Holiday rentals with a pool in Winchester

4.86 out of 5 average rating, 42 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

Discover a charming winter sanctuary in Sewanee. This beautifull 3-bedroom, 2-bath home is the ideal base for a peaceful getaway or university visit. With the campus and vibrant local scene just a short walk away, convenience meets tranquility. This warm escape from the frosty air is complemented by serene, private outdoor areas. Located near some of the area's best dining options, you can explore or just relax in comfort. This inviting home is a perfect blend of style, location, and serenity!

5 out of 5 average rating, 85 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.

Superhost

A serene view of a meandering lake is surrounded by lush greenery and wooded banks. The water reflects the blue sky and scattered white clouds, creating a calm and peaceful landscape. The vibrant colors of nature are prominently displayed in this tranquil setting.

5 out of 5 average rating, 15 reviews

Beautiful New Construction Lakefront!

Escape to comfort and style in this brand-new home nestled in a serene, gated community on the shores of beautiful Tims Ford Lake. Take in breathtaking lake views, or stroll to the water’s edge for a day of lakeside fun. Minutes to fine dining. Exclusive guest access to the private community clubhouse featuring a spacious saltwater pool with stunning lake vistas. Located near Tims Ford Marina with easy access to daily boat and kayak rentals. In house boat and kayaks also available for rent.

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, 45 reviews

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

Superhost

4.83 out of 5 average rating, 112 reviews

Eagles Nest Cabin – Bluff Views & Hot Tub!

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

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, 58 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.

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.

4.93 out of 5 average rating, 61 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.

4.95 out of 5 average rating, 37 reviews

A cozy bedroom is highlighted with a black metal bed frame featuring soft, neutral bedding. The exterior of the cabin reveals a welcoming entrance with red chairs on the porch, overlooking manicured lawns and a pool area with tennis courts to the side.

Cabin in Jasper

Pools+Pickleball+Hiking+Campfires+Sweetens Cove

Welcome to the mountaintop of Jasper Highlands! Less than 30 minutes to downtown Chattanooga, our single level cabin will be the perfect location for a serene weekend retreat. Located in the gated community with incredible mountain and river vistas, our cabin sits atop easily-accessible Jasper Mountain in East Tennessee. Be ready for miles of hiking trails, restaurants, pool, pickleball courts, playground and more!

4.9 out of 5 average rating, 224 reviews

Big Time Hill Cabin with an indoor pool, hot tub,

Big Time Hill 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!

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 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

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, 99 reviews

Latitude Adjustment - Lake Cottage

5 out of 5 average rating, 14 reviews

A warm and inviting living area is highlighted by a stone fireplace, crackling with fire. Two plush armchairs and a spacious sectional sofa surround a textured coffee table. A festive Christmas tree adds a holiday touch, while large windows allow natural light to fill the space.

Home in Monteagle

Lakefront, 3 Fireplaces + Pizza Oven, Gorgeous!

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 @ Twin Creeks Resort w/ Pool!

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!

A gated entrance is presented, featuring sturdy metal gates flanked by stone pillars. A clear sky is visible above, with several houses lining the street beyond the gates. Lush greenery is situated near the entrance, providing a serene atmosphere.

4.88 out of 5 average rating, 8 reviews

Lake House Dreams

4.88 out of 5 average rating, 17 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

Other holiday rentals with a pool

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 de Amor

4.93 out of 5 average rating, 113 reviews

Tri-state Corner Cabin with a fire pit, hot tub, &

4.96 out of 5 average rating, 182 reviews

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

The cabin's open living area showcases a combination of natural wood and stone elements. A cozy seating arrangement is positioned around a wall-mounted TV, with a fireplace below. A dining space with multiple chairs is visible, while decorative greenery adds an inviting touch to the ceiling.

4.89 out of 5 average rating, 128 reviews

Sunset Ridge cabin 21 miles from Chatt, TN! Indoor

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

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

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.