Middleburg Vacations from $383

Book a Hotel + Flight or Car together to unlock savings

Photo by Stephanie Sutton
Choose one or more items to build your trip:
    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to $580 when you book a flight and hotel together*
  • lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Middleburg Vacation

Put together a custom vacation package to Middleburg and get ready to experience this exciting city on your own terms. Think about staying in the neighborhood of Stone Ridge, which is good for walking and much more. You'll want to go sightseeing during your trip to Middleburg. Find time for major attractions such as Greenhill Winery & Vineyards, Chrysalis Vineyards and Cana Vineyards and Winery. Stop daydreaming and start doing. Browse the broad range of options on Expedia today and put your Middleburg vacation plans into gear!

The Latest Middleburg Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Aug 1 - Aug 4
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.6/10 Excellent! (1,512 reviews)
It’s periodic foyer was so inviting

Reviewed on May 15, 2024

Hyatt Place National Harbor

Hyatt Place National Harbor

3 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 23
Roundtrip flight included
Boston (BOS) to Washington (DCA)
9.2/10 Wonderful! (1,485 reviews)
It was awesome…wish I could’ve stayed longer!

Reviewed on May 15, 2024

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
Save 100% on your flight
per person
Jul 11 - Jul 14
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (2,003 reviews)
It took 15 of running the water to get hot water for my shower and even though my ac was set at 68 the room temp never got below 71 even after a call to maintenance.

Reviewed on May 14, 2024

The Melrose Georgetown Hotel

The Melrose Georgetown Hotel

4 out of 5
Northwest
Save 100% on your flight
per person
Jul 3 - Jul 8
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,757 reviews)
Overall our experience was decent at the Melrose, aside from there being obvious blood drops on the wall/door frame in our bathroom. When I told the front desk clerk about this and showed her a picture her only response was “so do you want your room cleaned?” with no apology of any kind. Having body fluids, especially blood left on a hotel wall shows there is a lack of attention to cleanliness in these rooms.

Reviewed on May 14, 2024

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Jul 11 - Jul 14
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (1,008 reviews)
The staff was very nice. The balcony was nice.

Reviewed on May 15, 2024

Middleburg Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Washington Dulles Intl. Airport (IAD)
Population
810
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Greenhill Winery & Vineyards, Chrysalis Vineyards and Cana Vineyards and Winery

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 $550 per night from May 19 to May 20
$550
$679 total
includes taxes & fees
May 19 - May 20
9/10 Wonderful! (294 reviews)
"The staff was very friendly and the place was very nice and clean"

Reviewed on Apr 30, 2024

Salamander Resort And Spa
The Red Fox Inn & Tavern
The Red Fox Inn & Tavern
4 out of 5
2 E Washington St, Middleburg, VA
The price is $377 per night from May 19 to May 20
$377
$430 total
includes taxes & fees
May 19 - May 20
9.4/10 Exceptional! (290 reviews)
"We loved our one-night stay. The service was fantastic. We got an upgrade from our original room for a minor issue, but are grateful to you for that."

Reviewed on May 13, 2024

The Red Fox Inn & Tavern
Best Western Dulles Airport Inn
Best Western Dulles Airport Inn
2.5 out of 5
45440 Holiday Drive, Sterling, VA
Fully refundableReserve now, pay when you stay
The price is $101 per night from May 27 to May 28
$101
$115 total
includes taxes & fees
May 27 - May 28
8.2/10 Very Good! (1,007 reviews)
"I have stayed at this hotel before and the rooms are unusually nice. However, the common areas like the walkways have been pretty dirty both times I've stayed."

Reviewed on May 12, 2024

Best Western Dulles Airport Inn
See all 923 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Middleburg vacation package cost?
From just $383, you can build your own Middleburg vacation package. Simply bundle hotels, flights and car rentals and we’ll reward you with discounts.
How do I get a cheap travel package to Middleburg?
Bundle your hotel and flight bookings, throw in extras such as a rental car or activities, and save with a Middleburg vacation package. You won’t just score exciting discounts on your adventure — you’ll have plenty of choice at your fingertips too. When you book with Expedia, you can select from more than 550 air carriers and 1,000,000 hotels around the world. Your next grand adventure starts right here, right now!
Where should I stay in Middleburg?
Stay close to the action. Many people book hotels around popular sights, such as Greenhill Winery & Vineyards, Chrysalis Vineyards and Cana Vineyards and Winery.
What are the top hotels in Middleburg?
If it’s your first time in Middleburg, reserve a room at The Red Fox Inn And Tavern or Littlefield Cottage. Both hotels offer comfy beds and are popular options with lots of travelers.
How far in advance should I book my Middleburg vacation?
Travelers are usually able to compare international flights on Expedia up to 12 months prior to departure. Booking at the last minute? With a little bit of luck, it’s still possible to score a cheap ticket only weeks before your journey.
What does an Expedia Middleburg travel package include?
It all depends on what type of trip you have in mind. Middleburg travel deals can include flights, car rentals and hotels. You can mix and match to create the travel package that suits you. You can also add on experiences and activities after you’ve booked to get even bigger discounts.
What should I know before booking a Middleburg travel package?
You can save big by combining your airfares, hotels and rental cars. Once you’ve made your booking, add on fun stuff like day tours or experiences. Your next unforgettable vacation is only a couple of clicks away.
Can I choose my airline with a Middleburg Expedia vacation package?
Definitely. Expedia has over 550 airline partners to pick from across the world. With so much choice, finding the right carrier to whisk you off to Middleburg shouldn’t be hard.
If I'm not able to travel, can I cancel my Middleburg vacation package?
Whether it’s your flight or hotel, you can cancel or change it. Booked your Middleburg vacation package in the last 24 hours? You may be able to make any changes for free. For bookings made more than 24 hours ago, you may be charged a fee by your hotel, airline or car rental company. For more details, take a look at our Customer Service Portal. We’re here to help you each step of the way.

Discover the most popular places to visit in Middleburg

Image for Cana Vineyards and Winery

Cana Vineyards and Winery

You can enjoy a tasting or tour at Cana Vineyards and Winery during your travels to Middleburg. While in this trendy area, you can savor the top-notch restaurants.

Cana Vineyards and Winery
Image for Greenhill Winery & Vineyards

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
Image for Chrysalis Vineyards

Chrysalis Vineyards

4/5(2 reviews)

You can enjoy a tasting or tour at Chrysalis Vineyards during your travels to Middleburg. While in this trendy area, you can savor the top-notch restaurants.

Chrysalis Vineyards

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.