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Winchester hotels

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Booking Insights

Best Winchester hotels

Discover the best hotels in Winchester and compare prices, ratings, and locations to find the right stay for your trip.
These are the best prices for Oct 10 - 11.
Best Western Inn - Winchester - Pool
Best Western Inn - Winchester - Pool
Best Western Inn
Winchester, TN
8.1Very good(244)
Parking
Free Wi-Fi
Pool
Pet friendly
$116+
Check availability
Quality Inn - Decherd - Pool
Quality Inn - Decherd - Pool
Quality Inn
Decherd, TN
7.2Good(95)
Free Wi-Fi
Pet friendly
$96+
Check availability
Lady Grey: Original Holders Farmhouse with Jacuzzi - Winchester - Living room
Lady Grey: Original Holders Farmhouse with Jacuzzi - Winchester - Living room
Lady Grey: Original Holders Farmhouse with Jacuzzi
Winchester, TN
10Wonderful(2)
$393+
Check availability
Gorgeous Lake House in Twin Creeks - Marina Side - Winchester - Living room
Gorgeous Lake House in Twin Creeks - Marina Side - Winchester - Living room
Gorgeous Lake House in Twin Creeks - Marina Side
Winchester, TN
9.6Wonderful(12)
Pool
$618+
Check availability
Vintage Q ensuite room, historic railroad hotel - Cowan - Bedroom
Vintage Q ensuite room, historic railroad hotel - Cowan - Bedroom
Vintage Q ensuite room, historic railroad hotel
Cowan, TN
10Wonderful(1)
Free Wi-Fi
$209+
Check availability
Tiny Home w/ RV Hookups - Winchester - Living room
Tiny Home w/ RV Hookups - Winchester - Living room
Tiny Home w/ RV Hookups
Winchester, TN
8.6Very good(9)
Cottage
$177+
Check availability
Spacious Lakeview Townhome, Pet-Friendly w/Dock & Boatslip - Winchester - Patio
Spacious Lakeview Townhome, Pet-Friendly w/Dock & Boatslip - Winchester - Patio
Spacious Lakeview Townhome, Pet-Friendly w/Dock & Boatslip
Winchester, TN
10Wonderful(7)
House
$396+
Check availability

Cheap hotels in Winchester

Find deals on some of our best-value hotels Oct 10 - 11.
3 Bedroom Cozy Home Minutes From Tims Ford Lake - Winchester
3 Bedroom Cozy Home Minutes From Tims Ford Lake
Winchester, TN
8.9Very good(6)
Apartment
Parking
Free Wi-Fi
Pet friendly
$158+
Check availability
The Cozy RV Studio Retreat- Located in the Beloved Lynchburg, TN - Winchester - Patio
The Cozy RV Studio Retreat- Located in the Beloved Lynchburg, TN
Winchester, TN
10Wonderful(1)
Caravan
$160+
Check availability
Oasis on the Square - Winchester - Building
Oasis on the Square
Winchester, TN
9.6Wonderful(12)
Apartment
$173+
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Winchester Home With Views Near Tims For - Winchester
Winchester Home With Views Near Tims For
Winchester, TN
8.0Very good(1)
House
$188+
Check availability
Winchester Home w/ Views Near Tims Ford Lake! - Winchester
Winchester Home w/ Views Near Tims Ford Lake!
Winchester, TN
10Wonderful(1)
House
Parking
Free Wi-Fi
$190+
Check availability
Winchester's Premier Downtown Loft! - Winchester - Kitchen
Winchester's Premier Downtown Loft!
Winchester, TN
9.5Wonderful(8)
Apartment
$193+
Check availability

