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 AED 300 per night from Jan 26 to Jan 27
AED 300
AED 326 total
26 Jan - 27 Jan
includes taxes & fees
9/10 Wonderful! (1,431 reviews)
Clean room. Fan in bathroom was like an airplane engine. Breakfast didn’t start until 6:30 which meant we missed it…. On the road by 6:00….

Reviewed on 7 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 AED 337 per night from Jan 14 to Jan 15
AED 337
AED 367 total
14 Jan - 15 Jan
includes taxes & fees
9.2/10 Wonderful! (2,242 reviews)
Clean room; really comfortable bed. Great staff

Reviewed on 8 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 AED 225 per night from Jan 14 to Jan 15
AED 225
AED 245 total
14 Jan - 15 Jan
includes taxes & fees
8.4/10 Very Good! (1,086 reviews)
C'était propre et tranquille

Reviewed on 11 January 2026

Travelodge by Wyndham Winchester
See all 2,043 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

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

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

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