Middleburg Holidays

Photo by Stephanie Sutton
    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to S$120 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

Top hotels in Middleburg

Hyatt Regency Dulles
Hyatt Regency Dulles
4 out of 5
2300 Dulles Corner Blvd, Herndon, VA
Fully refundable
The price is S$244 per night from 3 May to 4 May
S$244
per night
3 May - 4 May
8.6/10 Excellent! (1,005 reviews)
"Very good"

Reviewed on 25 Apr,2024

Hyatt Regency Dulles
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 S$923 per night from 2 May to 3 May
S$923
per night
2 May - 3 May
9/10 Wonderful! (293 reviews)
"Our family stayed at the resort along with another family with a tween and teens. We enjoyed the indoor saltwater pool as well as the archery lesson. The complimentary shuttle was very convenient. We took advantage of the service for dinner at the Goodstone Inn, about a 10 minute drive away. The ..."

Reviewed on 30 Mar,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 S$584 per night from 2 May to 3 May
S$584
per night
2 May - 3 May
9.4/10 Exceptional! (284 reviews)
"Classic"

Reviewed on 22 Apr,2024

The Red Fox Inn & Tavern
See all 921 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.

Frequently asked questions

How much does a Middleburg holiday package cost?
From just , you can build your own Middleburg holiday 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 holiday 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 travellers.
How far in advance should I book my Middleburg holiday?
Travellers 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 holiday is only a couple of clicks away.
Can I choose my airline with a Middleburg Expedia holiday 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 holiday package?
Whether it’s your flight or hotel, you can cancel or change it. Booked your Middleburg holiday 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.

Popular places to visit

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 savour 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 savour the top-notch restaurants.

Chrysalis Vineyards

What to do in Middleburg

Image for Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

S$94
Per adult
Leesburg Premium Outlets Shopping Tour
Image for Historic Leesburg Guided Walking Tour

Historic Leesburg Guided Walking Tour

S$74
Per adult
Historic Leesburg Guided Walking Tour
Image for Virginia Wineries Guided Tour & Tastings from Washington DC

Virginia Wineries Guided Tour & Tastings from Washington DC

S$308
Per adult
Virginia Wineries Guided Tour & Tastings from Washington DC
See all activities in Middleburg
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.