Winchester Vacations

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    Better together
    Save up to ￥45,448 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Winchester Vacation Packages

Winchester Hotel Deals

Best Western Inn
Best Western Inn
2.5 out of 5
1602 Dinah Shore Boulevard, Winchester, TN
Fully refundableReserve now, pay when you stay
The price is ￥17,132 per night from Jun 24 to Jun 25
￥17,132
￥19,573 total
Jun 24 - Jun 25
includes taxes & fees
8.6/10 Excellent! (610 reviews)
"Very nice room with hot tub. Perfect stay, cannot complain about anything"

Reviewed on Jun 17, 2025

Best Western Inn
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak
2 out of 5
Winchester
10/10 Exceptional! (7 reviews)
Awesome place
"Nice home very clean a bit of a walk to dock but dock was VERY nice!"

Reviewed on Jun 1, 2025

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Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak
"The Hawk Nest" cabin on Tims Ford Lake
"The Hawk Nest" cabin on Tims Ford Lake
Winchester
The price is ￥28,855 per night from Jun 21 to Jun 22
￥28,855
￥61,500 total
Jun 21 - Jun 22
includes taxes & fees
9.2/10 Wonderful! (14 reviews)
Lovely Peaceful Stay
"We absolutely loved staying here. The owner was very communicative with us.The view and peacefulness was amazing. Close to Winchester if you want to go into town. We truly enjoyed our stay!"

Reviewed on Apr 21, 2025

"The Hawk Nest" cabin on Tims Ford Lake
See all 651 properties in Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices on Expedia for your Winchester escape. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
December, January and February are the best times to look for cheap Winchester vacation packages. Traveling in less busy months means you can generally find better prices on flights and accommodations.
How many days is enough for Winchester?
With a well-planned schedule, you can easily tick off the main Winchester sights in a few days. But if you prefer to venture off the beaten track or go on day tours, consider booking your Winchester vacation for longer.
How to find the best Winchester package deals?
Finding a cheap Winchester package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Winchester package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging hotels and flights separately. Better still, you can tailor your Winchester trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Winchester?
Enjoy amazing discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Winchester vacation.
How to plan a trip to Winchester?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Winchester.
  2. Set your budget: Factor in costs like transportation, flights and meals when calculating how much to put aside for your trip to Winchester. Then, select a property that suits your budget, whether that's an economical stay or a deluxe getaway.
  3. Decide how long to go for: Now that you know more about Winchester, you can work out the ideal length of your break. Pull together a rough plan and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Winchester vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.