Winchester Vacations from $496

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Your Winchester Vacation

The rich history and spectacular views are just the start of the things Winchester has on offer. Experience the very best of this interesting city your way with a tailor-made Winchester vacation package. Any trip to Winchester should include some sightseeing. Hammers is a great place to kick things off. Whoever you're going away with and whatever you want to spend, your dream Winchester vacation is just a few clicks away with Expedia.

The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Virgin Hotels Nashville
1 Hotel Nashville
Bobby Hotel
Noelle
The Monroe by AvantStay – Stylish Group Stay with Easy Access to Attractions
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Discover the most popular places to visit in Winchester

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
$127 nightly
The price is $145 total per night from Jul 6 to Jul 7
$145 total
Jul 6 - Jul 7
Total includes taxes and fees
8.6/10 Excellent! (611 reviews)
"Very nice room with hot tub. Perfect stay, cannot complain about anything"

Reviewed on Jun 17, 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 Jun 22, 2025

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 Jun 25, 2025

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

Find the Best Winchester Vacation Packages

Winchester Essential Information

Language
English
Currency
U.S dollars
Population
8,500
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Tims Ford State Park, University of the South and Tims Ford Lake

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Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from $496 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?
If you'd like to book a cheap Winchester vacation package, consider planning a trip in October, November and December. You'll typically find better prices on hotels and airfares during these quieter months --- perfect for a budget-friendly break.
How many days is enough for Winchester?
The ideal length of your Winchester vacation depends on what you'd like to do and see. Usually, a few days to a week will give you plenty of time to hit all the main sights and explore some hidden gems along the way.
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.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
Your Winchester getaway is meant to be an escape from your daily routine, not a source of money-related stress. So to allow you a bit more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.