
Cabin vacation 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.

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.

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.

Cozy Cabin with River Access
Rustic bliss at this 3BR/2BA log house on the Elk River—only 5 min from downtown & 15 min from Jack Daniel's Distillery! Modern perks for ultimate comfort: high-speed WiFi, 50" HDTV w/ streaming, stocked kitchen, washer/dryer, AC, heat, grill, crackling fire pit w/ firewood, hammock by the waterfall, kayaks, and complimentary gourmet coffee. Pet-friendly paradise! Sleeps 8: 1king, 2queens, sofa. Effortless self check-in; free parking. Your serene riverfront adventure awaits!

The Coalmont Cabin - Romantic Lakefront Escape
A quiet lakeside retreat made for slow mornings and star-filled nights. Wake to coffee on the deck as the fog drifts across the water, geese gather along the shoreline, and the world feels still for just a little longer. Spend your afternoons out on the lake, gliding through lily pads in a moment that feels like a scene from The Notebook. Tucked among the trees with a saltwater spa beneath the stars, The Cabin is where peaceful seclusion meets unforgettable memories.

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.

CABIN w/ AMAZING VIEWS, HOT TUB, FIRE PIT
Welcome to Monteagle Cabin! Relax, unwind and enjoy the view! Monteagle Cabin has three bedrooms and loft all featuring queen beds, two full bathrooms, kitchen with seating for 10, a fire pit, large deck, a hot tub, and best of all- amazing views! 10 Minutes to South Cumberland State Park 14 Minutes to The University of the South 20 Minutes to The Caverns 30 Minutes to Sweetens Cove Golf Club 50 Minutes to Chattanooga 90 Minutes to Nashville

Fire Lake Lodge Volleyball, Hot Tub, Kayaks!
PRIVACY, FUN, and HI SPEED INTERNET await for all at the newly finished Fire Lake Lodge at beautiful Normandy lake. You can Walk to the beach/lake access area from the cabin, but why walk when you have your very own golf cart and kayaks! Hot tub, Beach Volleyball court, pool table, 6’ fire pit, outdoor shower and more! Everything is PRIVATE, nothing is shared on this almost two acre property located right above the boat ramp at fire lake.

The Sundowner
Come find serenity at The Sundowner where the view drops layers of stress, the sunsets connect you with wonder, and the deer, coyotes, owls, and other denizens reconnect you to nature. The kitchen is well stocked. Fiber internet. Grill, firepit, washer/dryer. 20 min to The Caverns & Fiery Gizzard Trl w Foster Falls; 15 min to Perimeter Trl, Sewanee; 5 to Monteagle. 3bd/2ba includes open master in loft. Toxin free.
Popular amenities for Winchester cabin rentals
Cabin rentals with a hot tub

Elk Ridge Cabin – Private Hot Tub & Stunning Views

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

Terralodge: Wild Luxury on Monteagle Mountain

Luxurious Lakefront Cabin w/ Hot Tub & Fire Pit

Cozy Bluff View Cabin w/ Hot tub in Monteagle

Tennessee Riverfront Cottage w/HOT TUB on 3 acres

Treetop Retreat - Amazing Views, Hot Tub, Secluded

Window Rock | Jackson Point · Modern Bluff Retreat
Pet-friendly cabin rentals

Fireside Cabin on the Bluff

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

Tanasi River Cabin

The Overlook Cabin: Breath-taking Views & King Bed

Kingfisher Cabin-a PMI Scenic City rental

Secluded Country Cabin between city and country

Tadpole Cabin at Creek Road Farm

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

Hundred Oaks

Luxe 2BR Cabin C by MHM Luxury Properties

Lillypad Cove at The Retreat at Water's Edge

Proctor's Haven - Private Pond & Bluff View

White Deer Lodge | Private Cabin on 2 Acres

Reel Simple Lakefront Cabin

Quilters Haven Cabin

The Happy Camper Cabin at Camp Swann
Quick stats about cabin rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at $111 CAD 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
- Point Park
- South Cumberland State Park
- Chattanooga Zoo
- Creative Discovery Museum
- Old Stone Fort State Archaeological Park
- Raccoon Mountain Caverns & Campground
- Lowe Mill Arts And Entertainment
- Von Braun Center, North Hall
- Cathedral Caverns State Park
- Short Mountain Distillery
- Huntsville Botanical Garden
- U.S. Space & Rocket Center
- Cumberland Caverns
- Burritt on the Mountain
- Discovery Center
- Chattanooga Whiskey Experimental Distillery
- Tennessee River Park





