
Cabin holiday rentals in Winchester
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Winchester holiday rentals start at $116 SGD per night before taxes and fees

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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!
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)

The Sundowner
Get into the rhythm of relaxation. This is a place where stress falls away, the sunsets connect you with wonder, and the deer, coyotes, owls reconnect you to nature. In the woods with views of ridges from large covered porch. Toxin free. Well stocked kitchen. High speed internet w 2 smart TVs. Washer/dryer, fire pit, charcoal grill. Great night sky. 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.

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.

Holliday Hide Away
1200 sq. ft. very rustic converted pole barn. The floors are stained concrete and the walls are rough saw mill hewn poplar boards. Located on 3 acres of beautiful well kept property. It does not border the lake but is surrounded by Tims Ford Lake and less than 5 minute drive to 3 boat docks and launches. Close to restaurants, shopping venues, hiking trails, water falls and golfing. Pool table, cornhole set, board games & cards in cabin. Visit historic Franklin County and surrounding areas.

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 Bluff View Cabin w/ Hot tub in Monteagle
Welcome to "In The Pines", a charming bluff-view cabin nestled in the heart of Monteagle, TN! Whether you're seeking a peaceful retreat, catching a show at The Caverns, or exploring the scenic trails of South Cumberland State Park, this is the perfect getaway. Relax and unwind with family and friends in this cozy mountain escape, featuring 3 bedrooms, 2 full bathrooms, and a loft with a full-size fold-out futon. Enjoy breathtaking bluff views from the patio or soak in the jacuzzi!

Private lakefront log cabin w/dock & hot tub
Be one with nature at this unique, tranquil getaway on Tim’s Ford Lake. Enjoy the two fireplaces in a “rustic” meets “modern” log cabin on 10 acres of privacy that is adjoined to over 2000 acres of park land. There is 450 ft of lake front & private dock to store your boat/toys, but the dock is not usable Nov 1 to April 1. Enjoy nature walks, spend lake time with friends or just relax taking in the amazingly beautiful views, hot tub and amenities. This truly is our happy place.

VACATION CABIN - Sunday Morning Rentals
We are in Winchester, TN, and are located within a SHORT 5 MINUTE WALKING DISTANCE to Tims Ford Lake and Devil Step Boat Launch. Sunday Mornings Rentals is a completely equipped cabin that ensures a relaxing getaway. Perfect for all of your boating, fishing, and hiking recreations. The charming town square is approximately 5 miles from the rental - offering unique shops, a quaint theatre, and restaurants that are sure to provide enjoyment for everyone. PETS NOT ALLOWED.

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.
Popular amenities for cabin rentals in Winchester
Cabin rentals with a hot tub

Terralodge: Wild Luxury on Monteagle Mountain

Restful Haven - Hot Tub at Secluded Modern Cabin |

Luxurious Lakefront Cabin w/ Hot Tub & Fire Pit

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

Cozy Cabin with Mountain Views!

Battle Cry Cabin

The Getaway at The Retreat, Monteagle

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

Fireside Cabin on the Bluff

Proctor's Haven - Private Pond & Bluff View

The Palm Springs Cabin at Camp Swann

Whispering Falls Remote Hideaway

Bubbe's Barn at Camp Chet

Secluded cabin in the woods by a lake

Reel Simple Lakefront Cabin

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

Spacious Home in “Tiny Home” Lake Community

Wildflower, Lakefront Cabin w/EV Charger

Calming Cabin—Stay for Rest, Relaxation & Area Fun

Cozy Cabin

Nordic Spruce Cabin | The Caverns, Hiking, Trails

COUNTRY HAVEN TINY CABIN - 7 MIN WALK TO CAVERNS!

Cabin at Normandy Lake

The Cabins At Rivers Edge
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- Rentals with a firepit Winchester
- Rentals with lake access Winchester
- Rentals with a kayak Winchester
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- Pet-friendly rentals Winchester
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- Rentals with pools Winchester
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- Cloudland Canyon State Park
- Tennessee Aquarium
- Monte Sano State Park
- Rock City
- Chattanooga Choo Choo
- Coolidge Park
- South Cumberland State Park
- Point Park
- Hunter Museum of American Art
- Von Braun Center, North Hall
- Raccoon Mountain Caverns & Campground
- Chattanooga Zoo
- Old Stone Fort State Archaeological Park
- Creative Discovery Museum
- U.S. Space & Rocket Center
- Huntsville Botanical Garden
- Cumberland Caverns
- Cathedral Caverns State Park
- Lowe Mill Arts And Entertainment
- Short Mountain Distillery
- Burritt on the Mountain
- Discovery Center
- Chattanooga Whiskey Experimental Distillery
- Barfield Crescent Park





