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Vacation rentals with a pool in Winchester

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Quick stats about vacation rentals with a pool in Winchester

  • Total vacation rentals

    Explore 40 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at €78 per night before taxes and fees

  • Verified guest reviews

    Over 1,400 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Winchester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winchester rentals

  • 4.9 Average rating

    Winchester stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated rentals with a pool in Winchester

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
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

Private Treehouse Retreat! Sauna|Hot Tub|Pool

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.

5.0 out of 5 average rating, 106 reviews
Top guest favorite
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.
Home in Winchester

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

4.98 out of 5 average rating, 62 reviews
Guest favorite
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.
Home in Winchester

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

4.92 out of 5 average rating, 48 reviews
Top guest favorite
The cabin is situated amidst lush greenery, featuring a sturdy wooden deck supported by stone pillars. Large windows are framed by natural wood, allowing sunlight to illuminate the rustic facade while the surrounding trees enhance the tranquil atmosphere.
Cabin in Tullahoma

Private lakefront log cabin w/dock & hot tub

Be one with nature at this unique, tranquil getaway on Tim’s Ford Lake. Enjoy the two fireplaces in a “rustic” meets “modern” log cabin on 10 acres of privacy that is adjoined to over 2000 acres of park land. There is 450 ft of lake front & private dock to store your boat/toys, but the dock is not usable Nov 1 to April 1. Enjoy nature walks, spend lake time with friends or just relax taking in the amazingly beautiful views, hot tub and amenities. This truly is our happy place.

4.93 out of 5 average rating, 131 reviews
Top guest favorite
The exterior of a modern custom home is displayed, featuring a combination of white and blue siding. A spacious green lawn surrounds the property, while a circular seating area with chairs is positioned in front of the home, inviting outdoor relaxation.
Home in Winchester

Barefoot Dreams

Barefoot Dreams is a newer custom lake home vacation rental in the gated community of Barefoot Bay on Tims Ford Lake in Winchester TN. This luxury lake house rental is perfect for families and groups seeking a Tims Ford Lake cabin, waterfront getaway, or Tennessee lake vacation home. Enjoy stunning water views, modern design, and an open-concept layout. Ideal for boating, fishing, swimming, and lakefront relaxation. A peaceful yet fun-filled family vacation rental on the lake.

5.0 out of 5 average rating, 26 reviews
Top guest favorite
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.
Home in Winchester

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.

5.0 out of 5 average rating, 49 reviews
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.
Home in Winchester

Lakeside Luxe | Lake + Pool Access

Lakeside 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, community kayak launch and firepit, and a private fenced backyard with a cozy outdoor fireplace. Only a two minute walk to the community lake access and pool and just one mile from charming downtown Winchester, you'll be minutes from great dining, shopping, and entertainment.

4.79 out of 5 average rating, 28 reviews
Top guest favorite
Home in Winchester

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.

4.94 out of 5 average rating, 72 reviews
Guest favorite
A modern house exterior is depicted, featuring a gable roof and a mix of vertical and horizontal siding. Black window frames and decorative wood accents provide contrast against the light-colored façade. A paved driveway leads to a single-car garage, with a white vehicle parked nearby.
Home in Winchester

Luxury 3BR lakeside escape

Discover serenity at New Latitude in Twin Creeks Village! Nestled near the picturesque shores of Tim’s Ford Lake, our 3-bedroom, 3-bathroom retreat offers a haven for relaxation and rejuvenation. Enjoy the scenic charm of Twin Creeks Village, where tranquility meets luxury just moments from Twin Creeks Marina. Indulge in lakeside living at New Latitude. Book your getaway now and experience the beauty and calm of Tim’s Ford Lake!

4.88 out of 5 average rating, 43 reviews
Top guest favorite
Home in Winchester

Latitude Adjustment - Lake Cottage

Enjoy the lake with all the amenities you could dream of! At Twin Creeks resort & Marina offers three resort style pools, marina, restaurant all golf cart accessible, designer decorated home with all the comforts of home. Enjoy sunsets on the lake, fires at the firepit, grilling on the patio, hiking around the resort. Family friendly with fold-a-away crib, toys, books and other things to entertain children.

4.96 out of 5 average rating, 111 reviews
Superhost
The expansive property features a multi-level home with large windows showcasing the lakeview. A spacious deck houses seating areas, while a well-maintained inground pool glistens nearby, surrounded by lush greenery and outdoor spaces for relaxation.
Home in Winchester

Paradise Resort-Dock, Pool, Hot Tub, Movie Theatre

Escape to luxury at your expansive 10,000 sq. ft. lakeview home, where every detail has been designed to create an unforgettable experience. Perfect for family reunions, large gatherings, or a lavish getaway with friends, our resort-style property comfortably sleeps 20 guests and offers a plethora of amenities that allow you to have your own private resort stay on 14 private acres.

