Middletown Vacations from $457
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $400 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
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.
Kellogg Conference Hotel at Gallaudet University
Northeast
Save 100% on your flight
Price was $651, price is now $457 per person
$457
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,007 reviews)
It was so nice, and it is a college campus, so it is really safe. Pet-friendly and good breakfast. Parking is way too expensive. No need to charge $50 a night when there is plenty of parking.
Reviewed on Apr 4, 2026
Club Wyndham National Harbor
Save 100% on your flight
Price was $1,518, price is now $1,038 per person
$1,038
per person
Jun 16 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (480 reviews)
Everything was top notch would differently stay again
Reviewed on Mar 9, 2026
Historic Inns of Annapolis
Historic District
Save 100% on your flight
Price was $1,028, price is now $710 per person
$710
per person
May 27 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Baltimore (BWI)
9/10 Wonderful! (1,875 reviews)
We used Vallet parking and Inn transportation to other parts of town. It would be convenient to have a small breakfast at the hotel.
Reviewed on Apr 24, 2026
The Westin DC Downtown
Downtown Washington D.C.
Save 100% on your flight
Price was $692, price is now $480 per person
$480
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,009 reviews)
I would highly recommend this hotel to anyone. The staff are nice and helpful when we had questions. The staff at Root &Vine when we order pizza's to take back to our room. The sercurity guards in the lobby would always say hi and ask how you are doing. The room was amazing and we enjoyed the view from our room.
Reviewed on Apr 10, 2026
Lyle Washington D.C.
Northwest
Save 100% on your flight
Price was $1,031, price is now $719 per person
$719
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
9.4/10 Exceptional! (1,676 reviews)
From the second we pulled up to the valet the staff was fantastic. Front desk had everything we needed. Bartender was awesome. Room beautiful. Would definitely book there again.
Reviewed on Apr 25, 2026
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.
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.
Middletown Hotel Deals
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown MD
$175 nightly
The price is $186 total per night from Apr 27 to Apr 28
$186 total
Apr 27 - Apr 28
Total with taxes and fees
9.6/10 Exceptional! (114 reviews)
Really cool historic cabin! Close to the Middletown main street. Me and my wife cooked in the cabin just about every night, pots plates and silverware stocked. Gas fireplace was powerful and heated the whole cabin easily on cold nights. Great antiques items scattered around the cabin. Was very quiet ...
Reviewed on Apr 13, 2026
Country Inn & Suites by Radisson, Frederick, MD
5579 Spectrum Dr Frederick MD
Fully refundable
$87 nightly
The price is $97 total per night from May 25 to May 26
$97 total
May 25 - May 26
Total with taxes and fees
8.2/10 Very Good! (1,291 reviews)
Breakfast was good, had good parking spot. But AC kept going on and off by itself. other than that everything is perfect.
Reviewed on Apr 21, 2026
Quality Inn Harpers Ferry - Charles Town
25 Union St Harpers Ferry WV
Fully refundable
$89 nightly
The price is $99 total per night from May 25 to May 26
$99 total
May 25 - May 26
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
Breakfast was really good, great selection. Parking was plentiful and spacious.
Reviewed on Apr 23, 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 |
More vacations you might like
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
