Middleburg Vacations from $185

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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.
Home2 Suites By Hilton Ashburn, Va

Home2 Suites By Hilton Ashburn, Va

3 out of 5
Price was $272, price is now $185 per person
$185
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Washington (IAD)
No reviews
Newly opened hotel (3 days) and it was an excellent stay! Management and staff were professional and very accommodating. Hotel room was beautiful and spacious. Breakfast was great (hot and cold) with many offerings.

Reviewed on Dec 22, 2025

YOTEL Washington DC

YOTEL Washington DC

4 out of 5
Northwest
Save 100% on your flight
Price was $1,113, price is now $688 per person
$688
per person
Mar 15 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (IAD)
8.2/10 Very Good! (2,262 reviews)
The room was nice, clean, quiet, and we got a nice view. The staff were very friendly, the area was safe, and it was within walking distance of Union Station, the museums, and dining areas. Definitely, I would book the same hotel for a future trip.

Reviewed on Dec 27, 2025

Hilton McLean Tysons Corner

Hilton McLean Tysons Corner

4 out of 5
Save 100% on your flight
Price was $681, price is now $467 per person
$467
per person
Feb 23 - Feb 26
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Washington (IAD)
8.6/10 Excellent! (1,000 reviews)
Hotel need to upgrade a policy for early check out and better information about NO REFUND

Reviewed on Dec 24, 2025

Placemakr Buzzard Point

Placemakr Buzzard Point

2.5 out of 5
Southwest
Save 100% on your flight
Price was $1,031, price is now $721 per person
$721
per person
Mar 15 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (IAD)
9.4/10 Exceptional! (86 reviews)
Very clean and safe apartment. If I knew it was this secluded, I may have chosen an actual Hotel instead of this situation, but it was a beautiful place, great pricing, very close to the National Mall.

Reviewed on Dec 27, 2025

Residence Inn Alexandria Old Town South at Carlyle

Residence Inn Alexandria Old Town South at Carlyle

3 out of 5
Eisenhower East
Save 100% on your flight
Price was $598, price is now $432 per person
$432
per person
Feb 11 - Feb 18
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Washington (IAD)
8.8/10 Excellent! (1,005 reviews)
Clean and spacious. Friendly staff and walking distance to metro! Family friendly! Was perfect!

Reviewed on Dec 4, 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 Dover. While in this trendy area, you can savor the top-notch restaurants.

Cana Vineyards and Winery

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

Red Fox Fine Art

You can spend an afternoon studying the exhibits at Red Fox Fine Art during your travels in Middleburg. Visit the area's spas, or simply enjoy its restaurants.

Red Fox Fine Art

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
$555 nightly
The price is $632 total per night from Jan 7 to Jan 8
$632 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
9.2/10 Wonderful! (374 reviews)
Yes

Reviewed on Dec 26, 2025

Salamander Resort And Spa
The Red Fox Inn & Tavern

The Red Fox Inn & Tavern

4 out of 5
2 E Washington St Middleburg VA
$335 nightly
The price is $382 total per night from Jan 1 to Jan 2
$382 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.6/10 Exceptional! (410 reviews)
Everything was great except the breakfast! A breakfast burrito in your room is no substitute for a decent sit down breakfast. This is not in line with four star friendly accommodation and a four star price. No return visit.

Reviewed on Dec 25, 2025

The Red Fox Inn & Tavern
HYATT house Sterling/Dulles Airport-North

HYATT house Sterling/Dulles Airport-North

3 out of 5
45520 Dulles Plz Sterling VA
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $120 total per night from Jan 3 to Jan 4
$120 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
Love the staff! Comfortable rooms and perfect location.

Reviewed on Dec 19, 2025

HYATT house Sterling/Dulles Airport-North
See all 965 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.

Find the Best Middleburg Vacation Packages

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

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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 $185 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.

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