Middleburg Vacation Packages

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Your Middleburg Vacation

With every last detail planned before you go away, our Middleburg vacation packages mean you can focus more on letting the good times roll. Whether you stay in the neighborhood of Stone Ridge, which is good for walking, or someplace else in town, this lively city promises a world of discoveries. You'll want to take in the sights during your trip to Middleburg. Carve out some time for major attractions such as Greenhill Winery & Vineyards, Cana Vineyards and Winery and Chrysalis Vineyards. A few quick clicks is all it takes to put together the ultimate Middleburg vacation on Expedia.

Top Middleburg Vacation Deals

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.
per person
Jul. 11 - Jul. 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.6/10 Excellent! (1,534 reviews)
Great place and close to everything, clean and tidy, but no drinking water available even a coffee machine inside the room.

Reviewed on Jun. 3, 2024

The Graham Georgetown

The Graham Georgetown

4 out of 5
Georgetown
Save 100% on your flight
per person
Jul. 11 - Jul. 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.8/10 Excellent! (1,335 reviews)
Great place to stay in the heart of Georgetown.

Reviewed on Jun. 2, 2024

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
Save 100% on your flight
per person
Jul. 10 - Jul. 14
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.8/10 Excellent! (2,020 reviews)
All necessary things are within walking distance from the hotel

Reviewed on May 30, 2024

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Jul. 11 - Jul. 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
9.4/10 Exceptional! (1,236 reviews)
The staff was pleasant and professional. The property was walking distance to the National Gallery of Art (our primary destination), excellent restaurants and the Metro. Our room had no view, the bathroom was tiny (hard to exit) and our shower was missing half the sliding door. By design? If so, never seen that before. Excellent in- room coffee and the hotel cafe food was also excellent.

Reviewed on May 25, 2024

InterContinental Washington D.C. - The Wharf, an IHG Hotel

InterContinental Washington D.C. - The Wharf, an IHG Hotel

5 out of 5
The Wharf
Save 100% on your flight
per person
Jul. 11 - Jul. 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
9.2/10 Wonderful! (1,002 reviews)
Enjoyed a concert at THE ANTHEM— a very cool venue.

Reviewed on Jun. 1, 2024

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 CA $750 per night from Jun. 30 to Jul. 1
CA $750
CA $925 total
includes taxes & fees
Jun 30 - Jul 1
9/10 Wonderful! (295 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 CA $514 per night from Jun. 11 to Jun. 12
CA $514
CA $586 total
includes taxes & fees
Jun 11 - Jun 12
9.4/10 Exceptional! (295 reviews)
Great place to escape the big city
"A great place to spend a couple of days escaping big cities."

Reviewed on May 27, 2024

The Red Fox Inn & Tavern
Hyatt Regency Dulles
Hyatt Regency Dulles
4 out of 5
2300 Dulles Corner Blvd, Herndon, VA
Fully refundable
The price is CA $176 per night from Jun. 28 to Jun. 29
CA $176
CA $199 total
includes taxes & fees
Jun 28 - Jun 29
8.6/10 Excellent! (1,004 reviews)
"Clean and quiet"

Reviewed on May 28, 2024

Hyatt Regency Dulles
See all 906 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Middleburg vacation package cost?
From just CA $762, 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

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

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.