Winchester Vacations

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Your Winchester Vacation

The rich history and small-town feel are just the start of the things Winchester has on offer. Experience the best of this city your way with a tailor-made Winchester vacation package. You'll want to do some exploring during your trip to Winchester. Find time for big-name attractions such as Shenandoah University, Museum of the Shenandoah Valley and Apple Blossom Mall. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Winchester vacation is easy with Expedia.

Discover the most popular places to visit in Winchester

Gardens at Glen Burnie House.

Museum of the Shenandoah Valley

5/5(19 reviews)

You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.

Museum of the Shenandoah Valley
Staircase at Handley Library

Handley Regional Library

5/5(2 reviews)

After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.

Handley Regional Library

Winchester Medical Center

4/5(39 reviews)

Though Winchester Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Winchester while you are here.

Winchester Medical Center

Winchester Hotel Deals

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $75 total per night from Nov 2 to Nov 3
$75 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (1,088 reviews)
"Everything was fine just bed was a little soft for us."

Reviewed on Oct 14, 2025

Travelodge by Wyndham Winchester
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive, Winchester, VA
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $129 total per night from Nov 2 to Nov 3
$129 total
Nov 2 - Nov 3
Total with taxes and fees
9/10 Wonderful! (1,019 reviews)
"Great stay! Would definitely would stay again!"

Reviewed on Oct 10, 2025

Hampton Inn Winchester-University/Mall Area
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $112 total per night from Nov 2 to Nov 3
$112 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (2,189 reviews)
"Great hotel"

Reviewed on Oct 15, 2025

La Quinta Inn & Suites by Wyndham Winchester
See all 2,023 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
27,300
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theater

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Frequently asked questions

How much does a Winchester vacation package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a vacation to Winchester costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winchester?
You can typically find reduced prices and better availability in December, January and February. Take a look at our cheap Winchester vacation packages and you could land some excellent off-season deals.
How many days is enough for Winchester?
Allow around 2 days for your Winchester vacation to really discover everything that makes this place special. Explore key areas, including Old Town Winchester and College Park. Then make a beeline for major sights like Bright Box Theater and Winchester Little Theater. With a good itinerary, you'll be kept busy with room for some rest time too. Want to travel beyond Winchester? Consider squeezing in a day trip or two.
Is it worth booking a vacation package to Winchester?
Winchester is a good vacation destination with attractions like Museum of the Shenandoah Valley among the many things to keep you entertained. Whether you're traveling with the family or planning a trip with friends, a Winchester vacation promises fun for everyone.
How to find the best Winchester package deals?
Begin your search for a Winchester package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Winchester package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winchester escape underway.
Is it cheaper to book a Winchester vacation as a package?
You can enjoy significant savings on your next Winchester retreat by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to browse some great hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winchester?
Enjoy incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Winchester trip.
How to plan a trip to Winchester?

  1. Choose when to go: Check your schedule and get packing. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Winchester.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and meals to experiences and flights. Your hotel will probably be the biggest expense during your trip to Winchester.
  3. Use our trip planning tool to discover Winchester: Research every aspect of your trip to Winchester with this comprehensive planner. Invite your family and friends to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Work out your trip length: Think about how much time you'd like to spend exploring Winchester. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  5. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose a Winchester vacation package that brings all your bookings together.
  6. Book activities and experiences in advance: Whether it's entrance to a big attraction or a walking tour, you won't have to worry about missing out on the best Winchester has to offer. Find all the fun things to do in Winchester with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Winchester vacation packages?
Secure your dream escape to Winchester with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait until payday — we've joined forces with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stay on budget and snap up travel deals while they last.

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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.