Winchester Vacations

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    Save up to SAR 390 when you book a flight and hotel together*
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Find the Best Winchester Vacation Packages

Winchester Hotel Deals

La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is SAR 392 per night from Apr 13 to Apr 14
SAR 392
SAR 427 total
includes taxes & fees
13 Apr - 14 Apr
9/10 Wonderful! (1,904 reviews)
"Nice clean large rooms"

Reviewed on 4 April 2025

La Quinta Inn & Suites by Wyndham Winchester
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is SAR 363 per night from Apr 27 to Apr 28
SAR 363
SAR 395 total
includes taxes & fees
27 Apr - 28 Apr
9.4/10 Exceptional! (1,015 reviews)
"A very convenient location right off the interstate with many food options within walking distance. The gentleman working the front desk was outgoing and welcoming."

Reviewed on 8 April 2025

Comfort Inn & Suites
The George Washington Hotel, A Wyndham Grand Hotel
The George Washington Hotel, A Wyndham Grand Hotel
3.5 out of 5
103 E Piccadilly St, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is SAR 476 per night from Apr 17 to Apr 18
SAR 476
SAR 539 total
includes taxes & fees
17 Apr - 18 Apr
9.2/10 Wonderful! (1,000 reviews)
"Beautiful hotel, super easy check in, restaurant on the property is Unos Pizzeria, just one block away is Old Town and we had an enjoyable evening strolling that area after dinner. We’ve already booked another stay for ‘our stop on the way home.’"

Reviewed on 31 March 2025

The George Washington Hotel, A Wyndham Grand Hotel
See all 1,976 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.

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?
If you’d like to score a cheap Winchester vacation package, consider traveling in December, January and February. You’re likely to find better prices on flights and accommodations during these months — perfect for travelers wishing to save money.
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 travel: Check your schedule and get your bags packed. Your favorite time of year and the activities available will also help you decide when to vacation in Winchester.
  2. Set a budget: Consider expenses such as flights, food and transportation when calculating how much to set aside for your trip to Winchester. Then, pick a property that fits your budget, whether that’s a wallet-friendly option or a more luxurious retreat.
  3. Decide how long to go for: Now that you know more about Winchester, you can figure out the perfect length of your break. Put together a rough plan and give yourself enough time for all the things you want to do.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that’s left is to find a Winchester vacation package that brings all your bookings together.

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

Shenandoah University

4.5/5(69 reviews)

Enjoy the collegiate vibe when you visit Shenandoah University, during your trip to Winchester. While in this walkable area, you can savor the top-notch restaurants.

Shenandoah University