Middleburg Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to Rp16.000.000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Middleburg

Salamander Middleburg

Salamander Middleburg

5 out of 5
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
The price is Rp11.192.569 per night from 8 Nov to 9 Nov
Rp11.192.569
Rp13.699.071 total
8 Nov - 9 Nov
includes taxes & fees
Salamander Middleburg
The Red Fox Inn & Tavern

The Red Fox Inn & Tavern

4 out of 5
2 E Washington St Middleburg VA
The price is Rp8.358.927 per night from 22 Nov to 23 Nov
Rp8.358.927
Rp9.529.104 total
22 Nov - 23 Nov
includes taxes & fees
The Red Fox Inn & Tavern
Goodstone Inn & Restaurant

Goodstone Inn & Restaurant

4 out of 5
36205 Snake Hill Road Middleburg VA
The price is Rp4.846.224 per night from 30 Nov to 1 Dec
Rp4.846.224
Rp7.937.453 total
30 Nov - 1 Dec
includes taxes & fees
Goodstone Inn & Restaurant
See all 1,007 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.

Stay near popular Middleburg attractions

A red fox standing in the snow.

Red Fox Fine Art

9.6/10 (10 reviews)
America's leading gallery for sporting art, Red Fox Fine Art showcases exquisite 19th and 20th-century paintings and sculptures. Browse the curated collection that celebrates equestrian heritage in an intimate setting.
See properties

What to do in Middleburg

Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

Rp1.796.600
per adult
Leesburg Premium Outlets Shopping Tour
Luxe Day Trip: 3 VA Wineries & Optional Tasting-Inclusive Upgrade

Loudoun County 3-Winery Tour from DC Metro or Leesburg

Rp2.155.740
per adult
Loudoun County 3-Winery Tour from DC Metro or Leesburg
Guided Thrift Store Walking Tour in Historic Leesburg

Guided Thrift Store Walking Tour in Historic Leesburg

Rp875.550
per adult
Guided Thrift Store Walking Tour in Historic Leesburg
See all activities in Middleburg

Frequently asked questions

How much does a Middleburg holiday package cost?
You can pick up a holiday package to this top destination on Expedia. However, how much your holiday 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 holiday 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 holiday, look at which kind of activities and day tours are available nearby.
Is it worth booking a holiday package to Middleburg?
Middleburg is a good holiday 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 holiday 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 holiday package as early as possible.
Is it cheaper to book a Middleburg holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging hotels and flights individually. Better still, you can personalise 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 holiday 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 holiday 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 holiday. Pull together a rough itinerary and give yourself enough time for all the things you want to do.
  4. Combine your accommodation and airfare: After you've nailed down your trip dates and duration, book the right Middleburg holiday package for you.

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