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
Downtown Nashville
Save 100% on your flight
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nashville (BNA)
9.4/10 Exceptional! (2,092 reviews)
Virgin was a fun and unique property with something for everyone! Our chamber was perfect and met all of our needs! All staff were helpful and knowledgeable and met every expectation.
Reviewed on Jul 1, 2025
Noelle
Downtown Nashville
Save 100% on your flight
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nashville (BNA)
9.4/10 Exceptional! (1,213 reviews)
I absolutely love the Noelle and stay there every time I visit Nashville. My only critique is that the elevators are painfully slow, and the windows on each floor could really benefit from soundproofing.
Reviewed on Jun 30, 2025
Discover the most popular places to visit in Winchester
Tim's Ford Marina
4.5/5(6 reviews)
Bring the kids to Tim's Ford Marina and enjoy the excitement of this amusement park in Winchester. Discover the countryside while you're in the area.
Hammers
4/5(16 reviews)
Enjoy an outing to Hammers during your stay in Winchester. Stroll along the lakeside or discover the area's mountain views.
Expressions
4/5(7 reviews)
Enjoy an outing to Expressions during your stay in Winchester. Amble around the area's lakeside or experience its musical theater.
Winchester Hotel Deals
Best Western Inn
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
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
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak
Winchester
10/10 Exceptional! (8 reviews)
Staycation
"Everything was perfect. We really enjoyed our stay."
Reviewed on Jun 25, 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.