
House holiday rentals in Winchester
Find and book unique houses on Airbnb
Top-rated house rentals in Winchester
Guests agree: These houses are highly rated for location, cleanliness and more.

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.

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.

Mountain's Edge
The Appalachian A-Frame, built in 2024, is right where you want to be! A cozy, stylish home overlooking the gorgeous views of the valley. While being just far enough away to enjoy the benefits of a quiet mountainous getaway, you're also 25 minutes from downtown Chattanooga, TN, where there is an abundance of amazing activities to partake in! It features a comfortable living space, stunning view with a double decker porch, hot tub, fire pit, and plenty of peace and quiet to relax and enjoy!

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.

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

The Old Fashioned @ Twin Creeks Resort w/ Pool!

Stunning Lakefront! Pool, Kayaks, Bikes, Marina!

Lakeside Retreat Marina/Pool, Golf Cart, Game Room

Basecamp Retreat TimsFordLake

Forest Retreat: Poolside Bliss Close to Campus

The Modern Mainstay at Barefoot Bay

Cliffside Luxe Retreat w/Pool, Hot Tub, Views
Weekly house rentals

Sunset Cottage +Dock on Tims Ford Sleeps 12

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

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

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

Catch & Release - Spacious Lakefront Getaway
Private house rentals

TC Easy Breeezee

Whitetail Creek Lodge Close to Campus

Whiskey Trails Cottage

Tim’s Ford Lake 6BR private dock near Twin Creeks

Chic Monteagle Cabin | Scenic Views & Serene Vibes

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

On Water w/ Private Dock, Entire Home, sleeps 14

Cedar Cabin of Lynchburg - 3 miles to Jack Daniels
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $306 AUD | $306 AUD | $306 AUD | $274 AUD | $404 AUD | $478 AUD | $466 AUD | $448 AUD | $402 AUD | $352 AUD | $367 AUD | $324 AUD |
| 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 $138 AUD 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 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
50 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!
Destinations to explore
- Western North Carolina Holiday rentals
- Nashville Holiday rentals
- Atlanta Holiday rentals
- Gatlinburg Holiday rentals
- Charlotte Holiday rentals
- Pigeon Forge Holiday rentals
- Harpeth River Holiday rentals
- Asheville Holiday rentals
- Southern Indiana Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
- Upstate South Carolina Holiday rentals
- Rentals with a kayak Winchester
- Rentals with pools Winchester
- Rentals with outdoor seating Winchester
- Pet-friendly rentals Winchester
- Rentals with lake access Winchester
- Family-friendly rentals Winchester
- Rentals with a fire pit Winchester
- Rentals with a fireplace Winchester
- Rentals with a patio Winchester
- Cabin rentals Winchester
- Rentals with a washing machine and dryer Winchester
- House rentals Franklin County
- House rentals Tennessee
- House rentals United States
- 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