Vacation rentals in Cowan

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!

Meadow View Retreat

Enjoy your stay at Meadow View Retreat with a beautiful view of the farm from the peaceful, serene back yard. We have a 72 acre farm and a family business located walking distance from the airbnb where you can grab a coffee, a bite to eat + stroll around the greenhouses! This 2 BDR house is the perfect stay for families, couples getaway or business trips. Conveniently located in Winchester, a short drive to the beautiful historic downtown Winchester, Tim’s ford Lake and Sewanee University.

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

Whitetail Creek Lodge Close to Campus

Escape to Sewanee this spring at a private 34-acre mountain retreat just minutes from campus. Surrounded by peaceful forest scenery, this redesigned home offers expansive covered patios, a private pond dock, and inviting outdoor spaces perfect for relaxing in the fresh mountain air. Gather around the outdoor fireplace after days spent exploring campus events and nearby trails. With spacious accommodations and comfortable amenities throughout, this retreat is ideal for seasonal getaways.

The apARTment/ historic railroad inn, pet-friendly

Open liv/din/kitchen w/wood floors sequestered in Franklin House historic railroad boutique hotel. Private ensuite Q. BR & bath w/ walk-in shower. LR has convertible couch/full size bed. Enter via back parking lot. Charming lobby, banquet room. In house Cafe. Walk to restaurants, shops, Vintage Texaco & Cowan Railroad Museum! The railroad town of Cowan is the real small town America deal! Near Winchester, Sewanee/U. of the South. the Caverns, Jack Daniels. Hiking, biking & boating.

Modern Monteagle A-frame with Hot Tub

Welcome to Camp Mae, a Scandinavian inspired A-Frame stay in Monteagle, TN. Minimalist designed yet elegant, offering the perfect escape- minutes from the Fiery Gizzard hiking trail and Monteagle. Relax in the hot tub or gather around the fire pit. For eco-conscious travelers, we provide an electric car charger. Experience seclusion of the mountains while only minutes from world class hiking, local restaurants and shops. This retreat harmonizes luxury with nature in a serene setting.

Long Weekend

Tranquility and beauty surround this home located on campus and close to The Cross. Long Weekend can comfortably house 10 people. The main floor has one bedroom and bathroom, a full eat -in kitchen with new dishwasher, a cozy den with fireplace, a dining room, two porches, and a garage. Upstairs are 3 more bedrooms and two full baths. Enjoy hiking, cooking, Sewanee events, or just gazing out the windows over the pond. We hope you enjoy our family home as much as we do.

"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.

Waterfront Access | Lake Views | Dock | Pool Table

Indulge yourself with private waterfront access and stunning million dollar views in this sunny slice of paradise. Experience our waterfront lounge, on-site boat dock, outdoor fireplace, pool table, mini golf putting green, tiki lamps, luxurious jacuzzi tub with spa jets, outdoor dining, sleepy sunroom, charcoal grill, 4K smart TV's, and fully inspired gourmet chef's kitchen. Welcome to "Lakeside Paradise."

Nanny’s House

Located in a country setting on a quiet road, this fully renovated 1800+ sq ft house comes with a 1 acre yard, screened-in porch, and patio with view of the mountains. Local attractions include The Caverns (9.3 miles), South Cumberland State Park (13 miles), Tim’s Ford Lake (15 miles), Old Stone Fort State Park (20 miles). Located halfway between Nashville and Chattanooga about 2 miles from I-24, exit 127.

Cabin 111 - the best in location and comfort!

Cabin 111 has a queen bed, wifi, roku tv, small refrigerator, microwave, coffee maker, and full bath. A deck off the back gives additional space for relaxing. SUPER close to the campus of the University of the South and downtown Sewanee. Enjoy privacy while having access to most things within a short walk. Hiking trails, restaurants, campus! Or just enjoy the nature and deer from the side patio.

Secluded Bluff Cabin, Stargazing Hot Tub & Firepit

A private, adults-only escape with jaw-dropping bluff views, a starlit hot tub, and cozy firepit—designed for romance, reconnection, and rest. Watch the sunrise with coffee on the covered patio, toast s’mores under the stars, or hike to hidden waterfalls just minutes away. Quail Ridge Retreat is a luxury hideaway for couples craving serenity, seclusion, and unforgettable views. No pets.