Holiday rentals in Winchester

Unbeatable Charm & Convenience On The Square!

Escape to The Heritage Lofts, just off of the thriving Winchester square. Only minutes from Tims Ford Lake, this fabulously-renovated apartment has all of the comfort and amenities you need to feel right at home during your stay in Winchester. See the local scene in style with one of our bike or paddle board rentals, and shop til you drop on our thriving downtown square. Then grab a meal before relaxing in the comfortable confines of your spacious loft. There isn't a better spot to stay in town!

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.

Private dock/gazebo on quiet cove. Tims Ford Lake!

Indulge in the tranquility of Tims Ford Lake, TN! Our exquisite 5-star cottage, just 6 miles from Tims Ford State Park/Marina, beckons you to unwind. Conveniently situated 18 miles from Tullahoma and 8 miles from Winchester, our boat-friendly haven features a private dock and a circular drive. Minimum rental age: 25. Ensure a seamless stay by signing our legal Rental Agreement and presenting a government-issued ID. Book now for a worry-free lakeside escape – your perfect retreat awaits!

Lakeside Retreat at The Reserve w/ Golf Cart

Beautiful lakeside home on Tim's Ford Lake! Short Walk or Golf Cart ride to Blue Gill Grill & Holiday Landing Marina. Boat Parking on the Driveway during your stay! First Floor: Master Bed with Full Bath, Dining Room, Living Room, Kitchen (Fully stocked with basic spices and cooking utensils). Outside Patio with Fire Place and seating. Second Floor: BR 2- King Bed. BR 3 Queen Bed, Loft Space, Sectional Couch, Pull out Queen. *No Smoking *Max 10 Guest *Front Door Security Cam*

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 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.

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.

The Hangout on Heath Lane

Enjoy a peaceful experience at this centrally-located home. The Hangout is half a mile from the beautiful Twin Creeks Marina and 1 mile to historic downtown Winchester! Other local attractions include: -Grab a coffee and enjoy a tasty breakfast or lunch at Walnut Hill Coffee Shop -For a delicious, upscale dinner, be sure to visit Filo's Tavern -Head out for a tour and tasting at Jack Daniels Distillery -Grab some tickets to the Cavern's for a memorable concert experience.

Cozy Cabin close to Tims Ford Lake & Jack Daniels

A cozy cabin awaits you located close to Tim's Ford Lake-1/2 mile from Holiday Landing Marina & Blue Gill Restaurant. Lynchburg, home to popular Jack Daniel's Distillery-only 12 miles away; Nashville-90 mins. Made from handcrafted red cedar, you will be met with a woodsy aroma when entering. Special touches can be found throughout including Jacuzzi tub! Truly a unique wooded cottage, equipped to ensure a relaxing getaway. Pet friendly with an additional pet fee.

"Near Caverns and Sewanee 2-bedro/2-bath w/EV char

2 bedroom, 2 full bathrooms, totally remodeled home with a large fenced back yard and fully equipped modern kitchen. Easy drive less than 7-mi to Sewanee, and just 10-miles/ 10-12 min to The Caverns. The "Farm View" house offers country views with privacy. A serene place to relax, unwind and retreat while enjoying pastures and country views. "EV/Tesla wall charger", Starlink internet w/ streaming tv. Only 3.5 miles off 1-24 exit 127, Pelham, Winchester.

Barefoot Bliss w/Stunning Waterfront Lot & Pool

Escape to this beautifully decorated lakeside retreat with stunning water views and flat lot! Enjoy mornings on the covered porch by the fireplace, paddle out on the lake with two provided kayaks, or unwind by the fire pit under the stars. Kids will love the cozy nook with a fun chalkboard wall. Plus, enjoy access to a community pool for extra relaxation. Whether you're seeking adventure or tranquility, this home offers the perfect lake getaway!