Middleburg Vacations

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Find the Best Middleburg Vacation Packages

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 AED 2,167 per night from May 11 to May 12
AED 2,167
AED 2,661 total
includes taxes & fees
11 May - 12 May
9/10 Wonderful! (344 reviews)
"Overall, I LOVED the property, the friendliness of the staff, amenities (gym, dining options, fire pits, etc.) With that being said, I did noticed the shower door in our room was not cleaned properly and neither was the countertop in the bathroom. I also noticed water leaking around the base of the ..."

Reviewed on 11 April 2025

Salamander Resort And Spa
18th Century Stone Cottage minutes from historic Middleburg
18th Century Stone Cottage minutes from historic Middleburg
Middleburg
The price is AED 1,010 per night from Apr 20 to Apr 21
AED 1,010
AED 1,466 total
includes taxes & fees
20 Apr - 21 Apr
9.8/10 Exceptional! (38 reviews)
Lovely small cottage close to Middleburg
"Great little cozy cottage near Middleburg with great outdoor space and all necessary amenities. Booking, check-in and communication with owner were excellent."

Reviewed on 3 April 2025

18th Century Stone Cottage minutes from historic Middleburg
The Red Fox Inn & Tavern
The Red Fox Inn & Tavern
4 out of 5
2 E Washington St, Middleburg, VA
The price is AED 1,385 per night from Apr 21 to Apr 22
AED 1,385
AED 1,578 total
includes taxes & fees
21 Apr - 22 Apr
9.6/10 Exceptional! (354 reviews)
"Nice"

Reviewed on 6 April 2025

The Red Fox Inn & Tavern
See all 918 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.

Frequently asked questions

How much does a Middleburg vacation package cost?
You can pick up a vacation package to this top destination 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 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

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 relaxing 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