House vacation rentals in Winchester

4.93 out of 5 average rating, 126 reviews

A cozy bedroom features a spacious bed with soft, patterned bedding. Above the bed, a framed artwork adds a touch of color. A closet with neatly arranged shelves and a blue dresser is visible, providing ample storage. Soft lighting enhances the room's atmosphere.

Home in Sewanee

Relax & Unwind in Cozy Farm Stay 7 mins from I-24

Come enjoy a cozy getaway in Sewanee! You’ll love this space because of the location, amenities, and cleanliness. This home is best suited for couples, small families and those traveling with pets. This mobile home has an open layout. It’s 700 square feet and sits near the woods, off a back road, bordering a horse pasture and trees. It has a spacious fenced-in yard. Located 7 minutes off I-24 for those driving thru, and a short walk or drive from Mountain Goat Trail if you want to walk or jog.

4.9 out of 5 average rating, 467 reviews

A rustic log cabin is set within a spacious green yard, surrounded by trees. A gravel path leads to the entrance, with stairs ascending to the front porch. Windows provide views of the natural landscape, reflecting a serene outdoor environment.

Home in South Pittsburg

Martin Springs Cabin.

This country cabin is a great base for exploring the nearby South Cumberland Park and surrounding area. Convenient to Sweetons Cove Gulf, The Caverns, Adventure Offroad Park, Sewanee, Monteagle, South Pittsburg/Cornbread Festival, Jasper Highlands. right next to I-24. You can't see any other homes from the cabin and adjacent meadow. Year round creek in the property. Meadow trail. New Hot Tub and all new Tuft & Needle mattresses for 2022! Basic amenities provided. Includes Wi-Fi and DVD player.

4.93 out of 5 average rating, 192 reviews

The exterior of the property features a unique sloped roof with a combination of stone and wood materials. Surrounded by greenery, the entrance is approached via a paved path that leads to a welcoming entrance area. Outdoor seating is visible on the balcony, nestled among the trees.

Home in Manchester

Chalet 638 - state park, golf & The Caverns

Short walk to a state park with golfing. This first floor living space has a kitchen, walk-in closet, large wood fireplace, workout equipment, washer/dryer, grill, fire pit and lots of space. Old Stone Fort Archeological Park with multiple hiking trails, fishing, canoeing and a $9 a round golf course are seconds away. Close to I-24 this centrally located Tennessee property gives equal access from Nashville to Chattanooga. Explore parks, vineyards, distilleries and Tennessee history from here.

The spacious living area features large glass windows that showcase woodland views and allow natural light to fill the space. A mix of modern and cozy furnishings includes a black sofa, orange leather chairs, and a wooden dining table, creating an inviting atmosphere.

4.98 out of 5 average rating, 109 reviews

Stayframe: designer getaway w/ private lake access

Welcome to our custom-built Aframe in the woods just 90 minutes from Nashville. This quiet retreat perched on the Cumberland Plateau gives you access to the hikes and waterfalls the area is known for, while offering an elevated guest experience. Enjoy the soaking tub, gas fireplace, fast wifi, Smart TV, well-appointed kitchen, and bluff views. Sewanee University, Cumberland Caverns, Fiery Gizzard, and Sweetens Cove are all within a short drive. Sorry, no parties, events, or photoshoots.

4.99 out of 5 average rating, 100 reviews

Little Green Cottage

Relax & unwind where mother nature meets modern nature at the Little Green Cottage. Each space is thoughtfully designed for a comfortable & luxurious stay. Enjoy an open layout w/ vaulted ceilings & natural earth-tone features, a full functioning kitchen & dining area, bedrooms w/ king size beds that each come with their own attached bathroom & a large screen porch w/ a view that will take your breath away. All the fun, recreational activities are right outside your door! Dog friendly!

An outdoor seating area features blue and white lounge chairs arranged around a central fire pit. The shaded porch swing offers a serene view of the lake, framed by lush greenery. The dock and numerous boats can be seen in the background.

