Middleburg Vacations from $260

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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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8/10 Very Good! (792 reviews)
Hotel was just okay. For a non-smoking hotel, the smell of cigarette smoke was still present in the rooms and hallways. The breakfast was minimal and not what I expected given prior reviews.

Reviewed on Jul 3, 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
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.2/10 Very Good! (1,005 reviews)
The good thing is it is on Gallaudet's property.

Reviewed on Jun 23, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
10/10 Exceptional! (3 reviews)
Very difficult to pull up and take advantage of valet parking. Otherwise, everything was AMAZING!

Reviewed on Jun 29, 2025

YOTEL Washington DC

YOTEL Washington DC

4 out of 5
Northwest
Save 100% on your flight
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.4/10 Very Good! (1,950 reviews)
Very clean and comfortable rooms. I love the led lights. The rooftop pool was beautiful and the food/drinks were great!

Reviewed on Jul 4, 2025

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
Save 100% on your flight
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,477 reviews)
Clean and convenient

Reviewed on Jun 24, 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

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.

Chrysalis Vineyards

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
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

$255
per adult
Private Washington DC Virginia Winery Wine Tasting Tour -Spirited
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
$696 nightly
The price is $793 total per night from Jul 6 to Jul 7
$793 total
Jul 6 - Jul 7
Total includes taxes and fees
9/10 Wonderful! (358 reviews)
Top of the Line
"Fabulous service, great food, great rooms, and one of my all time favorite bars!"

Reviewed on Jun 29, 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
$314 nightly
The price is $358 total per night from Jul 13 to Jul 14
$358 total
Jul 13 - Jul 14
Total includes taxes and fees
9.6/10 Exceptional! (368 reviews)
First class
"Great location. Excellent food. A first class property."

Reviewed on Jun 29, 2025

The Red Fox Inn & Tavern
18th Century Stone Cottage minutes from historic Middleburg
18th Century Stone Cottage minutes from historic Middleburg
Middleburg
$367 nightly
The price is $394 total per night from Jul 6 to Jul 7
$394 total
Jul 6 - Jul 7
Total includes taxes and fees
10/10 Exceptional! (44 reviews)
Beautiful Cottage
"We really enjoyed our short stay near Middleburg. The cottage and property are beautiful and the owner was extremely communicative. We will back in the Fall to try some new wineries."

Reviewed on Jun 23, 2025

18th Century Stone Cottage minutes from historic Middleburg
See all 958 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 $260 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.