Discover a selection of 165 vacation rentals in Winchester, TN that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $207 per night, and houses and cabins are popular options for a stay in Winchester. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Winchester
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What are the top vacation rentals in or near Winchester?

Whether you want an intimate escape for you and your honey or someplace roomy to fit all your friends, you'll find some top vacation rentals in and around Winchester. Here are a couple to get your inspiration flowing:

  • Take advantage of conveniences like a stovetop and a barbecue grill at Tim's Ford Lake Home With Covered Boat Dock And Jet Ski Port. Located around 7 miles from Winchester, this unique option has 4 bedrooms and is a hit with guests.
  • Alternatively, unpack your suitcase at Beautiful Lake Views At Twin Creeks. Around 1 mile from the heart of Winchester, it has 3 bedrooms and features a lake view and cookware, dishware and utensils.

For even more great options, use the search bar at the top of the page to find the perfect Winchester vacation rental for you.

What are the best three-bedroom vacation rentals in or near Winchester?

If you want a little extra space for your kids (or that last-minute tagalong buddy), a three-bedroom vacation rental will tick all your boxes. Vrbo can help you find all the best options in or near Winchester, beginning with these two:

  • Reserve a few nights at Beautiful Lake Views At Twin Creeks. With amenities such as a restaurant dining guide and a microwave oven, this roomy retreat will have everyone feeling right at home.
  • Spectacular Lake Townhouse At Twin Creeks Resort Walk To Marina And Pool is another top getaway that features three bedrooms. WiFi and a microwave oven are just a couple of things that will help make your stay more comfortable.

Are there vacation rentals with fire pits in or near Winchester?

If you love the idea of cozying up by a campfire but aren't quite as excited about the "camping" part, a vacation rental with a fire pit is where it's at. Enjoy the comforts of home at one of these options in or near Winchester that come with this nice little perk:

  • Chat, laugh and sing with your fam around the fire at Easy Peasy - Lakefront Home Tim’s Ford Lake Golf Cart Seats 6. This retreat offers plenty of other top amenities, such as outdoor furniture and a balcony.
  • Stoke the embers and then savor the relaxed ambiance at Lakeside At Twin Creeks - 7 Minute Walk To Marina. This sought-after escape also offers a barbecue grill and a stovetop.