
House vacation 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.

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!

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.

Collier House- Nearby to OHV Park & Caverns Venue
Collier House is a 1000 sq ft 2 bedroom, 2 bath home that accommodates 7 guests. We offer luxurious memory foam mattresses and premium bedding, WiFi , and parking to accomodate your ATV. We are happy to make special requests or accommodations. We are centrally located in Coalmont, TN only 5 minutes from the entrance of the OHV off road park. We are located only 15 minutes from the South Cumberland park trailheads and from The Caverns event venue. We are 1 hour away from Chattanooga.

Still Waters Tiny Home: Waterfront/Kayaks/HotTub
Still Waters is a luxury waterfront tiny home created and inspired to bring rest, restoration, and re-connection for your soul. Escape into nature while lounging on one of the spacious decks or sitting around the campfire while admiring the beautiful sunsets or gazing at all the stars. The tiny home sits on 1 acre with large trees encompassing the home with lake access to canoe, kayak, or fish. This is the perfect place to slow down, unwind, and enjoy the beauty of nature all around.

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.

TN Fire 3 bedroom 2 bath beautiful new home
Beautiful 3BR/2bath new barndominium. Walking distance to Historic Lynchburg town square & Jack Daniel's distillery. BR1 Queen bed/private bath, BR2 Queen bed, BR 3 Queen bed, Queen sofa sleeper in LR. 2 Full Baths in home with walk in showers. Full kitchen and washer/dryer. Free/fast wifi & Smart TV. Nice comfortable stay for up to 8 people. Pavilion with barbecue, picnic tables, fire pit. Large side yard, pets must be approved (limit 2, 25 lbs. maximum, $30 pet fee).

"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 Winchester house rentals
House rentals with a pool

Lakefront Haven–Hot Tub & Heated Porch

Lakefront, 3 Fireplaces + Pizza Oven, Gorgeous!

The Old Fashioned @ Twin Creeks Resort w/ Pool!

Stunning Lakefront! Pool, Kayaks, Bikes, Marina!

Barefoot Dreams

Basecamp Retreat TimsFordLake

The Modern Mainstay at Barefoot Bay

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

Cabin by the Bluff

Kayak Kove* DOCK* Lakefront*NEW

Sweet Retreat-across from Twin Creeks Marina

Whitetail Creek Lodge Close to Campus

Whiskey Trails Cottage

The Yellow Cottage by Tims Ford Lake

Remodeled 1940s Cottage Near Square/Lake

A quiet getaway.
Private house rentals

Location, location, location!

Timberhill Home-Walk to the Lake!

Tennessee Whiskey -Cozy Screened Porch + Fireplace

The Little Lake House @The Retreat at Waters Edge

Brand New! Eagle's Nest Tiny House

The Little Lodge Retreat

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

CABIN home near LAKE w NEW HOT TUB
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $277 CAD | $277 CAD | $277 CAD | $248 CAD | $365 CAD | $433 CAD | $442 CAD | $401 CAD | $312 CAD | $305 CAD | $332 CAD | $294 CAD |
| 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 vacation rentals
Explore 90 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at $125 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!
Destinations to explore
- Western North Carolina Vacation rentals
- Nashville Vacation rentals
- Atlanta Vacation rentals
- Gatlinburg Vacation rentals
- Charlotte Vacation rentals
- Pigeon Forge Vacation rentals
- Asheville Vacation rentals
- Southern Indiana Vacation rentals
- Louisville Vacation rentals
- Cincinnati Vacation rentals
- Upstate South Carolina Vacation rentals
- Memphis Vacation rentals
- Rentals with lake access Winchester
- Rentals with a washer and dryer Winchester
- Rentals with a kayak Winchester
- Cabin rentals Winchester
- Rentals with a fireplace Winchester
- Rentals with a patio Winchester
- Family-friendly rentals Winchester
- Rentals with outdoor seating Winchester
- Rentals with pools Winchester
- Rentals with a firepit Winchester
- Pet-friendly rentals Winchester
- House rentals Franklin County
- House rentals Tennessee
- House rentals United States




