Family-friendly holiday rentals in Winchester

Private Dock - Best Cabin Tims Ford Lake

Great cabin located directly on Tims Ford Lake. Cabin has been updated and includes nice, well stocked kitchen as well as a deck (with grill). Enjoy our dock - fish, swim and use our two kayaks, paddle board and a canoe. Plenty of space to tie your boat up to our dock in a mostly private cove. Please read the guest access section for more details on lake access. Close to some great attractions - Jack Daniels Distillery (19 mi), Bonnaroo (25 mi), Univ. of the South (19 mi), Winchester (5 mi)

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

Tiny House

You will feel right at home in this adorable Tiny Home with RV Hookups! This picture-perfect little cottage has a bedroom with queen size bed, full bath with tile walk-in shower, full kitchen with all of the amenities, and living room with queen size sleeper sofa. The back porch offers peace, quiet, and spectacular mountain views. This property is super convenient to Tims Ford Lake, The Caverns music venue, Jack Daniels Distillery, University of the South, and historic downtown Winchester.

The Hangout on Heath Lane

Welcome to The Hangout on Heath Lane! Just 1/2 mile from Twin Creeks Marina and 1 mile from historic downtown Winchester, our new 2-bedroom retreat is the perfect home base for lake weekends, concerts at The Caverns, Jack Daniel's tours, and family getaways. Enjoy modern comforts, sparkling cleanliness, and the small-town charm that keeps guest coming back! We also suggest: -Coffee & breakfast or lunch at Walnut Hill Coffee Shop -For a delicious, upscale dinner, go visit Filo's Tavern

Beautiful Tims Ford lakefront home

Beautiful 3 level lake front home right by the water with no steps to the dock. Plenty of room for large groups of people and great for families with kids. Five bedrooms with a bonus room that has plenty of extra beds. Located less than a mile from public boat ramp. Located in quiet cul-de-sac, on a cove with no wake next to the main channel. If there are any dates that are blocked off that you want please message us because we may have some blocked off dates that we can open up for you.

Sunset Cottage +Dock on Tims Ford Sleeps 12

Welcome to Sunset Cottage, a spacious and serene lakeside escape nestled in the heart of Winchester. Located less than a mile from the town square, this charming cottage offers both the tranquility of lakefront living and the convenience of nearby dining and shopping. Relax as you take in breathtaking sunset views from the back covered porch. With a private boat dock, you can easily set out for a day on the water. Designed for comfort and relaxation, Sunset Cottage is the ideal getaway.

Meadow View Retreat

Enjoy your stay at Meadow View Retreat with a beautiful view of the farm. We have a 72 acre farm and a family business located walking distance from the airbnb. We are a 10 minute drive to Tim’s Ford Lake, Twin Creeks Marina & historic downtown Winchester + 15 minutes from University of the South. This 2 bedroom guesthouse is the perfect stay for you and your loved ones. Enjoy the private, quiet back porch with a view of the pond and the farm. Beautiful sunrise + sunset views too!

Lake Home, Dock, Theatre, Hot Tub, FirePit, Kayaks

Take it easy at this unique and tranquil getaway. This beautiful lake home is one of it's kind at Tim's Ford. The house is nestled in a quiet rural neighborhood with woods in the backyard. The dock is only a small golf cart ride away. Enjoy beautiful lake views at your own private dock! This house is equipped with an amazing home theatre system, game room, hot tub, fire pit, kayaks and plenty more amenities! Tim's Ford Dam is only one mile away and has a public boat launch for you :)

Dock on Lake! Walk to Downtown Shops/Rest/Movies!

Charming, *Pet Friendly* well-loved 1950s lake house on Tim’s Ford Lake. Walking distance to grocery and downtown movie theatre, boutiques, restaurants and library. Near Twin Creeks marina/restaurant where you can rent boats. While here, you can swim at the dock; play darts, checkers or fuse ball; go out on the lake; walk to the Oldham Theatre; go hiking in Tim’s Ford State Park or nearby Sewanee; go to the Tullahoma drive-in theatre; or visit nearby Jack Daniel’s distillery.

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.

Clean Lines and Simple Comfort

This 2 bed, 2 bath apartment duplex is located just two miles from Tims Ford Lake. Whether you’re in town for a weekend or an extended stay, this space offers everything you need for a relaxing and comfortable visit. Each room features a comfortable queen bed, fresh linens and ample closet space. The kitchen is stocked with cookware, stainless steel appliances, and a coffee maker for your morning brew. Book your stay and enjoy an experience that’s clean with a blend of style.

Water's Edge - Lakeside retreat

Experience spring by the water at this beautiful lakefront retreat designed for relaxing family getaways and group stays. The home features a private dock, spacious outdoor entertaining areas, panoramic lake views, and a hot tub perfect for unwinding after days spent outdoors. Gather around the outdoor gas fire pit in the evenings or enjoy meals together in the spacious dining areas inside. A peaceful and comfortable home base for enjoying the beauty of the season.

Outdoor spaces