Winchester Holidays

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    Better together
    Save up to HK$1,282 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

Top hotels in Winchester

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 HK$994 per night from 13 Jul to 14 Jul
HK$994
HK$1,136 total
13 Jul - 14 Jul
includes taxes & fees
8.6/10 Excellent! (611 reviews)
"Very nice room with hot tub. Perfect stay, cannot complain about anything"

Reviewed on 17 Jun 2025

Best Western Inn
Spacious Lakefront Retreat w/ Hot Tub + Dock!
Spacious Lakefront Retreat w/ Hot Tub + Dock!
Winchester
9.8/10 Exceptional! (22 reviews)
Great getaway
"Great stay! Everything was as pictured. Will book again, loved access of the lake and dock."

Reviewed on 22 Jun 2025

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Spacious Lakefront Retreat w/ Hot Tub + Dock!
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak
2 out of 5
Winchester
10/10 Exceptional! (8 reviews)
Staycation
"Everything was perfect. We really enjoyed our stay."

Reviewed on 25 Jun 2025

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Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak
See all 645 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.

Popular places to visit

Tim's Ford Marina

Bring the family to Tim's Ford Marina and enjoy the excitement of this theme park in Winchester. Discover the countryside while you're in the area.

Tim's Ford Marina

Frequently asked questions

How much does a Winchester holiday 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 holiday 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 holiday packages. Travelling in less busy months means you can generally find better prices on flights and accommodation.
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 holiday 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 travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Winchester holiday as a package?
An Expedia holiday 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 holiday 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 holiday.
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 personalised Winchester holiday package.

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