Winchester Vacations

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Find the Best Winchester Vacation Packages

Winchester Hotel Deals

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
The price is SAR 297 per night from Jan 26 to Jan 27
SAR 297
SAR 323 total
26 Jan - 27 Jan
includes taxes & fees
9/10 Wonderful! (1,418 reviews)
Yep everything was good

Reviewed on 3 January 2026

Microtel Inn & Suites by Wyndham Winchester
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
The price is SAR 371 per night from Jan 11 to Jan 12
SAR 371
SAR 403 total
11 Jan - 12 Jan
includes taxes & fees
9.2/10 Wonderful! (2,242 reviews)
Clean room, nice layout with sink separate from shower/toilet area. Lived the soft reading lights by the bed.

Reviewed on 3 January 2026

La Quinta Inn & Suites by Wyndham Winchester
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
The price is SAR 255 per night from Feb 1 to Feb 2
SAR 255
SAR 277 total
1 Feb - 2 Feb
includes taxes & fees
8.4/10 Very Good! (1,083 reviews)
No need for Air conditioning, parking great

Reviewed on 4 January 2026

Travelodge by Wyndham Winchester
See all 2,041 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.

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 charming coffeehouses or top-notch restaurants 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 charming coffeehouses or top-notch restaurants 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

Frequently asked questions

How do I find cheap flights to Winchester that have flexible change policies?
When it comes to flying these days, flexibility is crucial. That's why we've added a "No change fee" search function to help you track down cheap, flexible tickets to Winchester. It's near the top left of your screen directly underneath the "Flexible change policies" subheading.
Which airlines fly to Winchester?
Take your pick of a selection of airlines that offer flights into or near Winchester. These are a few of the best:

  • American Airlines - 7,098 flights to or near Winchester each month, including 6,885 flights to Ronald Reagan Washington National Airport (DCA) and 212 to Washington Dulles Intl. Airport (IAD) per month.
  • United Airlines - 6,077 flights to or near Winchester each month, including 5,270 flights to Washington Dulles Intl. Airport (IAD) and 806 to Ronald Reagan Washington National Airport (DCA) per month.
  • Delta Air Lines - 1,659 flights to or near Winchester each month, including 1,304 flights to Ronald Reagan Washington National Airport (DCA) and 355 to Washington Dulles Intl. Airport (IAD) per month.

How can I find cheap tickets to Winchester?
You'll always walk away with an amazing deal with Expedia, but our "flexible dates" search function makes it that much easier. Enter your preferred flight date, then click on the flexible dates link above to see the cheapest prices for nearby days. was the best price for a flight to Winchester in the last seven days.
How much is a flight to Winchester?
In the last seven days, round-trip flights to Winchester sold for as little as and reached a maximum cost of . For one-way trips departing from (), the cheapest seat during this same period was only .
What are the most popular airports to fly into in Winchester?
Depending on your carrier and where you're coming from, one of these popular airports will be your entry point to Winchester:

  • Ronald Reagan Washington National Airport (DCA) - 11,147 flights per month.
  • Washington Dulles Intl. Airport (IAD) - 6,388 flights per month.

When is the cheapest time to fly to Winchester?
If you can be flexible with your travel dates to Winchester, leave earlier in the week. The most affordable day to take off is generally Tuesday, closely followed by Monday. Saturday is typically the most expensive day, with many people choosing to fly on the weekend.
How much is a plane ticket to Winchester?
In the last seven days, plane fares ranged between and . Swipe through our fabulous deals to Winchester, make a booking and then get ready for your getaway!
What months are the cheapest to book a flight to Winchester?
To score a fabulous deal to Winchester, book sometime in February when ticket prices are at their cheapest. When's the most expensive time? In the USA, it's December.
How long is a flight to Winchester?
It depends on where in the U.S. You're traveling from. These in-demand domestic routes and their average flight times will give you a clearer picture of how long it'll take to reach Winchester:

  • Boston, MA (BOS-Logan Intl.) to Ronald Reagan Washington National Airport (DCA) - 1 hour and 44 minutes
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Ronald Reagan Washington National Airport (DCA) - 1 hour and 46 minutes
  • Chicago, IL (ORD-O'Hare Intl.) to Ronald Reagan Washington National Airport (DCA) - 1 hour and 51 minutes