Middletown Vacations from $318
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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.
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
$473
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,253 reviews)
Very good breakfast menu - good variety, reasonably priced.
Opaline restaurant food was excellent - octopus, Lasagna, pappardelle. So convenient to just eat in hotel after traveling all day. Patio dining was very relaxing.
Perfect location. Taxis always available.
Reviewed on Aug 30, 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.
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.
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.
Middletown Hotel Deals
Country Inn & Suites by Radisson, Frederick, MD
5579 Spectrum Dr Frederick MD
Fully refundable
$85 nightly
$94 total
Sep 20 - Sep 21
Total with taxes and fees
8.2/10 Very Good! (1,361 reviews)
"Breakfast was not very good. Room was clean and good for what we needed."
Reviewed on Aug 30, 2026
The Plaza Inn & Suites
931 Dual Highway, Building A Hagerstown MD
Fully refundableReserve now, pay when you stay
$66 nightly
$74 total
Sep 4 - Sep 5
Total with taxes and fees
6/10 (609 reviews)
"If you need a place to get in and out and don’t expect much, it is OK"
Reviewed on Aug 30, 2026
Best Western Historic Frederick
420 Prospect Blvd Frederick MD
Fully refundableReserve now, pay when you stay
$77 nightly
$85 total
Sep 8 - Sep 9
Total with taxes and fees
8/10 Very Good! (1,006 reviews)
"The room was very damp, the humidity in the was wasn’t good. I turned the heat on to dry out the room. There were no rooms left for me switch rooms on stay."
Reviewed on Aug 30, 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 $318 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.
