Winchester Vacations

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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 AED 384 per night from Apr 20 to Apr 21
AED 384
AED 418 total
includes taxes & fees
20 Apr - 21 Apr
9/10 Wonderful! (1,921 reviews)
Great, except for the breakfasts
"La Quinta is great overall, but not their breakfasts. I appreciate that they offer it, but I couldn’t eat it."

Reviewed on 10 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 AED 359 per night from May 11 to May 12
AED 359
AED 391 total
includes taxes & fees
11 May - 12 May
9.2/10 Wonderful! (1,003 reviews)
"Very clean hotel!! Front desk staff was friendly. Bed was quite firm, so if you're used to something soft it might be uncomfortable for you. I do wish there had been a fan setting on the heating/cooling unit. I like to have a little white noise to drown out exterior noise while I sleep. The area ..."

Reviewed on 10 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
The price is AED 438 per night from May 4 to May 5
AED 438
AED 496 total
includes taxes & fees
4 May - 5 May
9.2/10 Wonderful! (1,000 reviews)
Fabulous
"Historical hotel in heart of Winchester, steps from Old Town. Really felt luxurious ~ credit to all involved. Keep up the good work."

Reviewed on 15 April 2025

The George Washington Hotel, A Wyndham Grand Hotel
See all 1,977 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