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Vacation rentals in Winchester

Vacation rentals in Winchester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Robben's Dwelling - 3 miles from Tim’s Ford Lake
    SUPERHOSTEntire house · 4 guests · 2 beds · 2 bathrooms
    Robben's Dwelling - 3 miles from Tim’s Ford Lake

    Welcome to our spacious, clean, newly renovated private apartment. Whether you are traveling through for business or simply wanting time away, we strive to make your stay comfortable and enjoyable! Conveniently located just outside the town of Winchester, minutes away from Tim's Ford Lake and Twin Creeks Marina and boat rental. (BYOB. Boat parking available) We are 90 miles from Nashville. 40 miles from Huntsville. 17 miles from Sewanee. 19 miles from Jack Daniels Distillery.

    What guests are saying:

    “This is a beautiful “apartment”. Feels like a house. There is a common wall, but once inside, it feels like a house. The rooms are spacious and very nicely decorated. It is super clean and there are tons of added touches, such as snacks, breakfast treats, bottled water, toothbrushes, toothpaste, etc. This is one of the nicest AirBnb’s I’ve stayed in. I would highly recommend it to anyone traveling to the area. It is quiet and conveniently located. Kudos to the hosts!”

  • The Milk Barn Cottage
    SUPERHOSTEntire cottage · 6 guests · 3 beds · 1 bathroom
    The Milk Barn Cottage

    Built in the late 1940's as a working milk barn, the Milk Barn Cottage is 800 sq. ft of cozy comfort. The cottage is near the foot of Monteagle Mountain in the beautiful Pelham Valley. We are half-way between Nashville and Chattanooga, about 2 miles off exit 127 on I-24. The Caverns is about 8 minutes away. Pelham has a coffee shop and quaint restaurants to visit plus all of the natural beauty in our area. We are also just 13 miles from Sewanee and the University of the South.

    What guests are saying:

    “Beautiful little cottage on a dairy farm. Reeda was a wonderful host and met us to put flowers in the cottage upon check in and plenty of local tips. Gave us privacy but was available for any questions. Cottage is an old converted milking building but beautifully done with all the amenities including full kitchen, washer/dryer, TV and wifi. Very relaxing and loved walking around the farm looking at the cows. Nearby cafe, coffee shop, and great hiking. Would definitely stay again.”

  • Dock on Lake! Walk to Downtown Shops/Rest/Movies!
    SUPERHOSTEntire house · 8 guests · 4 beds · 2 bathrooms
    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.

    What guests are saying:

    “This home is awesome! Right on a lake. It was well furnished! The beds were amazingly comfortable, not one person in our group mentioned sleeping poorly! The fishing down in the dock was great too. All in all this was one of the best experiences I've had through air bnb.”

Holiday rentals for every style

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Popular amenities for Winchester holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Winchester

5 Bedroom 3 Bath with Private Dock on Tims Ford
SUPERHOSTEntire house
5 Bedroom 3 Bath with Private Dock on Tims Ford
Price:£278 / night
Newly Renovated Cozy Cottage Minutes From The Lake
Entire flat
Newly Renovated Cozy Cottage Minutes From The Lake
Price:£24 / night
☆Serenity By The Falls☆ Monteagle/Sewanee/Pelham
SUPERHOSTTiny house
☆Serenity By The Falls☆ Monteagle/Sewanee/Pelham
Price:£68 / night
Lovely New Lake View Home at Twin Creeks Marina
SUPERHOSTEntire house
Lovely New Lake View Home at Twin Creeks Marina
Price:£278 / night
Martin Springs Cabin
SUPERHOSTEntire house
Martin Springs Cabin
Price:£48 / night
Holliday Hide Away
Entire cabin
Holliday Hide Away
Price:£72 / night
Small, Cozy, 1900 Studio Cottage
SUPERHOSTEntire guest house
Small, Cozy, 1900 Studio Cottage
Price:£60 / night
Country Cottage Hideaway near Lynchburg
SUPERHOSTEntire cottage
Country Cottage Hideaway near Lynchburg
Price:£87 / night
A Nest at Sewanee-bedroom w/bath, private entrance
SUPERHOSTPrivate room
A Nest at Sewanee-bedroom w/bath, private entrance
Price:£66 / night
Cabin 222: the best in comfort, location, & value
SUPERHOSTEntire cabin
Cabin 222: the best in comfort, location, & value
Price:£60 / night
Pine Bluff Cabin on Tims Ford Lake
SUPERHOSTEntire cabin
Pine Bluff Cabin on Tims Ford Lake
Price:£107 / night
Airstream #73 at The Grove
SUPERHOSTCampervan/Motorhome
Airstream #73 at The Grove
Price:£68 / night
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