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.
La Quinta Inn & Suites by Wyndham Washington DC / NoMa

La Quinta Inn & Suites by Wyndham Washington DC / NoMa

2.5 out of 5
Northeast
Save 100% on your flight
per person
Jun. 4 - Jun. 11
found 20 hours ago
Roundtrip flight included
Montreal (YMQ) to Washington (DCA)
7/10 Good! (104 reviews)
Excellent service!! Very clean ! 5 stars !

Reviewed on Mar. 30, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
per person
Jun. 4 - Jun. 11
found 20 hours ago
Roundtrip flight included
Montreal (YMQ) to Washington (DCA)
8.2/10 Very Good! (1,010 reviews)
Great location Nice service

Reviewed on Mar. 30, 2025

Airlie Hotel

Airlie Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun. 20 - Jun. 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Washington (DCA)
8.8/10 Excellent! (280 reviews)
This place is beautiful and amazing. Better than expected. We had a stay.

Reviewed on Mar. 30, 2025

The Royal Sonesta Washington DC Dupont Circle

The Royal Sonesta Washington DC Dupont Circle

4.5 out of 5
Northwest
Save 100% on your flight
per person
Jun. 4 - Jun. 11
found 20 hours ago
Roundtrip flight included
Montreal (YMQ) to Washington (DCA)
8.6/10 Excellent! (1,094 reviews)
The restaurant was ok but the food was only mediocre

Reviewed on Mar. 31, 2025

West End Washington DC, Tapestry Collection by Hilton

West End Washington DC, Tapestry Collection by Hilton

3 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Jun. 4 - Jun. 11
found 20 hours ago
Roundtrip flight included
Montreal (YMQ) to Washington (DCA)
8.6/10 Excellent! (1,002 reviews)
A very average hotel. Nothing compared to the pics Expedia shows on their website. Staff is ok

Reviewed on Jan. 27, 2025

Ready to book your vacation to Middleburg?

 

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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 $823 per night from Apr. 1 to Apr. 2
CA $823
CA $1,013 total
includes taxes & fees
Apr 1 - Apr 2
9/10 Wonderful! (342 reviews)
"Great quick getaway! Wonderful spa and overall amazing experience!"

Reviewed on Mar. 24, 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
The price is CA $464 per night from Apr. 1 to Apr. 2
CA $464
CA $529 total
includes taxes & fees
Apr 1 - Apr 2
9.4/10 Exceptional! (351 reviews)
"The"

Reviewed on Mar. 24, 2025

The Red Fox Inn & Tavern
18th Century Stone Cottage minutes from historic Middleburg
18th Century Stone Cottage minutes from historic Middleburg
Middleburg
The price is CA $394 per night from Apr. 3 to Apr. 4
CA $394
CA $564 total
includes taxes & fees
Apr 3 - Apr 4
9.8/10 Exceptional! (38 reviews)
Relaxing
"Very clean, Beautiful Property. Super peaceful. Will come back in the summer to enjoy town summer time activities."

Reviewed on Mar. 7, 2025

18th Century Stone Cottage minutes from historic Middleburg
See all 932 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?
You can pick up a vacation package to this top destination from CA $1,042 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?
If you’re hoping to book a cheap Middleburg vacation package, consider visiting in January, April and September. You’ll usually find lower prices on hotels and flights during these quieter months — perfect for a budget-friendly break.
How many days is enough for Middleburg?
You can visit all the main attractions in Middleburg within a few days, including the must-see Chrysalis Vineyards. If you’re after a longer Middleburg vacation, look at which kind of activities and day tours are available nearby.
Is it worth booking a vacation package to Middleburg?
Middleburg is a good vacation destination with attractions like Glenwood Park among the many things to keep you busy. Whether you’re heading away with the family or getting away with friends, a Middleburg vacation promises a good time for everyone.
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 go: Check your schedule and get packing. Your preferred time of year and the type of activities on offer will also help you decide when to vacation in Middleburg.
  2. Set your budget: Consider expenses such as flights, food and transportation when calculating how much to put aside for your trip to Middleburg. Then, choose a property that suits your budget, whether that’s a low-cost stay or a high-end retreat.
  3. Decide how long to go away for: Now that you know more about Middleburg, you can figure out the perfect length of your vacation. Pull together a rough itinerary and give yourself enough time for all the things you want to do.
  4. Combine your accommodations and airfare: After you’ve nailed down your trip dates and duration, book the right Middleburg vacation package for you.

Discover the most popular places to visit in Middleburg

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

The Byrne Gallery

You can spend an afternoon exploring the galleries in The Byrne Gallery during your travels in Middleburg. Visit the area's spas, or simply enjoy its restaurants.

The Byrne Gallery

What to do in Middleburg

Vineyard and Winery Bus Tour from Metro DC

Vineyard and Winery Bus Tour from Metro DC

CA $158
per adult
Vineyard and Winery Bus Tour from Metro DC
Celebrate with a winery tour to some of Virginia's best wineries and vineyards by Spirited Tours.

Private Washington DC Virginia Winery Wine Tasting Tour -Spirited

CA $366
per adult
Private Washington DC Virginia Winery Wine Tasting Tour -Spirited
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.