4.96 out of 5 average rating, 122 reviews

Private dock/gazebo on quiet cove. Tims Ford Lake!

Indulge in the tranquility of Tims Ford Lake, TN! Our exquisite 5-star cottage, just 6 miles from Tims Ford State Park/Marina, beckons you to unwind. Conveniently situated 18 miles from Tullahoma and 8 miles from Winchester, our boat-friendly haven features a private dock and a circular drive. Minimum rental age: 25. Ensure a seamless stay by signing our legal Rental Agreement and presenting a government-issued ID. Book now for a worry-free lakeside escape – your perfect retreat awaits!

Superhost

Home in Manchester

4.9 out of 5 average rating, 407 reviews

Fire Lake Estate-*Views *Hot Tub* *GAME ROOM* WiFi

All fresh, new and ready for guests, this completely renovated lake home with gorgeous water and sunset views will amaze you and leave you breathless as you watch the famous Fire Lake sunset from almost every room in the house. Located conveniently just minutes off interstate I-24, centered 1 hr from Nashville and 1 hr from Chattanooga and Only 8 miles from Bonnaroo Music festival. Bring your boat or kayak as the small neighborhood is located right next to a boat ramp and swimming area.

A modern cabin is shown with a sleek design, featuring a covered porch with a rail and stone base. Large windows allow natural light to enter, surrounded by trees in autumn colors. A grassy area is visible in the foreground.

4.97 out of 5 average rating, 117 reviews

Cozy Two Bedroom Cabin with Hot Tub in Waters Edge

New 2 bedroom cabin in the Water's Edge community. Spacious family room to enjoy fireplace, TV, and dining area. Private hot tub! Master bedroom has a king sized bed. The second bedroom has 2 twin bunk beds, trundle, and a loft. Outdoor living space patio with a grill, table, couch, and firepit. Multi video game system. There is a community lake, playground, and hiking trail. We have two stand-up paddle boards, 1 adult kayak, and 1 child kayak. Pack n' play and high chair available.

A serene outdoor space features four red Adirondack chairs arranged around a circular stone fire pit. The scene is illuminated by the warm glow of the setting sun, casting soft light through the surrounding trees and reflecting on the tranquil lake in the background.

4.89 out of 5 average rating, 123 reviews

Dock on Lake! Walk to Downtown Shops/Rest/Movies!

Charming, *Pet Friendly* well-loved 1950s lake house on Tim’s Ford Lake. Walking distance to grocery and downtown movie theatre, boutiques, restaurants and library. Near Twin Creeks marina/restaurant where you can rent boats. While here, you can swim at the dock; play darts, checkers or fuse ball; go out on the lake; walk to the Oldham Theatre; go hiking in Tim’s Ford State Park or nearby Sewanee; go to the Tullahoma drive-in theatre; or visit nearby Jack Daniel’s distillery.

4.99 out of 5 average rating, 118 reviews

Home in Decherd

"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/ YouTube TV and streaming tv. Only 3.5 miles off 1-24 exit 127, Pelham, Winchester.

4.92 out of 5 average rating, 121 reviews

A charming cottage built with light-colored stone is framed by lush green shrubs and blooming hydrangeas. The entrance features a covered archway, with windows on either side allowing natural light to enter. A well-maintained pathway leads to the front door.

Home in Lynchburg

Mulberry Cottage Guest House

Mulberry Cottage Guest House was built in the late 1800's. It is nestled under shade trees and surrounded by hydrangeas in the front. The cottage is located behind the library at the only traffic light in historic Lynchburg, home of the oldest registered distillery in the United States and the cottage is within walking distance, so what are you waiting for? Come visit the Jack Daniel Distillery and enjoy our home.

A modern tiny home interior showcases an open living area with a comfortable sofa and a decorative rug. A wall-mounted television, stylish pendant light, and stainless steel kitchen appliances are visible, while a unique artwork enhances the space. A wooden staircase leads to an upper loft area.

