Vacation rentals with a pool in Winchester

5 out of 5 average rating, 90 reviews

A shipping container home is surrounded by lush trees, featuring large windows that offer views of the forest. Natural light filters in, illuminating the interior space, which is thoughtfully designed to blend with the outdoor scenery.

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.

4.95 out of 5 average rating, 64 reviews

The retreat home is surrounded by trees, illuminated by soft outdoor lighting. The covered porch features string lights, enhancing the inviting ambiance. Large windows reveal a warm interior, while the steps lead to a well-defined path, blending nature with cozy outdoor living.

Cabin in Tracy City

Larger Home in Tiny Home Lake Community

Our home, Eagles Edge, is nestled on 2 wooded acres in a gated lake community-"Retreat at Water's Edge". Our community has a 95 acre calm water lake w/ kayak & bike rentals, docks, pavilion, fishing, fire pits, playground, trails & a pool(coming soon). Nearby: South Cumberland State Park w/ trailheads, waterfalls, hiking, biking (Mountain Goat Tr), Sewanee-University of the South (many trails), Monteagle, Tracy City, the Caverns-Pelham, Big Foot Adventure, Tim's Ford Lake, & Chattanooga.

The exterior of a modern two-story home is displayed, featuring a light-colored facade with black accents. A garage door complements the structure, while a decorative blue door offers an inviting entrance. The manicured lawn extends towards the serene lake visible in the background.

5 out of 5 average rating, 47 reviews

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

4.89 out of 5 average rating, 18 reviews

The welcoming exterior of a two-story farmhouse is shown, featuring a front porch with seating options. Lush greenery and hanging plants frame the entrance, complemented by a neatly manicured lawn. The light-colored siding contrasts with the dark accents of the porch, creating a harmonious outdoors.

Home in Lynchburg

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.

4.94 out of 5 average rating, 117 reviews

Cabin in Bryant

Hoot Owl Cabin – Private Hot Tub & Outdoor Living

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.

Two kayaks in vibrant orange and blue are positioned on a concrete patio, adjacent to a green lawn. Trees with budding leaves and flowering branches frame the serene lakeside view. A covered deck above provides shade, enhancing the inviting outdoor space.

4.95 out of 5 average rating, 37 reviews

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

4.98 out of 5 average rating, 207 reviews

The image captures a serene outdoor scene featuring a poolside gazebo and an inviting swimming pool. Lush greenery surrounds the area, while a vibrant sunset paints the sky in warm hues, enhancing the tranquil atmosphere.

Guest suite in Trenton

Family Fun! Private Pool, Hot Tub, Fire Pit

"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

A modern two-story cottage showcases a blend of blue siding and stone accents. Large windows provide natural light, while the spacious driveway leads to a double garage. A well-maintained lawn features organized landscaping with small shrubs and a concrete pathway to the entrance.

4.98 out of 5 average rating, 60 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!

A contemporary two-story home showcases a light-colored exterior with a gabled roof and a covered front porch. A balcony extends from the upper level, complemented by a ceiling fan. The landscaped area features low shrubbery and a paved pathway leading to the entrance.

5 out of 5 average rating, 37 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.

A private salt-water pool is surrounded by a spacious patio. Several lounge chairs offer comfortable seating options, complemented by red umbrellas providing shade. A barbecue grill is visible nearby, and a low white fence encircles the area, with a backdrop of residential buildings and a clear sky.

4.92 out of 5 average rating, 24 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

The exterior view showcases a Craftsman-style house bordered by a spacious deck. A wooden pergola arches over part of the deck, enhancing the outdoor living space. The yard features manicured grass and is enclosed by a black fence for added privacy.

4.93 out of 5 average rating, 135 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.

A modern house with a striking dark exterior stands against a colorful sunset. The façade features large windows framed by light trim, with a prominent gabled entrance. The surrounding yard is well-maintained, and a glimpse of the lake is visible in the background.

4.94 out of 5 average rating, 64 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.

