Middleburg Vacations

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Find the Best Middleburg Vacation Packages

Middleburg Hotel Deals

Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
The price is AED 2,185 per night from Mar 1 to Mar 2
AED 2,185
AED 2,682 total
1 Mar - 2 Mar
includes taxes & fees
9/10 Wonderful! (378 reviews)
Room was awesome, amazing experiences at the resort and really great customer service

Reviewed on 18 January 2026

Salamander Resort And Spa
18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg

Middleburg VA
The price is AED 1,010 per night from Feb 10 to Feb 11
AED 1,010
AED 1,446 total
10 Feb - 11 Feb
includes taxes & fees
9.8/10 Exceptional! (55 reviews)
Loved out stay!

Reviewed on 26 December 2025

18th Century Stone Cottage minutes from historic Middleburg
The Red Fox Inn & Tavern

The Red Fox Inn & Tavern

4 out of 5
2 E Washington St Middleburg VA
9.4/10 Exceptional! (424 reviews)
Room was wonderful except the thermostat did not work and the room became very hot. Had to open a window. No screen on the window either. Would have been nice to have a refrigerator in the room too. Loved the ice which was in the room and delivered again. Room was lovely though. Not a big fan of ...

Reviewed on 29 January 2026

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The Red Fox Inn & Tavern
See all 993 properties in Middleburg
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 Middleburg

Red fox in winter, Japan. Red Fox in winter landscape. Japanese winter landscape with the animal.

Red Fox Fine Art

You can spend an afternoon studying the exhibits at Red Fox Fine Art during your travels in Middleburg. Visit the area's spas, or simply enjoy its restaurants.

Red Fox Fine Art
Tranquil Glenwood Pond landscape with water dam, green forest hill, and white summer cloudscape in Prince Edward Island, Canada

Glenwood Park

5/5(1 review)

Explore the great outdoors at Glenwood Park, a lovely green space in Middleburg. Visit the area's spas, or simply enjoy its restaurants.

Glenwood Park

Greenhill Winery & Vineyards

3.5/5(3 reviews)

You can enjoy a tasting or tour at Greenhill Winery & Vineyards during your travels to Middleburg. Discover the bars and entertainment venues in this relaxing area.

Greenhill Winery & Vineyards

Frequently asked questions

How do I find cheap flights to Middleburg that have flexible change policies?
When it comes to flying these days, flexibility is essential. That's why we have a "No change fee" search function to help you find flexible, low-cost tickets to Middleburg. It's near the top left of your screen just underneath the "Flexible change policies" heading.
Which airlines fly to Middleburg?
Choose from various airlines that operate flights into or near Middleburg. Here are some of the best of them:

  • American Airlines - 7,098 flights to or near Middleburg 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 Middleburg 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 Middleburg 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 Middleburg?
You'll always score a terrific deal with Expedia, but our "flexible dates" feature makes it even easier. Enter your preferred travel 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 Middleburg in the last seven days.
How much is a flight to Middleburg?
There were loads of cheap fares up for grabs in the last seven days, with the cost of a return flight to Middleburg ranging between and . Many lucky travelers purchased one-way seats from () for only .
What are the most popular airports to fly into in Middleburg?
Depending on which airline you travel with and where you're flying from, one of these well-known airports will be your gateway to Middleburg:

  • 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 Middleburg?
Flying on a Tuesday, followed by a Monday, is usually the best way to pick up the cheapest flight. Steer clear of the weekend if you can, because Saturday is typically the most expensive day. Spend the funds you saved having a ball in Middleburg instead!
How much is a plane ticket to Middleburg?
In the last seven days, airfares ranged between and . Take a look at our unbeatable deals to Middleburg, pick your favorite and then start packing your suitcase.
What months are the cheapest to book a flight to Middleburg?
February is the top month to grab a fabulous deal to Middleburg. Keep in mind that the priciest time to make a purchase in the States isn't the middle of summer, but the month of December.
How long is a flight to Middleburg?
It depends on a number of things, such as your point of departure and whether it's a direct or multi-stop flight. Listed below are some of the most popular domestic routes to Middleburg and their average flight times:

  • 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