Holiday rentals with a pool in Winchester

5 out of 5 average rating, 78 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.

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, 43 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

4.89 out of 5 average rating, 128 reviews

Elk Ridge Cabin – Private Hot Tub & Stunning Views

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

4.78 out of 5 average rating, 18 reviews

Home in Chattanooga

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.

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, 36 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, 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.

4.98 out of 5 average rating, 86 reviews

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

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.

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.

The exterior of a two-story house is presented, featuring a light-colored façade with dark shutters. A covered porch invites guests, while a driveway accommodates a parked golf cart, enhancing accessibility. Lush green grass frames the entrance, reflecting a welcoming atmosphere.

5 out of 5 average rating, 47 reviews

Lakeside Retreat Marina/Pool, Golf Cart, Game Room

Discover luxury living at your lakeside retreat in the prestigious Twin Creeks Marina subdivision on Tims Ford Lake. This exquisite home features indoor and outdoor fireplaces, a game area with foosball and arcade, plus a 6-seater golf cart for exploring. Just minutes away, enjoy a pool and the convenience of Twin Creeks Marina's amenities, including a restaurant, boat rentals, snacks, and gas. Your ultimate vacation experience awaits!

4.93 out of 5 average rating, 110 reviews

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

SUNDAY check in ALLOWED. TRI-STATE CORNER CABIN is located inside Paradise Pointe, 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. Cabin has fireplace, fire pit, hot tub etc. Premises has sand volleyball. Enjoy VIEW from BLUFF & POOL DECKS! Cabin sits behind but between 2 other cabins.

4.98 out of 5 average rating, 41 reviews

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

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 amazing mountain and river vistas, our cabin sits atop easily-accessible Jasper Mountain in East Tennessee. Be ready for miles of hiking trails, restaurants, pools, pickleball courts, playground and more!

Popular amenities for Winchester rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.88 out of 5 average rating, 34 reviews

Luxury 3BR lakeside escape

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.

4.91 out of 5 average rating, 23 reviews

TC Easy Breeezee

Superhost

The exterior of the two-story home is showcased, featuring a covered entryway and a pull-through driveway. Lush greenery surrounds the property, with flower beds adding a touch of color. Strings of lights are visible, enhancing the inviting appearance of the home.

Home in Village of Pelham

4.79 out of 5 average rating, 42 reviews

Private Hot Tub & Pool & backroad to caverns

5 out of 5 average rating, 12 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!

4.87 out of 5 average rating, 38 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

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

4.85 out of 5 average rating, 13 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 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 de Amor

A spacious living area features a warm wooden ceiling and a stone fireplace. Seating includes a large leather sofa and an armchair, with a coffee table in the center. A flat-screen television is mounted on the wall, while large windows allow for natural light and views.

4.93 out of 5 average rating, 136 reviews

Mountain High Cabin with hot tub, fire pit, & indo

4-bedroom Lake house in tranquil Winchester

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