
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.

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.

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!

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.

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.

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/ 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.

Homestead Haven
Enjoy your stay at Homestead Haven with a beautiful view of the farm. We have a 72 acre farm and a family business located walking distance from the airbnb. Take a short stroll down the hill to see the lovely plants and meet your host! This 2 bedroom guesthouse is the perfect stay for you and your loved ones. Conveniently located in Winchester, a short drive to the beautiful historic downtown Winchester and Tim’s ford Lake!

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.

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 house rentals in Winchester
House rentals with a pool

Lakefront Haven–Hot Tub & Heated Porch

TC Easy Breeezee

Stunning Lakefront! Pool, Kayaks, Bikes, Marina!

The Old Fashioned @ Twin Creeks Resort w/ Pool!

Basecamp Retreat TimsFordLake

The Modern Mainstay at Barefoot Bay

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

Tennessee Pearl: lakefront-amazing views-lake toys
Weekly house rentals

Timberhill Home-Walk to the Lake!

Tims Ford *FreeUTV/kayaks/canoe*2.5 acres/private

Cedar Cabin of Lynchburg - 3 miles to Jack Daniels

Tims Ford Lake Getaway

Just a short path to the lake! Private dock!

A quiet getaway.

Grand Lakeview: Double decker dock, Fire Pit, Spa

Lakefront 2 bed 2 bath lakehouse in private cove
Private house rentals

Sunset Cottage +Dock on Tims Ford Sleeps 12

Waterfront•Hot Tub•Arcade•Sweetens Cove Lodge

Location, location, location!

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

Our Sweet Little Piece of Tennessee

Haven Forest House

The Little Lake House @The Retreat at Waters Edge

Tim’s Ford Lake 6BR private dock near Twin Creeks
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £152 | £152 | £152 | £136 | £201 | £238 | £242 | £220 | £171 | £167 | £182 | £161 |
| 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 |
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 £68 per night before taxes and fees

Verified guest reviews
Over 2,770 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
40 properties feature pools

Rentals with dedicated workspaces
50 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!
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- Family-friendly rentals Winchester
- Cabin rentals Winchester
- Rentals with a patio Winchester
- Rentals with a washing machine and dryer Winchester
- Rentals with pools Winchester
- Rentals with a firepit Winchester
- Rentals with lake access Winchester
- Rentals with outdoor seating Winchester
- Pet-friendly rentals Winchester
- Rentals with a fireplace Winchester
- Rentals with a kayak Winchester
- House rentals Franklin County
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