
House vacation 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.

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/ streaming tv. Only 3.5 miles off 1-24 exit 127, Pelham, Winchester.

Spacious 4BR/3BA Home Near Tims Ford Lake
Welcome to your beautifully renovated 1940s 4-bedroom, 3-bathroom vacation home near Tims Ford Lake! This spacious historic retreat comfortably sleeps 8 and offers everything you need for a relaxing getaway in Winchester, TN. Enjoy fast Wi-Fi, a Roku Smart TV, and a large private yard perfect for watching the sunrise from the back porch and sunset from the front. Large bedrooms, a cozy reading nook, and a spacious kitchen and living area awaits you!

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–Hot Tub & Heated Porch

TC Easy Breeezee

Lakefront, 3 Fireplaces + Pizza Oven, Gorgeous!

Basecamp Retreat TimsFordLake

Barefoot Dreams

Forest Retreat: Poolside Bliss Close to Campus

The Modern Mainstay at Barefoot Bay

Lovely Lake View Home at Twin Creeks Marina
Weekly house rentals

Visit 100 Aker Woods and Stay at Winnie Cottage!

Whitetail Creek Lodge Close to Campus

Whiskey Trails Cottage

Spacious 4 bedroom 2 bath house king bed in master

Peaceful Getaway on Kayak Way – Winchester

Lakefront 2 bed 2 bath lakehouse in private cove

Catch & Release - Spacious Lakefront Getaway

Travelin’ Light
Private house rentals

Timberhill Home-Walk to the Lake!

*Sommarstuga* Modern cozy lakeview retreat for 6

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

Tennessee Whiskey -Cozy Screened Porch + Fireplace

Cedar Cabin of Lynchburg - 3 miles to Jack Daniels

Tiny Home Escape w/ hot tub + outdoor adventure

Luxe Carriage House - Bluff View

A quiet getaway.
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ735 | ﺩ.ﺇ735 | ﺩ.ﺇ735 | ﺩ.ﺇ657 | ﺩ.ﺇ970 | ﺩ.ﺇ1,149 | ﺩ.ﺇ1,172 | ﺩ.ﺇ1,065 | ﺩ.ﺇ826 | ﺩ.ﺇ830 | ﺩ.ﺇ878 | ﺩ.ﺇ679 |
| 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 ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 2,920 verified reviews to help you choose

Family-friendly vacation rentals
90 properties offer extra space & 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
40 properties have a dedicated workspace

Wi-Fi availability
90 of Winchester vacation rentals include wi-fi 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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- Rentals with a fire pit Winchester
- Pet-friendly rentals Winchester
- Family-friendly rentals Winchester
- Rentals with a washer and dryer Winchester
- Rentals with a kayak Winchester
- Rentals with pools Winchester
- Rentals with lake access Winchester
- Cabin rentals Winchester
- Rentals with a fireplace Winchester
- Rentals with a patio Winchester
- Rentals with outdoor seating Winchester
- House rentals Franklin County
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- Cloudland Canyon State Park
- Tennessee Aquarium
- Monte Sano State Park
- Dublin Park
- Coolidge Park
- Rock City
- Chattanooga Choo Choo
- Hunter Museum of American Art
- Creative Discovery Museum
- Raccoon Mountain Caverns & Campground
- Chattanooga Whiskey Experimental Distillery
- Cathedral Caverns State Park
- Cumberland Caverns
- Burritt on the Mountain
- U.S. Space & Rocket Center
- South Cumberland State Park
- Huntsville Botanical Garden
- Old Stone Fort State Archaeological Park
- Discovery Center
- Chattanooga Zoo
- Short Mountain Distillery
- Lowe Mill Arts And Entertainment
- Point Park
- Von Braun Center, North Hall




