Vacation rentals with a pool in Winchester

5 out of 5 average rating, 58 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, 35 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

5 out of 5 average rating, 67 reviews

Cozy Lake Cottage W/Pool, Hot Tub,Kayaks, SUPs

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 has lake views from the front porch. 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 also boasts a hot tub, fire pit, and game room for your family to enjoy! You are also centrally located and only 5 min from Twin Creeks Marina and downtown!

5 out of 5 average rating, 10 reviews

The Old Fashioned @ Twin Creeks - FREE BOAT & POOL

*FREE BOAT - Any 2 or more nights booked and staying through July 31st, 2025 qualifies for one full day complimentary pontoon rental of your choosing, subject to terms & availability! This home offers a vintage vibe with a twist of sophistication. The Old Fashioned is equipped with a game room, poker tables & leather tufted sofas. Breathtaking views of Tims Ford Lake and Twin Creeks Marina right out your back door. Sit back and relax while you pour the bourbon here at the Old Fashioned.

5 out of 5 average rating, 26 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.

4.9 out of 5 average rating, 20 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

5 out of 5 average rating, 14 reviews

Perfect Lakefront Getaway! Pool, Fire Pit, Marina

Relax with the whole family at this peaceful and stylish new construction home in a beautiful gated community. Gorgeous lake views abound! Simply walk outside your front door to enjoy beautiful Tims Ford Lake. Private community pool club with spacious saltwater pool overlooking the lake. Pamper yourself and relax in this spacious and stylish home made for the ultimate getaway! Next to Tims Ford Marina with boat and kayak rentals 7 days a week. Relax and unwind!!

4.93 out of 5 average rating, 124 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, 57 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.

4.96 out of 5 average rating, 174 reviews

Cabin in Bryant

Pop & Granny's cabin with a fire pit, hot tub, & i

SUNDAY check in ALLOWED. POP & GRANNY'S CABIN is located inside Paradise Pointe which is gated & on a mountain, tristate corner of AL/TN/GA. HIKING TRAIL to tristate corner. Paradise Pointe has 1 HuGe INDOOR POOL HOUSE with outdoor deck-19 rentals has access to pool house. WIFI, hot tub, fireplace, grill & fire pit! Main floor-BDR 1/king, Upstairs-BDR 2/king, BDR 3/family room/true queen bed & 2 recliners & BDR 4/king

4.88 out of 5 average rating, 17 reviews

Lakeview Luxe | Lake Access + Pool

Lakeview Luxe is a 3-bedroom, 2.5-bath retreat nestled in the gated Barefoot Bay community right on Tim’s Ford Lake. Enjoy lake views, access to a waterfront community pool, kayak launch and firepit, and a private fenced backyard with a cozy outdoor fireplace. Only a one minute walk to the lake and just one mile from charming downtown Winchester, you'll be minutes from great dining, shopping, and entertainment.