
House vacation 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.

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.

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.

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.

Beautiful Tims Ford lakefront home
Beautiful 3 level lake front home right by the water with no steps to the dock. Plenty of room for large groups of people and great for families with kids. Five bedrooms with a bonus room that has plenty of extra beds. Located less than a mile from public boat ramp. Located in quiet cul-de-sac, on a cove with no wake next to the main channel. If there are any dates that are blocked off that you want please message us because we may have some blocked off dates that we can open up for you.

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.

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.

The Lookout Mountain Birdhouse
Welcome to the Lookout Mountain Birdhouse! This modern cabin in the woods (completed in 2021) is surrounded by stone, trees, and a breath taking view! This house was built to stretch towards the clouds with a 1000 sqft deck and bird's eye view from inside. The 8 foot windows allow for an unobstructed view. The sunset facing view and valley below offer pure relaxation. Watch out for hang gliders and eagles- they love to fly by! Whatever your reason for visiting, this place has it

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.

"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.

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.

Our Catty Shack
Oliver and Lacey (the cats) would love to welcome you to Our Catty Shack! ***NOTE: Our Catty Shack comes WITH CATS*** This spiritual retreat is nestled between imposing ridgelines, abuts a state forest, and faces the powerful Tennessee river. Enjoy dramatic sun and moon rises. Luxuriate in the hot tub. Feast your eyes on the views. Only 15 minutes to downtown Chattanooga - with the peace of the country - have it all here.

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
House rentals with a pool

Lakefront Haven–Fall Escape w/ Firepits + Kayak

TC Easy Breeezee

The Old Fashioned @ Twin Creeks Resort w/ Pool!

Stunning Lakefront! Pool, Kayaks, Bikes, Marina!

Basecamp Retreat TimsFordLake

The Modern Mainstay at Barefoot Bay

Cliffside Luxe Retreat w/Pool, Hot Tub, Views

Gorgeous lake home in Twin Creeks with Lake View
Weekly house rentals

Kayak Kove* DOCK* Lakefront*NEW

Country CharmerNear LakeNEW hot tub:HandicapAccess

Timberhill Home-Walk to the Lake!

Serene Lake House Retreat with New Golf Cart

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

Beautiful cottage next to Tims Ford Lake

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

Cedar Cabin of Lynchburg - 3 miles to Jack Daniels
Private house rentals

Location, location, location!

"Dock Holiday" Retreat on Tim's Ford Lake.

Whitetail Creek Lodge Close to Campus

Sweet Retreat-across from Twin Creeks Marina

Little Green Cottage

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

Forest Retreat: Poolside Bliss Close to Campus

Lake House Dreams
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 $126 CAD 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 and 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
Wifi availability
90 of Winchester vacation 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!
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- Rentals with a patio Winchester
- Family-friendly rentals Winchester
- Rentals with lake access Winchester
- Rentals with pools Winchester
- Rentals with a fireplace Winchester
- Pet-friendly rentals Winchester
- Rentals with a washer and dryer Winchester
- Rentals with a firepit Winchester
- Rentals with outdoor seating Winchester
- Cabin rentals Winchester
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- House rentals Franklin County
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- Tennessee Aquarium
- Cloudland Canyon State Park
- Monte Sano State Park
- Sweetens Cove Golf Club
- Black Creek Club
- The Ledges
- Coolidge Park
- The Lookout Mountain Club
- Chattanooga Golf and Country Club
- Chattanooga Choo Choo
- Old Fort Golf Course
- Creative Discovery Museum
- Hunter Museum of American Art
- National Medal of Honor Heritage Center