Middleburg Vacation Packages 2025/2026 from $293

Middleburg flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

SIXTY DC

Downtown Washington D.C.

Save 100% on your flight

per person

Aug 4 - Aug 7

found 7 hours ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking is offered and the front desk is staffed around-the-clock.

Kellogg Conference Hotel at Gallaudet University

Northeast

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per person

Sep 11 - Sep 14

found 23 hours ago

Roundtrip flight included

Denver (DEN) to Washington (DCA)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.

Club Wyndham National Harbor

Save 100% on your flight

per person

Sep 11 - Sep 14

found 23 hours ago

Roundtrip flight included

Denver (DEN) to Washington (DCA)

2 hot tubs, an indoor pool, and a 24-hour gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the seasonal outdoor pool and perks like free WiFi.

Fairfax Marriott at Fair Oaks

Save 100% on your flight

per person

Aug 6 - Aug 11

found 22 hours ago

Roundtrip flight included

Denver (DEN) to Washington (DCA)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a terrace, and a garden are also offered.

The St. Gregory Hotel

Downtown Washington D.C.

Save 100% on your flight

per person

Aug 28 - Sep 1

found 3 hours ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, express check-out, and valet parking. A terrace, limo/town car service, and a lobby fireplace are also on offer.

Top Middleburg hotels deals

Salamander Resort And Spa

500 North Pendleton Street, Middleburg, VA

Free Cancellation

Reserve now, pay when you stay

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A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury resort. Bring the family and enjoy the children's club, children's pool, and arcade/game room. Enjoy the gym and perks like free WiFi.

Pool

Spa

The Red Fox Inn & Tavern

2 E Washington St, Middleburg, VA

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A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. A terrace, a garden, and concierge services are also on offer.

Breakfast included

Parking included

18th Century Stone Cottage minutes from historic Middleburg

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This cottage includes a garden and barbecue grills.

Kitchen

Pet friendly

Hyatt Regency Dulles

2300 Dulles Corner Blvd, Herndon, VA

Free Cancellation

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This hotel features an indoor pool, A 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Pool

Hot Tub

Hyatt Place Herndon Dulles Airport East

13711 Sayward Blvd, Herndon, VA

Free Cancellation

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This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free airport shuttle. Enjoy the 24-hour gym and free buffet breakfast each morning.

Pool

Breakfast included

Wingate by Wyndham Chantilly / Dulles Airport

3940 Centerview Dr, Chantilly, VA

Free Cancellation

Reserve now, pay when you stay

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This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

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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.

Popular places to visit

This winery is fairly new. I think they need a few more years to establish their wine selection. However the wines weren't terrible. I've just had better in this area. But the view from the upper deck is amazing. Definitely worth checking out if you are in the area. Staff is very friendly and knowledgeable. And their sangria was great! #drinkvirginiawine
#winesnob #virginia
#winery #canavineyard
#outdoors

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.

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 trendy area.

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.

Frequently asked questions

How much are vacation packages to Middleburg?

You might be pleasantly surprised --- you could find yourself in Middleburg for as low as $293. Allow Travelocity to save you money and time with our fantastic vacation packages. With flights, hotels and experiences all ready to be snapped up, what's stopping you?

How long should my Middleburg vacation be?

Most sightseers vacation in Middleburg for roughly 2 nights. That being said, travel is all about discovering hidden gems and creating unforgettable memories --- why not book a few additional nights so you can do just that?

Where can I get the best vacation package deals for Middleburg?

There are amazing Middleburg package deals waiting for you with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties across the globe? Keep this in mind when you're ready to tick another place off your must-visit list.

Why should I book my Middleburg vacation bundle via Travelocity?

We make traveling the world easy. Whether you're seeking an amazing new place to roam around or want to ensure you get the best price on offer, we've got you covered. Our 24/7 customer care, quality service and Price Match Guarantee mean you can book with confidence with Travelocity.

Can I save on my Middleburg car rental if I combine it with hotels and flights?

Combining your flight, hotel and car into a Middleburg vacation package is the easiest way to land the best deal. Plus, having your own set of wheels gives you the freedom to find your way to all those landmarks you're itching to see. Located 40 mi from Middleburg, White House is one place that should be on your must-do list. Fasten your seat belt and make a day trip of it.

Which airport is best for Middleburg?

There's a very good chance you'll be arriving at Ronald Reagan Washington National Airport (DCA), located 40 mi east of inner Middleburg. Washington Dulles Intl. Airport (IAD) (16 mi away from central Middleburg) and Baltimore Washington Intl. Thurgood Marshall Airport (BWI) (60 mi away from central Middleburg) are other options.

What is there to do in Middleburg?

While getting off the beaten track is no doubt rewarding, you shouldn't ignore the popular sights that make a place famous. Greenhill Winery & Vineyards and Cana Vineyards and Winery are a couple of them in Middleburg.

Where should I stay when visiting Middleburg?

If you're looking for someplace comfortable to lay your head, have a look at the Magnificent Middleburg Getaway: 2BR w Bucolic Views, Solar Power, & Nearby Shops. It's the top choice for many travelers.