4.98 out of 5 average rating, 214 reviews

The FOX Tiny Home @ The Retreat at Water's Edge

Welcome to The FOX, our beloved tiny home nestled in the woods of beautiful Tracy City, TN. After nearly two years, we've finally completed building our dream home, and we are excited to share it with you. Inside the home you'll find many of Kelly's custom creations that were designed to make the space totally unique. We hope you experience a peaceful, relaxing vacation when staying at our home.

Popular amenities for Winchester house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The exterior of a modern two-story home is displayed, featuring a light-colored facade with black accents. A garage door complements the structure, while a decorative blue door offers an inviting entrance. The manicured lawn extends towards the serene lake visible in the background.

5 out of 5 average rating, 43 reviews

Lakefront Haven–Fall Escape w/ Firepits + Kayak

An open living space features two patterned armchairs positioned across from a spacious sofa. The area is well-lit by multiple ceiling fans and recessed lighting. Large windows provide ample natural light and scenic views, while a dining area with high-backed stools is visible in the background.

5 out of 5 average rating, 11 reviews

The Old Fashioned @ Twin Creeks Resort w/ Pool!

The exterior of a two-story house is presented, featuring a light-colored façade with dark shutters. A covered porch invites guests, while a driveway accommodates a parked golf cart, enhancing accessibility. Lush green grass frames the entrance, reflecting a welcoming atmosphere.

5 out of 5 average rating, 45 reviews

Lakeside Retreat Marina/Pool, Golf Cart, Game Room

5 out of 5 average rating, 10 reviews

Stunning Lakefront! Pool, Kayaks, Bikes, Marina!

A modern house with a striking dark exterior stands against a colorful sunset. The façade features large windows framed by light trim, with a prominent gabled entrance. The surrounding yard is well-maintained, and a glimpse of the lake is visible in the background.

4.93 out of 5 average rating, 61 reviews

Basecamp Retreat TimsFordLake

4.86 out of 5 average rating, 36 reviews

A charming home with a light-colored exterior is set amidst lush greenery. A spacious deck with seating options faces a stone patio surrounded by vibrant foliage, creating an inviting outdoor area. Large windows provide ample natural light, enhancing the connection to the surrounding nature.

Home in Sewanee

Forest Retreat: Poolside Bliss Close to Campus

A contemporary two-story home showcases a light-colored exterior with a gabled roof and a covered front porch. A balcony extends from the upper level, complemented by a ceiling fan. The landscaped area features low shrubbery and a paved pathway leading to the entrance.

5 out of 5 average rating, 35 reviews

The Modern Mainstay at Barefoot Bay

The exterior view showcases a Craftsman-style house bordered by a spacious deck. A wooden pergola arches over part of the deck, enhancing the outdoor living space. The yard features manicured grass and is enclosed by a black fence for added privacy.

4.93 out of 5 average rating, 133 reviews

Lovely Lake View Home at Twin Creeks Marina

Weekly house rentals

5 out of 5 average rating, 28 reviews

A serene view of a house positioned beside a still pond, surrounded by tall, bare trees. The wooden structure features a sloping roof and large covered porches. The reflection of the house and trees in the water creates a peaceful scene, showcasing the natural setting.

Home in Sewanee

Whitetail Creek Lodge Close to Campus

5 out of 5 average rating, 16 reviews

The exterior of the property features a traditional single-story home with a welcoming porch and a spacious front yard. A covered carport is adjacent to the house, providing shelter. Lush green trees frame the scenic view, enhancing the overall appeal of the property.

Home in Estill Springs

Timberhill Home-Walk to the Lake!

5 out of 5 average rating, 95 reviews

The exterior of a renovated house is shown, featuring a light blue facade with black shutters. Lush green grass surrounds the pathway leading to the entrance. A screened-in porch is visible on one side, and flowering bushes add a touch of color to the landscape.