Hotel deals for the weekend

Some of KAYAK users' favorite hotels with availability on Oct 10 - 11.
Waterfront Oasis On Tims Ford Lake Poola - Winchester - Living room
Waterfront Oasis On Tims Ford Lake Poola
Winchester, TN
9.9Wonderful(46)
House
Free Wi-Fi
$462+
Check availability
Basecamp Retreat Timsfordlake - Winchester - Living room
Basecamp Retreat Timsfordlake
Winchester, TN
9.7Wonderful(17)
House
Parking
Free Wi-Fi
Pet friendly
$276+
Check availability
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family - Winchester - Bedroom
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Winchester, TN
10Wonderful(16)
House
$768+
Check availability
'The Hawk Nest' cabin on Tims Ford Lake - Winchester - Living room
'The Hawk Nest' cabin on Tims Ford Lake
Winchester, TN
9.3Wonderful(21)
Cabin
Free Wi-Fi
$386+
Check availability

Top-rated hotels

Stay at the hotels that our users loved the most Oct 10 - 11.
Tim's Ford Lake Home. Private Boat Dock with Jet Ski Port & 2 Kayaks - Winchester - Living room
Tim's Ford Lake Home. Private Boat Dock with Jet Ski Port & 2 Kayaks
Winchester, TN
10Wonderful(57)
Cottage
Free Wi-Fi
$429+
Check availability
New Home, Dock, Kayaks, Game Room, Water Views - Winchester - Balcony
New Home, Dock, Kayaks, Game Room, Water Views
Winchester, TN
10Wonderful(34)
House
Parking
Free Wi-Fi
$269+
Check availability
Lakefront-Lakeview-Steps To The Water-Tim's Ford Lake Luxury Home & Dock - Winchester - Balcony
Lakefront-Lakeview-Steps To The Water-Tim's Ford Lake Luxury Home & Dock
Winchester, TN
10Wonderful(29)
House
$930+
Check availability
Whispering Waters - Winchester
Whispering Waters
Winchester, TN
10Wonderful(22)
House
Parking
Free Wi-Fi
$425+
Check availability
Tim's Ford Lakefront Home - Winchester - Living room
Tim's Ford Lakefront Home
Winchester, TN
10Wonderful(21)
House
$520+
Check availability
A Little Slice of Heaven - Come see one of Tennessee's best kept secrets - Winchester - Balcony
A Little Slice of Heaven - Come see one of Tennessee's best kept secrets
Winchester, TN
10Wonderful(21)
House
Free Wi-Fi
$841+
Check availability

Popular filters in Winchester hotels

Hotels with parking
Best Western Inn and others
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Hotels with free cancellation
Explore hotel deals with free cancellation in the area
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Hotels with a pool
Best Western Inn, Lady Grey: Original Holders Farmhouse with Jacuzzi and 1 more
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Booking Insights

KAYAK’s insights for hotels in Winchester

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Winchester with confidence.

Which month has the cheapest hotel rates in Winchester?

Hotels are cheapest in Winchester in November, with average rates of $82/night. In comparison, August is the most expensive month, with prices at $508/night.

What is the cheapest day of the week to book a hotel in Winchester?

Tuesday offers the lowest rates in Winchester, with an average nightly price of $107/night. The highest prices are found on Saturday, with average rates at $726/night.

Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

August
April
$108
$145
Cheapest month to stay with an average 26% drop in price.
Most expensive month to stay with an average 57% 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 hotel deals

  • If you’re looking for a cheap hotel in Chattanooga, you should consider visiting during the low season. You'll find cheaper accommodations in Chattanooga in August and November.
  • Hotel room prices vary depending on many factors but you’ll most likely find the best hotel deals in Chattanooga if you stay on a Tuesday. The opposite is true for, Friday, which is usually the most expensive day.
  • How long should you stay? KAYAK users usually book their accommodation in Chattanooga for 3 days.

FAQs when booking a hotel in Winchester

  • Which freebies do KAYAK users look for when booking a hotel in Winchester?

    KAYAK users look for a hotel in Winchester with free breakfast. Hotels with free breakfast in Winchester include Best Western Inn.

  • How do I find a hotel in central Winchester?

    After you launch a hotel search on KAYAK, you can refine your research by neighborhood, which allows you to pick the central Winchester districts. You can also do a search using the city map to choose a specific location, like Winchester city center.

  • How can I find hotels near me?

    Take a look at our extensive hotel map to find the best hotels 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 hotel.

More options for your stay in Winchester

Complete your trip to Winchester

Vacation rentals in Winchester