
House holiday rentals in Winchester
Find and book unique houses on Airbnb
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 $115 SGD per night before taxes and fees

Verified guest reviews
Over 3,030 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
90 of Winchester holiday rentals include wifi 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!
Top-rated house rentals in Winchester
Guests agree: these houses are highly rated for location, cleanliness and more.

Lakefront Haven | Hot Tub | Kayaks, Firepit
Welcome to Lakefront Haven! This home offers a seamless blend of comfort and luxury, providing a retreat for a lakefront getaway. • Lakefront property + beautiful views • Hot Tub • Fantastic community pool for the hot summer days • Screened in, heated porch with TV and sound system • Kayak, 2 Paddleboards and Peleton provided • Deck with gas Weber grill • Backyard firepit with chairs • Well equipped kitchen • Less than two miles from Twin Creeks Marina • Walkable to the downtown Square

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!

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.

Meadow View Retreat
Enjoy your stay at Meadow View Retreat with a beautiful view of the farm. We have a 72 acre farm and a family business located walking distance from the airbnb. We are a 10 minute drive to Tim’s Ford Lake, Twin Creeks Marina & historic downtown Winchester + 15 minutes from University of the South. This 2 bedroom guesthouse is the perfect stay for you and your loved ones. Enjoy the private, quiet back porch with a view of the pond and the farm. Beautiful sunrise + sunset views too!

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 :)

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*

Southern Comfort Lakehouse on Tims Ford Lake
Tims Ford Lake is the best family vacation all year and we have the best view on the lake. We're on Lost Creek with 4 bedrooms, a bunk room, 3 full baths, game room, 2 large decks, a dock with a Hydrohoist and Jet Ski lift. Our cove is off the main channel so no direct boat traffic. It's 10 minutes from Jack Daniels Distillery and the State Park with hiking/biking trails and the fabulous Bear Trace Golf Course. We're on a cul-de-sac in a secluded neighborhood with the best sunsets.

Latitude Adjustment - Lake Cottage
Enjoy the lake with all the amenities you could dream of! At Twin Creeks resort & Marina offers three resort style pools, marina, restaurant all golf cart accessible, designer decorated home with all the comforts of home. Use the golf cart at your leisure, two kayaks for paddling on the lake. Enjoy sunsets on the lake, fires at the firepit, grilling on the patio, hiking around the resort. Family friendly with fold-a-away crib, toys, books and other things to entertain children.

The Modern Mainstay at Barefoot Bay
Welcome to The Modern Mainstay, your stylish retreat by the shores of Tims Ford Lake! This pet friendly contemporary home is just 1/2 mile from the historic downtown square where you can enjoy doing a bit of shopping or dining. Or sit on the front porch with lake views, and take in the serene surroundings. Take a dip in our lakefront community pool. Enjoy access to the lakefront common area for fishing, swimming in the lake, and relaxing by the fire pit with a glass of wine.

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.

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

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.
Popular amenities for house rentals in Winchester
House rentals with a pool

Lakeside Luxe | Lake + Pool Access

TC Easy Breeezee

Lakefront, 3 Boats + Pizza Oven, Gorgeous!

The Old Fashioned w/ lake view & FREE pontoon!

Barefoot Dreams

Forest Retreat: Poolside Bliss Close to Campus

Private indoor pool & sauna

EASY PEASY on Tim's Ford Lake, golf cart, pool
Weekly house rentals

Lake Life

Whitetail Creek Lodge Close to Campus

Long Weekend

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

The Little Lake House @The Retreat at Waters Edge

“The Country” Lake House w/ Private Dock

Lounges at Lynchburg Green House

Reel Simple Lakeside Home w/EV Charger & Golf Cart
Private house rentals

Luxury 3BR lakeside escape

Hydrotherapy Haven

Charming Retreat 5 Min to Tims Ford Lake; Sleeps 8

Timberhill Home-Walk to the Lake!

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

Serene Lake House Retreat with New Golf Cart

Just a short path to the lake! Private dock!

Barefoot Bungalow Bright airy lakeside home
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $255 SGD | $255 SGD | $255 SGD | $228 SGD | $336 SGD | $398 SGD | $406 SGD | $369 SGD | $286 SGD | $288 SGD | $304 SGD | $236 SGD |
| Avg. temp | 5°C | 8°C | 12°C | 17°C | 21°C | 25°C | 27°C | 27°C | 23°C | 17°C | 11°C | 7°C |
Destinations to explore
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- Rentals with a fireplace Winchester
- Pet-friendly rentals Winchester
- Rentals with outdoor seating Winchester
- Rentals with a washing machine and dryer Winchester
- Rentals with a firepit Winchester
- Rentals with a kayak Winchester
- Rentals with lake access Winchester
- Rentals with a patio Winchester
- Family-friendly rentals Winchester
- Rentals with pools Winchester
- Cabin rentals Winchester
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- Cloudland Canyon State Park
- Tennessee Aquarium
- Monte Sano State Park
- Chattanooga Choo Choo
- Coolidge Park
- Rock City
- Hunter Museum of American Art
- South Cumberland State Park
- Creative Discovery Museum
- Raccoon Mountain Caverns & Campground
- Point Park
- Chattanooga Zoo
- U.S. Space & Rocket Center
- Chattanooga Whiskey Experimental Distillery
- Cathedral Caverns State Park
- Dublin Park
- Burritt on the Mountain
- Cumberland Caverns
- Old Stone Fort State Archaeological Park
- Huntsville Botanical Garden
- Lowe Mill Arts And Entertainment
- Finley Stadium
- Von Braun Center, North Hall
- Discovery Center