Home in Hillsboro

Nanny’s House

A spacious living area is highlighted by floor-to-ceiling glass walls, providing breathtaking mountain views. A modern linear fireplace is situated beneath a mounted television, while a light-colored sofa with decorative pillows faces the outdoor deck. The open layout connects to a dining area visible in the background.

5 out of 5 average rating, 28 reviews

"A Modern Vue"-Luxury-Hot Tub-Arcade

A modern cabin exterior is framed by lush greenery, with a spacious porch featuring large glass windows. Adirondack chairs surround a stone fire pit, creating a cozy gathering area for outdoor enjoyment.

5 out of 5 average rating, 8 reviews

Chic Monteagle Cabin | Scenic Views & Serene Vibes

A cozy interior of a tiny home features an open layout with a comfortable seating area and a light-colored sofa. A wooden coffee table is centered in front of the sofa. In the background, a kitchen area showcases modern appliances and cabinetry. Natural light filters in through several windows.

4.91 out of 5 average rating, 43 reviews

The Little Lodge Retreat

5 out of 5 average rating, 74 reviews

A handcrafted cedar wood cabin is set against a lush green backdrop. A wooden deck surrounds the front, equipped with steps leading to the entryway. An American flag is displayed near the porch, while a stone chimney adds rustic charm to the exterior.

Home in Lynchburg

Cedar Cabin of Lynchburg - 3 miles to Jack Daniels

The entrance features a wooden door with multiple glass panels, complemented by a dark brown welcome mat and a tall, rustic sign that reads 'WELCOME.' The porch is framed by vertical siding and surrounded by greenery.

4.96 out of 5 average rating, 28 reviews

A quiet getaway.

Private house rentals

The exterior of a modern house is presented, featuring dark siding and a sloped roof. A smooth driveway leads to a single garage, while a welcoming front porch with seating overlooks a manicured lawn. Surrounding trees provide a natural backdrop.

5 out of 5 average rating, 20 reviews

Kayak Kove* DOCK* Lakefront*NEW

4.98 out of 5 average rating, 61 reviews

Chic Lake Retreat - Cabin by Lake

5 out of 5 average rating, 25 reviews

A modern home exterior is displayed, featuring a welcoming façade with a combination of black and white siding. Three garage doors are positioned symmetrically, framed by neatly landscaped trees and shrubs. A spacious driveway leads up to the entrance, surrounded by open green space.

Home in Estill Springs

Our Sweet Little Piece of Tennessee

A private hot tub is illuminated with soothing blue light, situated on a wooden deck surrounded by trees. Soft string lights are draped overhead, enhancing the serene atmosphere at night.

5 out of 5 average rating, 48 reviews

Mountain Mist - HOT TUB & King bed w/ fire pit

4.95 out of 5 average rating, 19 reviews

A green A-frame cabin is surrounded by trees, featuring a welcoming front porch with two chairs. A stone pathway leads to the entrance, and an American flag is displayed proudly nearby. The outdoor area showcases well-maintained grass and landscaping, enhancing the cabin's natural setting.

Home in Tullahoma

A-Frame on Tims Ford Lake Private Boat Dock w/slip

The kitchen features modern stainless steel appliances, including an oven and microwave, set against green cabinets. A spacious granite countertop with a farmhouse sink is complemented by decorative floating shelves displaying dishware and plants, while a patterned backsplash adds visual interest.

4.95 out of 5 average rating, 37 reviews

1940's Cottage Near Square/Lake

5 out of 5 average rating, 30 reviews

A serene outdoor area is displayed with a fire pit surrounded by four wooden chairs. Lush green grass and trees provide shade, while the water of Tims Ford Lake glimmers in the background. A private dock is visible, enhancing the lakefront experience.

Home in Estill Springs

Just a short path to the lake! Private dock!

A firepit area is surrounded by Adirondack chairs, arranged in a circular formation on a flat surface near the calm waters of the lake. Lush greenery and trees frame the peaceful setting, with the serene water reflecting the surrounding nature.