Vacation rentals with a pool in Winchester

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Winchester

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

%{current} / %{total}1 / 1
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
5 out of 5 average rating, 71 reviews

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.

Guest favorite
A modern two-story home features clean lines and a light-colored exterior. Large windows are present on the upper level, complemented by a stylish black garage door. Minimal landscaping includes a small tree near the front entrance, and a paved driveway offers access to the home.
Home in Winchester
4.94 out of 5 average rating, 16 reviews

Dry Jack Tim- Water Views, Pool, Outdoor Fireplace

This beautiful Lake home is located in the pristine community of Twin Creeks, has water views, steps from the pool, and 3 min to the marina. Bring your own boat to launch at the marina private dock. No boat? no problem! The Marina offers the following rentals: pontoon boats, kayaks and paddle boards. The on-site store will take care of all of your boating needs including gas, beverages, sunscreen, snacks etc… Drafts and Watercrafts bar and grill frequently features live music on the weekends.

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
5 out of 5 average rating, 43 reviews

Lakefront Haven–Fall Escape w/ Firepits + Kayak

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

Guest favorite
Cabin in Bryant
4.94 out of 5 average rating, 107 reviews

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.

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
4.94 out of 5 average rating, 34 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

Top guest favorite
Home in Chattanooga
5 out of 5 average rating, 8 reviews

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.

Top guest favorite
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
4.98 out of 5 average rating, 174 reviews

Fall Vibes- Spa & Fire Place | Mins to Chattanooga

"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

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
5 out of 5 average rating, 34 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.

Guest favorite
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.
Home in Winchester
4.93 out of 5 average rating, 133 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.

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
4.99 out of 5 average rating, 83 reviews

Hundred Oaks

Clifftops cabin close to the front gate. Nearby lake, bluff view, waterfalls, hiking. Sewanee University 3-4 miles away. Chattanooga-30-45 min, Nashville-90 min. Important: the stairs leading to the loft are very steep so it’s probably not the best option for young children or the elderly. We do not allow for any pets on the property. During the winter months from Christmas to March, the washer/dryer will be unavailable due to freezing weather.

Guest favorite
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.
Home in Winchester
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.

Guest favorite
Cabin in Bryant
4.91 out of 5 average rating, 218 reviews

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

SUNDAY check in ALLOWED. BIG TIME HILL CABIN is located inside Paradise Pointe is gated & on a mountain at tristate corner of AL/TN/GA. Walk our HIKING TRAIL to tristate corner & be in 3 states at once. Paradise Pointe has 1 HuGe INDOOR POOL HOUSE with outdoor deck. 19 rentals has access to pool house. Cabin has hot tub, WIFI, fireplace, charcoal grill & fire pit!

Popular amenities for Winchester rentals with a pool

Quick stats about vacation rentals with a pool in Winchester

  • Total rentals

    40 properties

  • Nightly prices starting at

    € 94 before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace