House holiday rentals in Winchester

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Top-rated house rentals in Winchester

Guests agree: These houses are highly rated for location, cleanliness and more.

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Top Guest favourite
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
4.92 out of 5 average rating, 132 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 favourite
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, 474 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 favourite
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
4.94 out of 5 average rating, 209 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.

Guest favourite
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.
Home in Winchester
4.96 out of 5 average rating, 123 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!

Guest favourite
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, 125 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 favourite
A wooden dock extends over the tranquil water, featuring kayaks and paddleboards secured alongside. An upper deck with several chairs offers a relaxing space, while views of the lush surroundings create a calming atmosphere. The water sparkles under clear blue skies.
Home in Winchester
4.98 out of 5 average rating, 101 reviews

Lake Home, Dock, Theatre, Hot Tub, FirePit, Kayaks

Take it easy at this unique and tranquil getaway. This beautiful lake home is one of it's kind at Tim's Ford. The house is nestled in a quiet rural neighborhood with woods in the backyard. The dock is only a small golf cart ride away. Enjoy beautiful lake views at your own private dock! This house is equipped with an amazing home theatre system, game room, hot tub, fire pit, kayaks and plenty more amenities! Tim's Ford Dam is only one mile away and has a public boat launch for you :)

Top Guest favourite
A modern two-story house features a green exterior with white trim and a welcoming porch. An American flag hangs from the porch, and soft outdoor lighting illuminates the entrance. A driveway leads to a garage, with trees providing a natural backdrop.
Home in Tullahoma
5 out of 5 average rating, 103 reviews

Lakeside Retreat at The Reserve w/ Golf Cart

Beautiful lakeside home on Tim's Ford Lake! Short Walk or Golf Cart ride to Blue Gill Grill & Holiday Landing Marina. Boat Parking on the Driveway during your stay! First Floor: Master Bed with Full Bath, Dining Room, Living Room, Kitchen (Fully stocked with basic spices and cooking utensils). Outside Patio with Fire Place and seating. Second Floor: BR 2- King Bed. BR 3 Queen Bed, Loft Space, Sectional Couch, Pull out Queen. *No Smoking *Max 10 Guest *Front Door Security Cam*

Guest favourite
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
4.9 out of 5 average rating, 124 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 favourite
Home in Decherd
4.99 out of 5 average rating, 122 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.

Superhost
A charming farmhouse is set against a backdrop of open green space, featuring a covered front porch and large windows that provide natural light. The exterior is highlighted by a green metal roof and white siding, creating a welcoming presence in a serene rural setting.
Home in Winchester
4.82 out of 5 average rating, 136 reviews

Spacious 4BR/3BA Home Near Tims Ford Lake

Welcome to your beautifully renovated 1940s 4-bedroom, 3-bathroom vacation home near Tims Ford Lake! This spacious historic retreat comfortably sleeps 8 and offers everything you need for a relaxing getaway in Winchester, TN. Enjoy fast Wi-Fi, a Roku Smart TV, and a large private yard perfect for watching the sunrise from the back porch and sunset from the front. Large bedrooms, a cozy reading nook, and a spacious kitchen and living area awaits you!

Top Guest favourite
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, 134 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.

Top Guest favourite
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, 132 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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Avg. price$348 NZD$348 NZD$348 NZD$312 NZD$460 NZD$545 NZD$555 NZD$505 NZD$392 NZD$383 NZD$418 NZD$369 NZD
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Quick stats about house rentals in Winchester

  • Total holiday rentals

    Explore 90 holiday rentals in Winchester

  • Nightly prices starting at

    Winchester holiday rentals start at $52 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,920 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Winchester holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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