Middleburg Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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 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 S$857 per night from 9 Jul to 10 Jul
S$857
9 Jul - 10 Jul
includes taxes & fees
9.2/10 Wonderful! (402 reviews)
"Great room, fantastic room d staff and spa"

Reviewed on 28 Jun, 2026

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 S$598 per night from 6 Jul to 7 Jul
S$598
6 Jul - 7 Jul
includes taxes & fees
9.6/10 Exceptional! (440 reviews)
"I thought it was over priced."

Reviewed on 28 Jun, 2026

The Red Fox Inn & Tavern
Hyatt Regency Dulles International Airport

Hyatt Regency Dulles International Airport

4 out of 5
2300 Dulles Corner Blvd Herndon VA
Fully refundableReserve now, pay when you stay
The price is S$188 per night from 5 Jul to 6 Jul
S$188
5 Jul - 6 Jul
includes taxes & fees
8.8/10 Excellent! (1,805 reviews)
"Awesome stay!"

Reviewed on 1 Jul, 2026

Hyatt Regency Dulles International Airport
See all 1,009 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 waterfall, a river, and a house in the background.

Glenwood Park

10.0/10 (2 reviews)
Glenwood Park becomes a premier equestrian venue hosting steeplechase races over natural hedges. Bring binoculars to the Virginia Autumn Races in October for the quintessential Middleburg horse racing experience.
See properties

What to do in Middleburg

Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

S$116
per adult
Leesburg Premium Outlets Shopping Tour
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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.