Vacation rentals with a pool in Winchester

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.

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.

Gorgeous Lakefront! Marina, Fire Pit, Location!

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.

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

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

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!

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.

Monteagle/Sewanee forest cottage with amenities

Connect with nature in our new, bright and modern 2 bedroom/1 bath guest house tucked away in the forest, but in a gated community with community lake with beach, pool, playground, tennis, pickleball and basketball courts. Watch deer from the screened porch, stroll 1/2 mile to the serene lake, or drive 15 minutes to hike the vast trail systems of the University of the South or South Cumberland State Park. Then return to rest and stream movies over high-speed fiber internet.

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.

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.

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.

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!