Popular amenities for Winchester rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

The entryway features a welcoming porch with two comfortable seating areas, one composed of wooden rocking chairs and another wicker chair. A decorative welcome mat greets guests, while a handcrafted wreath adorns the door, inviting all into the cozy interior beyond.

4.73 out of 5 average rating, 22 reviews

Lakeside Luxe | Lake + Pool Access

A front porch is featured with two stylish chairs, framed by a well-maintained stone and siding exterior. Sunlight highlights the inviting entrance, while neatly trimmed shrubs provide a touch of greenery. The porch steps lead to the main door, enhancing accessibility.

4.97 out of 5 average rating, 103 reviews

Latitude Adjustment - Lake Cottage

5 out of 5 average rating, 15 reviews

A wooden dock extends over the calm lake, with two Adirondack chairs positioned for lakeside relaxation. Kayaks in various colors are visible at the front, surrounded by lush greenery and trees that frame the serene water.

Home in Monteagle

Lakefront, 3 Boats + Pizza Oven, Gorgeous!

4.97 out of 5 average rating, 29 reviews

An infinity pool is visible on a wooden deck, offering expansive views of lush greenery and rolling hills under a colorful sky. The scene evokes a sense of serenity with trees surrounding the area, complementing the natural landscape.

Home in Trenton

Firefly Mountain- Newly Remodeled

An open living space features two patterned armchairs positioned across from a spacious sofa. The area is well-lit by multiple ceiling fans and recessed lighting. Large windows provide ample natural light and scenic views, while a dining area with high-backed stools is visible in the background.

5 out of 5 average rating, 11 reviews

The Old Fashioned w/ lake view & FREE pontoon!

A bright sunroom with panoramic lake views features large windows allowing natural light to fill the space. A comfortable white sofa is accompanied by two rattan chairs, creating a relaxing atmosphere. A ceiling fan maintains airflow, and light wood flooring enhances the openness.

4.97 out of 5 average rating, 72 reviews

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

4.98 out of 5 average rating, 49 reviews

Home in Trenton

Pool, Spa, 2 Kitchens, 5 Baths, 15m to Chatt!

4.87 out of 5 average rating, 46 reviews

A charming home with a light-colored exterior is set amidst lush greenery. A spacious deck with seating options faces a stone patio surrounded by vibrant foliage, creating an inviting outdoor area. Large windows provide ample natural light, enhancing the connection to the surrounding nature.

Home in Sewanee

Forest Retreat: Poolside Bliss Close to Campus

Other vacation rentals with a pool

A warm and inviting bedroom features a queen size bed with a neatly arranged quilt and decorative pillows. A stained glass window adds color, while two doors lead to the outside. A bedside lamp and a basket placed on the bed complete the cozy setting.

Cottage in Tullahoma

4.81 out of 5 average rating, 26 reviews

The Acorn at 12 Oaks Vacation Rental.

A charming brick home features a front porch with several steps leading up to the entrance. A decorative fountain is positioned in a landscaped area with neatly trimmed shrubs and flower beds, highlighting the welcoming atmosphere of the property.

Home in Estill Springs

Paradise of Love

4-bedroom Lake house in Twin Creeks Winchester TN

An open living area features large glass doors that offer views of the surrounding woods. A wooden dining table sits beside a comfortable sofa, while colorful rugs add a touch of vibrancy. Natural light fills the space, enhancing the connection to the outdoor landscape.

Cabin in Monteagle

Atypical Cabin in Clifftops near Sewanee

A row of colorful floating cabins reflects on calm water, captured under a cloudy sky. A white mug rests on a railing at the forefront, adding a touch of warmth to the serene view of the cabins and surrounding landscape.

Cabin in Guild

Floating Cabin 3 BR

Cabin in Monteagle

New place to stay

Comfortable forest vacation home near Sewanee

Home in Tullahoma

Villa in the middle of the Forest near waterfalls

A modern kitchen features light green cabinetry and a large white island with three wooden stools. Pendant lights hang above the island, illuminating the space. Stainless steel appliances, including a refrigerator and oven, are visible, along with open shelving displaying decorative items.