Middleburg Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Middleburg Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Clear Spring by IHG
CA $1,261
per person
Nov 30 - Dec 5
found 1 day ago
Roundtrip flight included
Edmonton (YEA) to Hagerstown (HGR)
8.6/10 Excellent! (1,004 reviews)
Room was clean and staff was good. Breakfast was awesome and gym also was good. Good for family stay.
Reviewed on Oct 22, 2026
Ready to book your vacation to Middleburg?
Middleburg Hotel Deals
Wyndham Gettysburg Hotel & Conference Center
95 Presidential Cir Gettysburg PA
Fully refundableReserve now, pay when you stay
CA $132
CA $147 total
Nov 22 - Nov 23
includes taxes & fees
9/10 Wonderful! (1,656 reviews)
"Room clear signs of wear and could use updates."
Reviewed on Oct 23, 2026
Hotel Gettysburg
One Lincoln Square Gettysburg PA
Fully refundableReserve now, pay when you stay
CA $175
CA $194 total
Nov 22 - Nov 23
includes taxes & fees
9.4/10 Exceptional! (1,376 reviews)
"Room was clean and bed was comfortable. Quiet for being right downtown. Always a plus when there is a Starbucks close by too."
Reviewed on Oct 22, 2026
Inn at Cemetery Hill
613 Baltimore St Gettysburg PA
Fully refundableReserve now, pay when you stay
CA $129
CA $143 total
Nov 16 - Nov 17
includes taxes & fees
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?
Offering excellent value package deals from CA $1,261 on Expedia, you'll be surprised at how little a vacation to Middleburg costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Middleburg?
You can generally find reduced prices and better availability in January, February and March. Take a look at our cheap Middleburg vacation packages and you could score some excellent off-season deals.
How many days is enough for Middleburg?
With a well-organized travel plan, you can easily hit the main Middleburg attractions in a few days. But if you'd like to discover lesser-known spots or go on day trips, think about booking your Middleburg vacation for longer.
How to find the best Middleburg package deals?
Start your search for a Middleburg package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Middleburg package deal straight away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Middleburg adventure off to a flying start.
Is it cheaper to book a Middleburg vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Middleburg vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Middleburg?
If you're planning a spontaneous Middleburg adventure, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Middleburg?
- Choose when to travel: Check your schedule and pack your bags. Your favourite season and the type of activities available will also help you decide when to visit Middleburg.
- Plan your budget wisely: As well as the cost of your stay, you'll need to consider other expenses. These include food, transportation and flights. Also, put aside a little extra for unexpected expenses that could crop up during your trip to Middleburg.
- Decide your trip length: Consider how much time you'd like to spend exploring Middleburg. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
- Bundle your accommodations and airfare: Once you've settled on your travel dates and duration, lock in the perfect Middleburg vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
