Holiday rentals with a patio in Winchester

The Mockingbird MADE SOUTH Cottage @ Water's Edge

The Mockingbird (a MADE SOUTH Cottage) welcomes you to the Water's Edge community in Tracy City, TN, just down the road from Monteagle and Sewanee. This area boasts tons of hiking and nature while also offering great restaurants and unique shopping. Hike down to Deer Lick Falls, a private 80 foot waterfall that guests have access to about 10 minutes down the road, or explore the gorgeous campus of The University of the South. Epic golf can be found at Sweetens Cove and The Course at Sewanee.

Wartrace Depot: Hot Tub, Pool Table, Games & Charm

Welcome to Wartrace Depot Retreat, an inviting escape in historic Wartrace. Built in the year 1900, this recently remodeled gem seamlessly blends vintage charm with modern comfort. Enjoy the pool table, hot tub, and fun games! Located 1 hour from Nashville, 15 min from I-24, and a short drive from Bell Buckle, Manchester, and Shelbyville. Explore the shops of Wartrace on foot! Your stay promises a unique fusion of history and indulgence. Book now for a timeless experience! Heart = Discount!

Highpoint Hideaway A | Lakefront Home | WatersEdge

Set upon one of the largest waterfront lots in the community, this tiny home offers a unique experience that's perfect for couples, friends, or family. You'll be enchanted by the tranquility of the lake as it stretches out before you, providing a serene backdrop to your stay. The heart of this property is its outdoor living spaces (2 large decks, complete with outdoor seating and a grill) as evening falls, gather around the fire pit to roast marshmallows, share stories, and make memories.

Sweet Dee's Tiny Home

FEATURES A HOT TUB! Relax in style at Sweet Dee's (formerly listed as The Alexander), a luxury tiny home in the Retreat at Deer Lick Falls. Serene, tranquil, rustic, wooded setting with relaxation stations throughout the community. The Retreat at Deer Lick Falls is a gated luxury tiny home community in southeast Tennessee. The community is only 15 minutes from the University of the South in Sewanee. Guests of the Retreat also have access to Retreat at Waters Edge and it's lake.

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.

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

Twin Pines - Large Porch w/ Fireplace, Hot Tub

NEW! Come relax & unwind at this beautiful property. Each space has been thoughtfully designed for your comfort with luxurious styling. Enjoy an open layout w/ vaulted ceilings, rustic - but modern - features, a large screened in porch as part of a 1000 sqft deck, and multiple outdoor amenities - hot tub, fireplace, secluded fire pit, and grill. Designer furniture styling throughout - no stone has been left unturned with the setup of this property.

Spacious Lakeside Oasis for All Occasions

Escape to a serene lakeside getaway on 30 private acres of woods, trails, and stunning views. This fully updated and spacious home is perfect for romantic escapes, small group retreats, or family gatherings. Enjoy unmatched privacy and tranquility while being just a short drive from The University of the South. Whether you’re hiking, relaxing, or reconnecting with loved ones, this peaceful haven is ready to welcome you.

Private upstairs studio with quiet deck.

Keep it simple at this peaceful and centrally-located space.Has microwave and coffee maker and medium size refrigerator. There is a small dining table. The bath has a full tub and shower. Private entrance with concrete driveway and accommodating parking. Secure environment. There are stairs leading up to the space. The front window gets morning sun and the rear deck is mostly shaded.