
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.

Entire home in Morrison/Viola
Relax with the whole family in a 130 yr old newly renovated home located at the foothills of the Cumberland Plateau, tucked away in the small, quiet town of Viola. Enjoy the small-town feel with close proximity to Bersheba Springs, Fall Creek Falls, Isha Yoga, & South Cumberland State Park. Less than an hr to Jack Daniel's & George Dickel distillery. The home has -2 separate bedrooms, located on the main floor. Loft with trundle. Full bathroom. Washer/dryer. Full kitchen with dining room.

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.

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.

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*

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

Lakefront Haven–Hot Tub & Heated Porch

TC Easy Breeezee

Beautiful New Construction Lakefront!

Barefoot Dreams

Basecamp Retreat TimsFordLake

Forest Retreat: Poolside Bliss Close to Campus

The Modern Mainstay at Barefoot Bay

Cliffside Infinity Pool • Hot Tub • Epic Views
Weekly house rentals

Visit 100 Aker Woods and Stay at Winnie Cottage!

Timberhill Home-Walk to the Lake!

Haven Forest House

Whiskey Trails Cottage

Tennessee Whiskey -Cozy Screened Porch + Fireplace

Spacious 4 bedroom 2 bath house king bed in master

Best Home on Tims Ford - Private Dock - Hot Tub

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

Location, location, location!

Kayak Kove* DOCK* Lakefront*NEW

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

Cottage on Cedar

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

Just a short path to the lake! Private dock!

Catch & Release - Spacious Lakefront Getaway

Stay Awhile @ Trailhead Cabins
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £149 | £149 | £149 | £133 | £196 | £233 | £237 | £216 | £167 | £164 | £179 | £158 |
| 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 £22 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 & 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
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!
Destinations to explore
- Western North Carolina Holiday rentals
- Nashville Holiday rentals
- Atlanta Holiday rentals
- Gatlinburg Holiday rentals
- Charlotte Holiday rentals
- Pigeon Forge Holiday rentals
- Asheville Holiday rentals
- Southern Indiana Holiday rentals
- Louisville Holiday rentals
- Upstate South Carolina Holiday rentals
- Cincinnati Holiday rentals
- Memphis Holiday rentals
- Rentals with lake access Winchester
- Cabin rentals Winchester
- Rentals with a washing machine and dryer Winchester
- Pet-friendly rentals Winchester
- Rentals with a patio Winchester
- Rentals with pools Winchester
- Rentals with a firepit Winchester
- Rentals with a fireplace Winchester
- Family-friendly rentals Winchester
- Rentals with outdoor seating Winchester
- Rentals with a kayak Winchester
- House rentals Franklin County
- House rentals Tennessee
- House rentals United States
- Cloudland Canyon State Park
- Tennessee Aquarium
- Monte Sano State Park
- Dublin Park
- Rock City
- Coolidge Park
- Chattanooga Choo Choo
- Hunter Museum of American Art
- Creative Discovery Museum
- Von Braun Center, North Hall
- South Cumberland State Park
- Tims Ford State Park
- U.S. Space & Rocket Center
- Lowe Mill Arts And Entertainment
- Huntsville Botanical Garden
- Burritt on the Mountain
- Cathedral Caverns State Park
- Point Park
- Raccoon Mountain Caverns & Campground
- Finley Stadium
- Chattanooga Whiskey Experimental Distillery
- Chattanooga Zoo
- Jack Daniel's Distillery
- Old Stone Fort State Archaeological Park




