House vacation rentals in Winchester

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Top-rated house rentals in Winchester

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Top guest favorite
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
4.93 out of 5 average rating, 126 reviews

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.

Guest favorite
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
4.89 out of 5 average rating, 468 reviews

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.

Top guest favorite
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
4.93 out of 5 average rating, 192 reviews

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.

Top guest favorite
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.
Home in Monteagle
4.98 out of 5 average rating, 110 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.

Top guest favorite
Home in Tracy City
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!

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.

Guest favorite
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.
Home in Tracy City
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.

Guest favorite
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.
Home in Winchester
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.

Top guest favorite
A modern structure features a sleek black exterior with wooden shutters. A covered porch is highlighted by two chairs and a potted plant, inviting relaxation. Lush greenery surrounds the home, providing a serene outdoor environment.
Home in Winchester
5 out of 5 average rating, 34 reviews

The Hangout on Heath Lane

Enjoy a peaceful experience at this centrally-located home. The Hangout is half a mile from the beautiful Twin Creeks Marina and 1 mile to historic downtown Winchester! Other local attractions include: -Grab a coffee and enjoy a tasty breakfast or lunch at Walnut Hill Coffee Shop -For a delicious, upscale dinner, be sure to visit Filo's Tavern -Head out for a tour and tasting at Jack Daniels Distillery -Grab some tickets to the Cavern's for a memorable concert experience.

Top guest favorite
Home in Decherd
4.99 out of 5 average rating, 119 reviews

"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.

Guest favorite
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.
Home in Winchester
4.93 out of 5 average rating, 133 reviews

Lovely Lake View Home at Twin Creeks Marina

This Craftsman-style, lake-view house is located in the private, gated lakeside community of Twin Creeks Village at scenic Tim's Ford Lake in Winchester, TN. It features an open floor plan with 4 bedrooms, 3 baths, game room, screened porch and huge deck overlooking the lake. Use the included golf cart to go to the swimming pools, marina, bar & grill or on-site convenience store. Information on boat & jet ski rentals are available at the marina shop.

Guest favorite
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
4.92 out of 5 average rating, 123 reviews

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.

Popular amenities for Winchester house rentals

When is the best time to visit Winchester?

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Quick stats about house rentals in Winchester

  • Total vacation rentals

    Explore 90 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at ﺩ.ﺇ331 per night before taxes and fees

  • Verified guest reviews

    Over 2,770 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Winchester vacation rentals include wi-fi access

  • 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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