
House holiday rentals in Winchester
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Top-rated house rentals in Winchester
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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.

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.

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.

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.

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.

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 Winchester house rentals
House rentals with a pool

Lakefront Haven–Hot Tub & Heated Porch

The Old Fashioned @ Twin Creeks Resort w/ Pool!

Stunning Lakefront! Pool, Kayaks, Bikes, Marina!

Basecamp Retreat TimsFordLake

Forest Retreat: Poolside Bliss Close to Campus

The Modern Mainstay at Barefoot Bay

Lovely Lake View Home at Twin Creeks Marina

Private indoor pool & sauna
Weekly house rentals

Summer Sewanee Lake House

Cabin by the Bluff

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

New Retreat Near Normandy Lake

Cedar Cabin of Lynchburg - 3 miles to Jack Daniels

1940's Cottage Near Square/Lake

Grand Lakeview: Double decker dock, Fire Pit, Spa

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

Location, location, location!

Chic Lake Retreat - Cabin by Lake

Our Sweet Little Piece of Tennessee

Haven Forest House

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

Spacious 4 bedroom 2 bath house

Chic Monteagle Cabin | Scenic Views & Serene Vibes

Beautiful cottage next to Tims Ford Lake
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $356 NZD | $356 NZD | $356 NZD | $319 NZD | $470 NZD | $558 NZD | $568 NZD | $517 NZD | $401 NZD | $392 NZD | $428 NZD | $378 NZD |
| 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 $160 NZD 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!
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- Family-friendly rentals Winchester
- Rentals with lake access Winchester
- Rentals with a fire pit Winchester
- Cabin rentals Winchester
- Pet-friendly rentals Winchester
- Rentals with a kayak Winchester
- Rentals with outdoor seating Winchester
- Rentals with a washing machine and dryer Winchester
- Rentals with a fireplace Winchester
- Rentals with a patio Winchester
- Rentals with pools Winchester
- House rentals Franklin County
- House rentals Tennessee
- House rentals United States
- Cloudland Canyon State Park
- Tennessee Aquarium
- Monte Sano State Park
- Sweetens Cove Golf Club
- Black Creek Club
- The Ledges
- Coolidge Park
- Chattanooga Golf and Country Club
- Chattanooga Choo Choo
- Old Fort Golf Course
- Hunter Museum of American Art
- Creative Discovery Museum
- National Medal of Honor Heritage Center
- Kyujo-mae Station




