Holiday rentals with a pool in Winchester

5 out of 5 average rating, 10 reviews

Home in Monteagle

Lakefront, 3 Fireplaces + Pizza Oven, Gorgeous!

Escape to Camp McGu, a beautiful log home with a magical lakefront setting in Monteagle's Clifftops, minutes from world-class hiking, the University of the South, South Cumberland State Park, Fall Creek Falls, and The Caverns. Situated on five private acres, the home has 3 fireplaces, a fire pit and plenty of wood for cozy nights. There are multiple outdoor seating areas and three boats - two hybrid stand-up paddle boards and kayaks and one peddle boat. The renovated kitchen will delight cooks.

4.95 out of 5 average rating, 60 reviews

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 & a pool(coming soon). Nearby: South Cumberland State Park w/ trailheads, waterfalls, hiking, biking (Mountain Goat Tr), Sewanee-University of the South (many trails), Monteagle, Tracy City, the Caverns-Pelham, Big Foot Adventure, Tim's Ford Lake, & Chattanooga.

5 out of 5 average rating, 41 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 • Spa Getaway • Fantastic community pool for the hot summer days • Screened in, heated porch with TV and sound system • Kayak, Paddleboard 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

5 out of 5 average rating, 14 reviews

The Lakefront Getaway! Pool, Fire Pit, Marina!

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.

5 out of 5 average rating, 5 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.

4.98 out of 5 average rating, 172 reviews

Guest suite in Trenton

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

4.98 out of 5 average rating, 49 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!

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.

4.93 out of 5 average rating, 131 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.

4.99 out of 5 average rating, 82 reviews

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.

4.93 out of 5 average rating, 60 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.