Middleburg Vacations from $248

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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.

The Latest Middleburg vacation packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Washington-Dulles International Airport

Hampton Inn & Suites Washington-Dulles International Airport

2.5 out of 5
Price was $289, price is now $248 per person
$248
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,000 reviews)
This is nice hotel for the price, a bit noisy latw at night, but still good.

Reviewed on Sep 7, 2025

Embassy Suites by Hilton Tysons Corner

Embassy Suites by Hilton Tysons Corner

3.5 out of 5
Save 100% on your flight
Price was $411, price is now $320 per person
$320
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (2,787 reviews)
Staff was very friendly and helpful

Reviewed on Sep 11, 2025

Lansdowne Resort and Spa

Lansdowne Resort and Spa

4 out of 5
Save 100% on your flight
Price was $801, price is now $663 per person
$663
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,005 reviews)
Wonderful establishment with a gorgeous adult pool area. Only drawback is the walls are thin in the rooms so you can hear your neighbor!

Reviewed on Sep 6, 2025

Courtyard by Marriott Tysons McLean

Courtyard by Marriott Tysons McLean

3 out of 5
Price was $387, price is now $325 per person
$325
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (1,013 reviews)
Only 1 elevator functional? Why?? Will not book again.

Reviewed on Sep 10, 2025

Hilton McLean Tysons Corner

Hilton McLean Tysons Corner

4 out of 5
Price was $391, price is now $337 per person
$337
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (1,012 reviews)
Came to town for the Gregory Porter concert at Wolff Trap and couldn’t have picked a better spot, which made getting around super easy. The staff were incredibly friendly and helpful, always ready to answer questions. The place was spotless and peaceful. I felt completely safe throughout my stay. No doubt I’ll be booking here again next time.

Reviewed on Sep 10, 2025

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Discover the most popular places to visit in Middleburg

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.

Cana Vineyards and Winery

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.

Greenhill Winery & Vineyards

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

What to do in Middleburg

Vineyard and Winery Bus Tour from Metro DC

Vineyard and Winery Bus Tour from Metro DC

$110
per adult
Vineyard and Winery Bus Tour from Metro DC
Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

$90
per adult
Leesburg Premium Outlets Shopping Tour
See all activities in Middleburg

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
$575 nightly
The price is $707 total per night from Oct 5 to Oct 6
$707 total
Oct 5 - Oct 6
Total with taxes and fees
9/10 Wonderful! (363 reviews)
"Lovely restful 2 days Unable to book massage and facial they are fully booked. I was told they are booked months in advance."

Reviewed on Aug 28, 2025

Salamander Resort And Spa
Hyatt Place Herndon Dulles Airport East

Hyatt Place Herndon Dulles Airport East

3 out of 5
13711 Sayward Blvd, Herndon, VA
8.2/10 Very Good! (2,482 reviews)
Perfect Stay Every Time
"Anytime I visit my family in Virginia, I make sure I stay at the Hyatt Place Herndon Dulles East on Sayward Blvd. We absolutely love this hotel for it’s location, customer service, cleanliness, comfort and availability."

Reviewed on Sep 8, 2025

Get rates
Hyatt Place Herndon Dulles Airport East
Hyatt Regency Dulles

Hyatt Regency Dulles

4 out of 5
2300 Dulles Corner Blvd, Herndon, VA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $137 total per night from Sep 27 to Sep 28
$137 total
Sep 27 - Sep 28
Total with taxes and fees
8.8/10 Excellent! (1,424 reviews)
"It was ok"

Reviewed on Sep 7, 2025

Hyatt Regency Dulles
See all 972 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.

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Frequently asked questions

How much does a Middleburg vacation package cost?
You can pick up a vacation package to this top destination from $248 on Expedia. However, how much your vacation to Middleburg costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Middleburg?
You're likely to find lower rates and greater availability in March, November and December. Check out our cheap Middleburg vacation packages and you could get some excellent off-season deals.
How many days is enough for Middleburg?
Typically, a few days is great for a Middleburg vacation. With a well-planned itinerary, you can go to all the leading attractions including Chrysalis Vineyards, as well as discover some hidden treasures along the way.
Is it worth booking a vacation package to Middleburg?
Middleburg offers everything you need for an unforgettable getaway. Begin your Middleburg vacation on a high note by visiting top attractions like Glenwood Park.
How to find the best Middleburg package deals?
Use Expedia's filters to help you find some tempting Middleburg package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Middleburg package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Middleburg vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging hotels and flights individually. Better still, you can personalize your Middleburg getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Middleburg?
Enjoy amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Middleburg escape.
How to plan a trip to Middleburg?

  1. Choose when to get away: Check your schedule and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to vacation in Middleburg.
  2. Plan your budget wisely: On top of the price of your stay, you should consider other expenses. These include transportation, flights and food. Also, set aside a little extra for unexpected expenses that may arise during your trip to Middleburg.
  3. Use Expedia's trip planning tool to explore Middleburg: Research every aspect of your trip to Middleburg with this comprehensive planner. Invite friends or family to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Work out your trip length: Think about how much time you'd like to spend exploring Middleburg. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized Middleburg vacation package.
  6. Book activities and experiences ahead of time: Whether it's a ticket to a major attraction or a day trip, you won't have to worry about missing out on Middleburg's best offerings. Find all the incredible things to do in Middleburg with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Middleburg vacation packages?
Jet off on your dream getaway to Middleburg with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait until payday — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans mean you can spread the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily stay on budget and snap up travel deals while they last.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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