
Cabin holiday rentals in Winchester
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Top-rated cabin rentals in Winchester
Guests agree: these cabins are highly rated for location, cleanliness and more.

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)

Waterfall Log Cabin
Cozy Log Cabin just feet away from the top of our 2 magnificent private waterfalls. The Falls at Sewanee Creek is located in America’s most biodiverse area on Tennessee's Eco-Rich Cumberland Plateau. Walk to the observation bench at the top of the biggest 50 ft waterfall. Follow the trail behind the falls. Adventure awaits on a rugged, bouldering hike, past cascades and the second big waterfall to two private caves. Disclaimer: Flow of all Waterfalls is subject to weather fluctuations.

The Overlook Cabin: Breath-taking Views & King Bed
Looking for the perfect getaway that is peaceful, beautiful, and not amongst other vacation homes? Look no further! The Overlook Cabin is completely private and super cozy. It's also one of the most scenic spots in Tennessee! From the front porch you can enjoy a panoramic view of the Sequatchie Valley while watching the sunset as it lights up the evening sky. Our cabin includes a super comfy king bed, firepit, grill, and many more amenities. Book today and make memories that last forever!

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.

Sunrise Mountain Cabin
Welcome to Sunrise Mt. Cabin is located on top of the Cumberland Plateau with a great view of the valley check out our 2 other cabins Patriot's Retreat & Sunrise Mtn Treeshouse. The cabin has approximately 1400 square feet and is fully furnished with full kitchen and more. Hiking trails and fishing pond only a short walk away. Several major state parks with hikes within a few miles of the cabin. The cabin has fiber optic WiFi which is not shared. Pet cats not allowed; we are allergic.

The Calming Cabin — Where Peace Settles In
Relaxing, Park-Like Setting | Convenient to Trails, Waterfalls, and THE CAVERNS • Comfortable, Full-Size Log Home • Front Porch Swing • Fire-pit, Picnic Table & Gas Grill • Coalmont OHV Park & Rock Climbing Close By • Convenient Amenities • 1GB Internet/WiFi • Full Kitchen, Ready to Cook • Loft Space w/Cozy Queen Futon • Spacious Yard • 7 min. Drive From Interstate • 15 min. from The Caverns & Sewanee Uni • Private Parking; Room for RV/Hauler • Small-Town Friendliness & Dining Close By

Red Room Cabin ~ "The Fortress" Adult playhouse!
Red Room Cabins TM is the first adult themed vacation. It's a sensual place to get away and escape everyday life. Explore new things with the "Red Room" experience. Come relax in the private hot tub, have a drink in front of the fireplace, and let your imagination run wild in this unique, one of a kind lifestyle retreat. This is a two bedroom with two King size beds. A make up vanity for the ladies! Plenty of fun & games! You will see why it is so popular! Travel insurance recommended!

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.

Cozy Cabin on Tims Ford Lake
Come stay at a hand built log cabin nestled right on Tims Ford Lake. Enjoy a cup of coffee and watch birds fly in a rocking chair on the front porch. Relax in the porch swing as you see fish jump from the water. Grill out on the back porch while watching the sun set. There is a dock available for fishing. The cabin is five miles from Tims Ford State Park, eight miles from Jack Daniels Distillery and downtown Lynchburg, eleven miles from Tullahoma, and fifteen miles from Winchester.

The Coalmont Cabin - Romantic Lakefront Escape
The Coalmont is a 4 acre waterfront retreat on top of the South Cumberland Mountains of Tennessee, between Nashville and Chattanooga. This 460 sq ft "tiny" cabin sleeps up to 4. Amenities abound with boats, hot tub, fishing, zip line, lawn games, large decks for gathering, fire pit, and beautiful scenery. Perfect retreat for couples looking for a romantic getaway, families wanting to unplug and reconnect with quality time, or anyone looking for a quiet place to work remotely.

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.

Secluded Country Cabin between city and country
Our Secluded Country Cabin is located just off I-59 and only one exit from the I-24 split near Trenton, GA. We’re conveniently located only 15 minutes from downtown Chattanooga, Cloudland Canyon State Park and Lake Nickajack! You will enjoy the peaceful country atmosphere of this private oasis while surrounded by nature, fresh air, and beauty. You will love the convenience if you’re traveling through, and there’s lots to do if you plan to stay a while.
Popular amenities for cabin rentals in Winchester
Cabin rentals with a hot tub

Hot tub, game room, fire pit and amazing view!

Cozy 2 bed Cabin. Hot Tub. Fire Pit. 15 min DT

Terralodge: Wild Luxury on Monteagle Mountain

Heaven’s View Lodge, Pool, Pet Friendly

Spectacular Mountain Top Cabin Getaway

Restful Haven - Hot Tub at Secluded Modern Cabin |

Cozy Bluff View Cabin w/ Hot tub in Monteagle

Tennessee Riverfront Cottage w/HOT TUB on 3 acres
Pet-friendly cabin rentals

Tanasi River Cabin

The Palm Springs Cabin at Camp Swann

Proctor's Haven - Private Pond & Bluff View

Kingfisher Cabin-a PMI Scenic City rental

Secluded cabin in the woods by a lake

*Hot Tub *Fire Pit *Near The Caverns & Hiking!

Reel Simple Lakefront Cabin

Family+Pet-Friendly Lake Cabin•Quiet Nature Views
Private cabin rentals

Country Escape By the Caverns

Cozy Mountain Cabin w/ Creek, near Dining & Hiking

Secluded Log Cabin Near Waterfalls - Sauna, WiFi

Luxurious Lakefront Cabin w/ Hot Tub & Fire Pit

VACATION CABIN - Sunday Morning Rentals

Quilters Haven Cabin

Scenic View of Sequatchie Valley

Rising Sun Retreat-Sewanee Cabin
Quick stats about cabin rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $102 SGD per night before taxes and fees

Verified guest reviews
Over 260 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winchester rentals

4.9 Average rating
Winchester stays are highly rated by guests – averaging 4.9 out of 5!
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- Cloudland Canyon State Park
- Tennessee Aquarium
- Monte Sano State Park
- Coolidge Park
- Chattanooga Choo Choo
- Rock City
- Hunter Museum of American Art
- Creative Discovery Museum
- South Cumberland State Park
- Raccoon Mountain Caverns & Campground
- Dublin Park
- Point Park
- Chattanooga Zoo
- U.S. Space & Rocket Center
- Burritt on the Mountain
- Cathedral Caverns State Park
- Cumberland Caverns
- Chattanooga Whiskey Experimental Distillery
- Huntsville Botanical Garden
- Old Stone Fort State Archaeological Park
- Finley Stadium
- Discovery Center
- Short Mountain Distillery
- Lowe Mill Arts And Entertainment




