Middletown Vacations from $273

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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.
DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
Save 100% on your flight
Price was $461, price is now $273 per person
$273
per person
Dec 5 - Dec 10
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,006 reviews)
Rooms were amazing - staff was helpful, and was able to add this additional day to the other stay for the full weekend- and the staff provided the ability for us to keep our room the same.

Reviewed on Oct 1, 2025

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Save 100% on your flight
Price was $560, price is now $313 per person
$313
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
9.4/10 Exceptional! (1,010 reviews)
The property was beautiful. The staff was amazing and the area is so easy to get around plenty of dining and entertainment options.

Reviewed on Oct 2, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $608, price is now $346 per person
$346
per person
Dec 5 - Dec 10
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.2/10 Very Good! (1,002 reviews)
This was a great option with the hotel on the college campus for convenience to visit with grandkids but also walking distance for great restaurants. Very clean, friendly and accommodating staff. Highly recommend it.

Reviewed on Sep 11, 2025

Pier 5 Hotel Baltimore

Pier 5 Hotel Baltimore

3.5 out of 5
Inner Harbor
Save 100% on your flight
Price was $495, price is now $306 per person
$306
per person
Dec 5 - Dec 8
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (741 reviews)
Full array of places to eat and drink. Right next to the Pier 6 concert venue. Harbor is beautiful.

Reviewed on Oct 1, 2025

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
Save 100% on your flight
Price was $852, price is now $531 per person
$531
per person
Nov 6 - Nov 9
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,008 reviews)
Room smelled musty. Couldn’t catch my breath overnight. I contacted the manager. He said he would have someone check. Never heard back.

Reviewed on Oct 2, 2025

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Discover the most popular places to visit in Middletown

Maryland National Golf Club

Enjoy a round of golf in Middletown at Maryland National Golf Club. Discover the coffeehouses and its festivals while you're in the area.

Maryland National Golf Club

Orchid Cellar Winery

You can enjoy a tasting or tour at Orchid Cellar Winery during your travels to Middletown. Discover the area's festivals, or seek out its golf courses.

Orchid Cellar Winery

Middletown Hotel Deals

Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

3 out of 5
5579 Spectrum Dr, Frederick, MD
Fully refundable
$88 nightly
The price is $98 total per night from Oct 26 to Oct 27
$98 total
Oct 26 - Oct 27
Total with taxes and fees
8.2/10 Very Good! (1,133 reviews)
"Clean room, good accommodations and parking, convient location"

Reviewed on Sep 26, 2025

Country Inn & Suites by Radisson, Frederick, MD
Quality Inn

Quality Inn

2.5 out of 5
25 Union St, Harpers Ferry, WV
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $99 total per night from Oct 28 to Oct 29
$99 total
Oct 28 - Oct 29
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
All the basics done well
"Nice, comfortable stay in Harpers Ferry. They did the essentials well, like cleanliness, comfortable bed, and water pressure. A pretty good breakfast too! A little surprised at the price (a tad higher than most QIs) but not a lot of hotel options in Harpers Ferry, and still less than a BnB"

Reviewed on Oct 2, 2025

Quality Inn
Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town

2.5 out of 5
4328 William L Wilson Fwy, Harpers Ferry, WV
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $103 total per night from Nov 3 to Nov 4
$103 total
Nov 3 - Nov 4
Total with taxes and fees
7.8/10 Good! (1,036 reviews)
"Staff was amazing. The whole building needs to be renovated"

Reviewed on Oct 1, 2025

Clarion Inn Harpers Ferry - Charles Town
See all 800 properties in Middletown
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.

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 $273 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.