Cabin vacation rentals in Winchester

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Quick stats about cabin rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at G$16,740 GYD 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!

Top-rated cabin rentals in Winchester

Guests agree: these cabins are highly rated for location, cleanliness, and more.

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Guest favorite
A comfortable living area is observed, featuring a light-colored sectional sofa and a dark wooden coffee table. Large windows provide natural light, while a rustic dining table and chairs are visible in the background. Decorative wall art and assorted accents highlight the cozy atmosphere.
Cabin in Winchester
4.86 out of 5 average rating, 210 reviews

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)

Top guest favorite
A charming log home is surrounded by lush greenery, featuring a green metal roof and a welcoming front porch with seating. Areas for relaxation are visible, complemented by vibrant flowers along the porch railing, enhancing the natural setting.
Cabin in Tracy City
4.96 out of 5 average rating, 143 reviews

Calming Cabin—Soak Up Peace, Relaxation & Area Fun

Peaceful, Park-Like Setting | Convenient to Trails, Waterfalls, and THE CAVERNS • Comfortable, Full-Size Log Home • Front Porch Swing • Fire-pit, Picnic Table & Gas Grill • Good Weekday Rates for Work Crews • Coalmont OHV Park & Rock Climbing Close By • Convenient Amenities • 1GB Internet/WiFi • Full Kitchen, Ready to Cook • Loft Space w/Cozy Queen Futon • 7 min. Drive From Interstate • 15 min. from The Caverns & Sewanee Uni • Private Parking; Room for RV/Hauler • Friendliness & Dining Close By

Guest favorite
Cabin in Fayetteville
4.85 out of 5 average rating, 185 reviews

Charming Tiny Cabin Minutes from Town

Escape to this modern tiny cabin on scenic Elk River, 5 min from downtown; 15 min from Jack Daniel's Distillery. Perfect for summer river adventures kayaks provided for paddling, fishing, or swimming. Relax by the waterfall or sway in the hammock. Cozy queen bed, high-speed WiFi for work/streaming, window AC, electric heat, indoor plumbing. Grill BBQs on porch, roast s'mores at fire pit. Free gourmet coffee from veteran-owned Montana Coffee Company. Pet-friendly (approval needed), sleeps 2.

Top guest favorite
The exterior of the cabin is shown, featuring a contemporary design with dark grey siding and large windows. A covered porch extends from the front, offering a view of the surrounding landscaping with shrubs and small trees. The tranquil lake is visible in the background.
Cabin in Tracy City
4.95 out of 5 average rating, 112 reviews

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.

Top guest favorite
A charming cabin with a green metal roof is situated on a grassy hillside. Surrounding trees frame the view, while steps lead from the driveway to the entrance. The cabin overlooks the valley, providing a scenic backdrop of rolling hills in the distance.
Cabin in Altamont
4.97 out of 5 average rating, 622 reviews

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.

Top guest favorite
An A-frame cabin is nestled among tall trees, showcasing a modern design with large glass windows. A wooden deck surrounds the entrance, featuring a seating area with chairs and a fire pit. The outdoor area is partially landscaped with natural ground cover.
Cabin in Monteagle
4.96 out of 5 average rating, 160 reviews

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.

Top guest favorite
A view from the porch reveals the serene waters of Tims Ford Lake, bordered by lush greenery. The railing is partially visible, with sunlight filtering through the trees, creating dappled shadows on the deck. A bird feeder hangs nearby, inviting wildlife.
Cabin in Lynchburg
4.96 out of 5 average rating, 227 reviews

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.

Top guest favorite
Cabin in Coalmont
4.98 out of 5 average rating, 374 reviews

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.

Top guest favorite
A spacious living room showcases wood-paneled walls and ceiling. Two comfortable sofas and an armchair are arranged around a wooden coffee table. Decorative pillows add color. Natural light filters through light-filtering shades on the windows, and a large framed photograph is displayed on the wall.
Cabin in Tullahoma
4.94 out of 5 average rating, 210 reviews

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.

Guest favorite
A charming log cabin is surrounded by neatly trimmed hedges and colorful flower beds. The entrance features a set of wooden steps leading to a porch, with sunlight filtering through the lush green trees overhead.
Cabin in Beersheba Springs
4.78 out of 5 average rating, 187 reviews

Tennessee Mountain House

This one bedroom remote cabin is located on the Cumberland Plateau between Monteagle & McMinnville in the National historic district of Beersheba Springs. Three acres of wooded bluff property overlooks Savage Gulf & provides a secluded, quiet getaway. sleeps 4 but suitable for mostly 2 guest. Also, as you will note: this is the guest house which FACES the SIDE of the main house, so please use the main house porch for sitting and enjoying the view as well.

Top guest favorite
A serene lake scene features a boat silhouetted against a vibrant sunset, where rays of light filter through scattered clouds. The calm waters reflect the warm hues of the fading day, with distant tree-covered hills framing the horizon.
Cabin in Manchester
4.89 out of 5 average rating, 250 reviews

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.

Top guest favorite
Cabin in Monteagle
5 out of 5 average rating, 163 reviews

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

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