Middletown Vacations from $309
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Your Middletown Vacation
Say goodbye to the stress of planning and hello to a Middletown vacation package. With everything organized before you leave, you can focus on discovering this city, starting with Downtown Frederick, which is great for cafes, bars and pubs and culture. Make your trip to Middletown even more fulfilling by going sightseeing. Musket Ridge Golf Course, Maryland National Golf Club and Washington Monument State Park are among the popular attractions you'll want to explore. Stop daydreaming and start doing. Browse the wide range of options on Expedia today and finally put your Middletown vacation plans in motion!
The Latest Middletown vacation packages
Price found within the past 48 hours. Click for updated prices.
citizenM Washington DC Georgetown
Northwest
$309
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (166 reviews)
Staff was helpful and place was clean, but there was a leak in my room under the shower. Rooms are really space efficient (small) and modern.
Reviewed on Oct 14, 2026
The Darcy Hotel
Downtown Washington D.C.
$343
per person
Nov 19 - Nov 23
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (1,716 reviews)
Front desk staff was rude and seemed too busy talking on the phone or staying in the back office to actually help. Everything else about the property was great.
Reviewed on Oct 14, 2026
Stay near popular Middletown attractions
Maryland National Golf Club
Designed by Arthur Hills, this par-71 course features dramatic elevation changes and views of the Catoctin Mountains. Enjoy the challenging fairways and relax at the full-service clubhouse after your round.
Orchid Cellar Winery
9.0/10 (2 reviews)
Orchid Cellar crafts diverse meads in a hand-built log cabin tasting room with mountain views. Enjoy a flight on the wrap-around deck while watching resident bees and chickens or roasting s'mores by the fire pit.
Willow Oaks Craft Cider and Wine
Maryland's first certified organic farm offers barrel-aged craft ciders and port-style wines from its 35-acre orchard. Savor a tasting on the deck overlooking the apple trees while browsing local art in the gallery.
Middletown Hotel Deals
Country Inn & Suites by Radisson, Hagerstown, MD
17612 Valley Mall Rd Hagerstown MD
Fully refundable
$84 nightly
$94 total
Nov 8 - Nov 9
Total with taxes and fees
8.6/10 Excellent! (1,336 reviews)
"Great stay!"
Reviewed on Oct 15, 2026
Best Western Historic Frederick
420 Prospect Blvd Frederick MD
Fully refundableReserve now, pay when you stay
$77 nightly
$86 total
Oct 25 - Oct 26
Total with taxes and fees
Quality Inn Harpers Ferry - Charles Town
25 Union St Harpers Ferry WV
Fully refundable
$90 nightly
$101 total
Oct 28 - Oct 29
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
"Nice room for the price. Very good breakfast."
Reviewed on Oct 15, 2026
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 Middletown Vacation Packages
Middletown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Hagerstown Regional Airport (HGR) |
Population | 4,500 |
Max Temp Winter | 40ºF |
Max Temp Summer | 85ºF |
Top Sights | Orchid Cellar Winery, Musket Ridge Golf Course and Maryland National Golf Club |
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Frequently asked questions
How much does a Middletown vacation package cost?
You can snap up a vacation package to this destination from $309 on Expedia. However, how much your vacation to Middletown costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Middletown?
You're likely to find lower rates and better availability in September, October and December. Explore our cheap Middletown vacation packages and you could land some excellent off-season deals.
How many days is enough for Middletown?
With a well-organized schedule, you can easily hit the main Middletown sights in a few days. But if you want to discover lesser-known spots or take day trips, think about booking your Middletown vacation for longer.
How to find the best Middletown package deals?
Use Expedia's handy filters to help you find some great Middletown package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Middletown package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Middletown vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component individually. And you'll still get the flexibility to create a personalized Middletown vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Middletown?
If you've got your Middletown vacation dates confirmed, book as soon as you can to grab some incredible deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Middletown vacation packages?
If you're like us, you love discovering new places but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Middletown trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