4.97 out of 5 average rating, 39 reviews
Top guest favorite
Home in Winchester

Tennessee Pearl: lakefront-amazing views-lake toys

Welcome to The Tennessee Pearl, a newly constructed 4 bedroom, 3.5 bath two-story home, with breathaking views, that sits directly lakefront on Tims Ford Lake. Restaurants and shopping are 1 mile away in historic downtown Winchester, TN. Twin Creeks Marina with restaurant and boat rental is just minutes away.

5.0 out of 5 average rating, 26 reviews

Popular amenities for Winchester rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favorite
The living area features a large sectional sofa in a soft blue hue, arranged around a dark wooden coffee table. A stone fireplace stands against a white-painted wall, with a television mounted above it. Windows provide views of the surrounding lake, allowing natural light to brighten the space.
Home in Winchester

EASY PEASY on Tim's Ford Lake, golf cart, pool

4.88 out of 5 average rating, 41 reviews
Guest favorite
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, Moore County

Private indoor pool & sauna

4.9 out of 5 average rating, 31 reviews
Guest favorite
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

4.88 out of 5 average rating, 58 reviews
Top guest favorite
A clear blue pool is framed by colorful lounge chairs, inviting relaxation under the sun. The house in the background features a prominent gabled roof and a wide covered porch, enhancing outdoor enjoyment. Lush greenery surrounds the property, providing a serene environment.
Home in Shelbyville

Secluded Luxury Farm Home, TN Whiskey Trail nearby

5.0 out of 5 average rating, 27 reviews
Top guest favorite
Home in Winchester

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

4.98 out of 5 average rating, 84 reviews
Guest favorite
Home in Winchester

4-bedroom Lake house in Twin Creeks Winchester TN

5.0 out of 5 average rating, 6 reviews
Guest favorite
Home in Winchester

By the pool

4.85 out of 5 average rating, 13 reviews
Guest favorite
The exterior of a modern two-story house is presented, featuring light gray siding and a white panel accent. A neatly landscaped front yard includes shrubs and a concrete walkway leading to the entrance. Bright blue skies and scattered clouds create a serene backdrop.
Home in Winchester

Barefoot Bungalow Bright airy lakeside home

4.89 out of 5 average rating, 28 reviews

Other vacation rentals with a pool

Top guest favorite
A charming cabin exterior is highlighted, featuring a teal facade and red rocking chairs on the porch. Inside, a spacious bed is seen with neatly arranged white linens and decorative pillows. A sweeping view of the landscape reveals a community pool area next to recreational spaces under a clear sky.
Cabin in Jasper

Luxurious Cabin in Jasper Highlands - Blackberry

4.98 out of 5 average rating, 55 reviews
Top guest favorite
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

Spacious Home in “Tiny Home” Lake Community

4.96 out of 5 average rating, 69 reviews
Superhost
Cabin in Jasper

Chic 2BR Cabin D by MHM Luxury Properties

4.84 out of 5 average rating, 76 reviews
Top guest favorite
A modern living area features large windows that allow ample natural light and provide views of the surrounding forest. A comfortable sofa is positioned beside a light wooden coffee table, and a two-tone shelving unit adds a functional accent to the space.
Cottage in Monteagle

Monteagle/Sewanee forest cottage with amenities

5.0 out of 5 average rating, 87 reviews
Top guest favorite
The exterior of a cabin is shown, featuring double French doors framed in wood and surrounded by a snowy landscape. A wooden deck with lattice detailing provides access, while tall trees stand in the background, lightly dusted with snow.
Cabin in Monteagle

Hundred Oaks

4.98 out of 5 average rating, 93 reviews
Top guest favorite
The exterior of a modern white house is shown, surrounded by neatly maintained grass and landscaping. A paved driveway leads to the entrance. The structure's design features a mix of angled roofs and large windows, while a golf cart is parked nearby.
Home in Winchester

The Curlin House, Lakeside Getaway Tim’s Ford Lake

5.0 out of 5 average rating, 13 reviews
Guest favorite
Vacation home in Winchester

Lakeside Laurel | HOT TUB • Firepit • Walk to Town

4.97 out of 5 average rating, 39 reviewsA spacious bedroom features a large bed with two decorative pillows set against a soft blue wall. A bedside table with a lamp is positioned beside the bed, while a modern chandelier hangs from the ceiling, providing ambient lighting.
Home in Winchester

Spacious Family Gem: Golf Cart - 2 Ensuites - Pool

4.89 out of 5 average rating, 18 reviews

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price€155€148€167€174€224€264€260€211€188€172€163€155
Avg. temp5°C8°C12°C17°C21°C25°C27°C27°C23°C17°C11°C7°C

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