Winchester vacation rentals

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Best Winchester vacation rentals

Most recommended vacation rentals in Winchester

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3 Bedroom Cozy Home Minutes From Tims Ford Lake - Winchester - Living room
3 Bedroom Cozy Home Minutes From Tims Ford Lake
Winchester, TN
8.6Very good(2)
Parking
Free Wi-Fi
Pet friendly
$236+
Check availability
Beautifully Renovated Studio 2 Miles From Marina! - Winchester - Dining room
Beautifully Renovated Studio 2 Miles From Marina!
Winchester, TN
9.3Wonderful(18)
Parking
Free Wi-Fi
Pet friendly
$147+
Check availability
Beautiful And Spacious Fully Renovated Farmhouse - Winchester - Kitchen
Beautiful And Spacious Fully Renovated Farmhouse
Winchester, TN
9.3Wonderful(26)
Parking
Free Wi-Fi
Pet friendly
$331+
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On the water with Dock & Great Location - Winchester - Kitchen
On the water with Dock & Great Location
Winchester, TN
9.5Wonderful(19)
Free Wi-Fi
Pet friendly
$278+
Check availability
Lake Home Retreat w/Lake/Marina Access Golf Cart - Winchester - Living room
Lake Home Retreat w/Lake/Marina Access Golf Cart
Winchester, TN
9.8Wonderful(10)
Parking
Free Wi-Fi
Pool
$312+
Check availability
The Yellow Cottage By Tims Ford Lake - Winchester - Building
The Yellow Cottage By Tims Ford Lake
Winchester, TN
8.0Very good(17)
$171+
Check availability
Newly Renovated Cozy Place Minutes From The Lake - Winchester - Kitchen
Newly Renovated Cozy Place Minutes From The Lake
Winchester, TN
5.3Fair(5)
Parking
Free Wi-Fi
Pet friendly
$112+
Check availability
Cozy Lake Cottage W/ Kayaks, Sups, Pool & Firepit - Winchester - Kitchen
Cozy Lake Cottage W/ Kayaks, Sups, Pool & Firepit
Winchester, TN
9.7Wonderful(10)
Parking
Free Wi-Fi
Pool
$263+
Check availability
Tim's Ford Lake Home w/ Covered Boat Dock & Jet Ski Port - Newly Remodeled - Winchester - Living room
Tim's Ford Lake Home w/ Covered Boat Dock & Jet Ski Port - Newly Remodeled
Winchester, TN
Free Wi-Fi
Spa
$403+
Check availability
Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc - Winchester - Living room
Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc
Winchester, TN
9.7Wonderful(14)
Parking
Free Wi-Fi
$467+
Check availability
Lakeside Retreat Marina/Pool, Golf Cart, Game Room - Winchester - Living room
Lakeside Retreat Marina/Pool, Golf Cart, Game Room
Winchester, TN
10Wonderful(1)
Parking
Free Wi-Fi
Pool
$437+
Check availability
Lakefront: Dock, Hot Tub, Fire Pit & Home Theater - Winchester - Balcony
Lakefront: Dock, Hot Tub, Fire Pit & Home Theater
Winchester, TN
9.8Wonderful(37)
Parking
Free Wi-Fi
Spa
$1,268+
Check availability
Enjoy fireside sunset & walk to movies, shops, restaurants! - Winchester - Patio
Enjoy fireside sunset & walk to movies, shops, restaurants!
Winchester, TN
9.6Wonderful(30)
Pet friendly
$487+
Check availability
Gorgeous Renovated Home With Large & Private Lot - Winchester
Gorgeous Renovated Home With Large & Private Lot
Winchester, TN
8.2Very good(8)
Parking
Free Wi-Fi
Pet friendly
$280+
Check availability
Quiet Neighborhood Minutes To Parks, Beaches, Boat Launch, Shopping And Dining. - Winchester
Quiet Neighborhood Minutes To Parks, Beaches, Boat Launch, Shopping And Dining.
Winchester, TN
$427+
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Enjoy Farm Life By Tim Fords Lake - Winchester
Enjoy Farm Life By Tim Fords Lake
Winchester, TN
Free Wi-Fi
Pool
Pet friendly
$194+
Check availability
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$0 - $431$431 - $861$861 - $1,291$1,291 - $1,721$1,721+ per night

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Good to know

Low season

May

High season

November

Average price (weeknight)

$183

Average price (weekend night)

$237
Cheapest month to stay with an average 45% drop in price.
Most expensive month to stay with an average 98% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Winchester vacation rental deals

  • Vacation rentals in Winchester are around 18% cheaper than hotels on average. Search here to compare prices for all accommodation types in Winchester.
  • The best vacation rental properties in Winchester are Tim's Ford Lake Home w/ Covered Boat Dock & Jet Ski Port - Newly Remodeled (10.0, 35 reviews), Luxury Estate Center of Tims Ford Lake with Unbeatable Lakefront Views, Dock (10.0, 24), and New! Twin Creeks Marina Resort Southern Charmer (9.9, 21), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Winchester, you should consider visiting during the low season. The cheapest vacation homes in Winchester can be found in May and March.
  • The cheapest night for renting a vacation home in Winchester is Tuesday. In contrast, the most expensive is Wednesday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Winchester for 3 days.

FAQs when booking a vacation home in Winchester

  • How much is a vacation rental for a week in Winchester?

    The average price for a weekly Winchester vacation rental found by KAYAK users in the last 2 weeks is $2,412.

  • How much is a vacation rental for a month in Winchester?

    The average price for a monthly Winchester vacation rental found by KAYAK users in the last 2 weeks is $10,337.

  • What types of vacation rentals are available in Winchester?

    There are loads of different property types that you can make your vacation home in Winchester. You’ll find apartments, cabins, cottages and houses.

  • Are there any pet-friendly vacation rentals in Winchester?

    There are a number of dog and pet-friendly Winchester vacation rentals, with around 16% allowing you to bring your pet along with you.

  • How much is a vacation rental in Winchester for tonight?

    In the last 72 hours, users have found Winchester vacation rentals for tonight for as low as $162. Search here for similar prices

  • How much is a vacation rental in Winchester for this weekend?

    In the last 72 hours, users have found Winchester vacation rentals for this weekend for as low as $154 per night. Search here for similar prices

  • How can I find vacation rentals near me in Winchester?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Winchester?

Our map will help you find the perfect place to stay in Winchester by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Winchester

Winchester vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Winchester. Find cheap vacation homes to rent in Winchester. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Winchester that suits you best.

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