Holiday rentals with a pool in Winchester

5 out of 5 average rating, 94 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

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.

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, 52 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

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.

4.81 out of 5 average rating, 26 reviews

Dry Jack Tim-Hot Tub, Water Views, Marina

This beautiful Lake home is located in the pristine community of Twin Creeks, has water views, steps from the pool, hot tub on back patio. 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.

4.9 out of 5 average rating, 147 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.

4.95 out of 5 average rating, 65 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. Nearby: Fiery Gizzard, Head of the Crow, & Salvage Gulf State Parks w/ trailheads, waterfalls, hiking, biking (Mountain Goat Tr), Sewanee-University of the South, Monteagle, Tracy City, the Caverns-Pelham, Big Foot Adventure, Tim's Ford Lake, & Chattanooga.

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.

4.96 out of 5 average rating, 105 reviews

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. Use the golf cart at your leisure, two kayaks for paddling on the lake. 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.

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.

5 out of 5 average rating, 20 reviews

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.

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, 39 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.

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.

4.85 out of 5 average rating, 34 reviews

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

Custom designer home built by Legacy Lake Homes on Tim’s Ford Lake! Located in the gated community of Twin Creeks. Steps to the Marina and restaurant, this is a lake front home. Beautiful lake view from 3 bedrooms with upper and lower back decks. Plenty of space for 2 or more families/ multiple couples. Beautiful neighborhood pool, fire pit, and cute little putt-putt golf area. Golf cart (six seater) included with signed waiver.

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.

4.89 out of 5 average rating, 35 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 contemporary white house with a stylish facade features a covered entrance. A golf cart is parked on the driveway, adjacent to a well-maintained lawn. Two large windows flank the door, contributing to the home's inviting appearance.

5 out of 5 average rating, 17 reviews

Lake House in Winchester, Tn w/Golf Cart

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!

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, 76 reviews

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

4.88 out of 5 average rating, 48 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

4.9 out of 5 average rating, 21 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

5 out of 5 average rating, 17 reviews

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

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 of Love

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, 130 reviews

Sunset Ridge cabin 21 miles from Chatt, TN! Indoor

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.

4.94 out of 5 average rating, 145 reviews

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

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