group to a game of ping pong. This home is perfect for families, groups, and lake lovers looking for a fun and easy getaway in Winchester, TN.

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.

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.

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.

Mountain High Cabin with hot tub, fire pit, & indo

Mountain High Cabin is located in Paradise Pointe, a gated mountain retreat at the tri-state corner of AL/TN/GA. Hike the trail to stand in three states at once! Enjoy access to the huge indoor pool house with a communal hot tub, two indoor slides, an outdoor deck, seating, and more. All 19 rentals share these amenities. Plus, enjoy two small basketball courts, sand volleyball, horseshoes, and more for endless fun!

Chic 2BR Cabin D by MHM Luxury Properties

Experience a luxurious getaway at this single-level cottage in Jasper, 30 minutes from Chattanooga, surrounded by beautiful mountain and river views. - A 1-minute walk to Top of the Rock Brewery & Wedding Venue - A 7-minute drive to Sweetens Cove - Just 30 minutes to Downtown Chattanooga Relax, unwind, and explore all that Jasper has to offer!

Stunning Lakefront! Pool, Kayaks, Bikes, Marina!

Experience pure luxury and lakefront living at its finest! Kick back and relax with the whole family in this stylish custom designed new construction- built to impress! All the finest amenities are also at your fingertips from Kayaks and Pool on site. Relax and have a luxurious adventure in this gorgeous getaway!!