Winchester Vacations from $231

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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.
Nashville Airport Marriott

Nashville Airport Marriott

3.5 out of 5
Donelson
Save 100% on your flight
Price was $357, price is now $231 per person
$231
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
8.4/10 Very Good! (1,023 reviews)
Nice clean room; bar was very friendly.

Reviewed on Oct 6, 2025

Hutton Hotel

Hutton Hotel

4.5 out of 5
West End
Save 100% on your flight
Price was $522, price is now $257 per person
$257
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
8.6/10 Excellent! (1,003 reviews)
The Hutton Hotel was very nice. I was super excited to stay there until I walked into my room and find not one but two chewed up tobacco pouches and the bathroom floor looked like it was swept or mopped. And the shower had hair, it’s like the bathroom was never cleaned.

Reviewed on Sep 28, 2025

H&O on Music Row

H&O on Music Row

4 out of 5
Music Row
Save 100% on your flight
Price was $2,038, price is now $1,120 per person
$1,120
per person
Dec 31 - Jan 4
found 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Nashville (BNA)
10/10 Exceptional! (4 reviews)
Good location, really nice apartment.

Reviewed on Jun 28, 2025

1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,025, price is now $597 per person
$597
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.2/10 Wonderful! (860 reviews)
Great staff!! Walking distance to attractions

Reviewed on Oct 4, 2025

The Gilmore, an AvantStay Hotel

The Gilmore, an AvantStay Hotel

4 out of 5
12 South
Save 100% on your flight
Price was $729, price is now $436 per person
$436
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.8/10 Exceptional! (117 reviews)
Very clean and efficient space in the room. Large tv and easy to use. Fancy coffee maker but I eventually figured it out. Younger folks would have no problem with this. Staff very friendly and courtyard was also nice. Staff recommended a restaurant, The Henry, which is an easy 2 min walk. Might have been the best restaurant meal I’ve ever had. Braised ribs!

Reviewed on Oct 9, 2025

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Discover the most popular places to visit in Winchester

Tim's Ford Marina

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.

Tim's Ford Marina

Hammers

Enjoy an outing to Hammers during your stay in Winchester. Stroll along the lakeside or discover the area's mountain views.

Hammers

Expressions

Enjoy an outing to Expressions during your stay in Winchester. Amble around the area's lakeside or experience its musical theater.

Expressions

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
$101 nightly
The price is $116 total per night from Oct 14 to Oct 15
$116 total
Oct 14 - Oct 15
Total with taxes and fees
8.6/10 Excellent! (640 reviews)
"Clean room, friendly staff."

Reviewed on Oct 6, 2025

Best Western Inn
"The Hawk Nest" cabin on Tims Ford Lake

"The Hawk Nest" cabin on Tims Ford Lake

Winchester
$458 nightly
The price is $523 total per night from Oct 11 to Oct 12
$523 total
Oct 11 - Oct 12
Total with taxes and fees
9.4/10 Exceptional! (18 reviews)
"Very cozy and great lake location. We definitely plan to go back."

Reviewed on Sep 22, 2025

"The Hawk Nest" cabin on Tims Ford Lake
Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs

Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs

2 out of 5
Winchester
10/10 Exceptional! (2 reviews)
"This was a great property for our women's retreat! Property was exactly as described!"

Reviewed on Jul 21, 2025

Get rates
Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs
See all 675 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.

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 $231 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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