Middletown Vacations from $226

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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.
Baltimore executive Furnished rentals

Baltimore executive Furnished rentals

4 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $332, price is now $226 per person
$226
per person
Mar 18 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8/10 Very Good! (2 reviews)
The Normandy Hotel

The Normandy Hotel

3 out of 5
Northwest
Save 100% on your flight
Price was $413, price is now $255 per person
$255
per person
Mar 10 - Mar 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.4/10 Very Good! (1,002 reviews)
Rooms were very clean and staff was pleasant

Reviewed on Jan 22, 2026

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Save 100% on your flight
Price was $476, price is now $304 per person
$304
per person
Feb 25 - Mar 2
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,001 reviews)
Everything was perfect

Reviewed on Jan 15, 2026

Rosewood Washington, D.C.

Rosewood Washington, D.C.

5 out of 5
Northwest
Save 100% on your flight
Price was $2,934, price is now $1,953 per person
$1,953
per person
Mar 12 - Mar 15
found 21 hours ago
Roundtrip flight included
Miami (MIA) to Washington (DCA)
9.2/10 Wonderful! (194 reviews)
Wonderful staff, clean and comfortable room.

Reviewed on Jan 7, 2026

Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Price was $345, price is now $234 per person
$234
per person
Mar 28 - Mar 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8/10 Very Good! (1,178 reviews)
I appreciate the staff front desk was the most supportive and supportive and great personality and security

Reviewed on Jan 24, 2026

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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

Countryside Cabin with Mountain Views near Surreybrooke Gardens

Countryside Cabin with Mountain Views near Surreybrooke Gardens

Middletown MD
10/10 Exceptional! (132 reviews)
Fantastic cabin for a weekend getaway! Very nice setup, incredibly gracious host, and beautiful view! Can’t wait to book again next year!

Reviewed on Jan 4, 2026

Get rates
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Hampton Inn & Suites Frederick-Fort Detrick

Hampton Inn & Suites Frederick-Fort Detrick

2.5 out of 5
1565 Opossumtown Pike Frederick MD
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $89 total per night from Feb 1 to Feb 2
$89 total
Feb 1 - Feb 2
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
Room was clean & staff was courteous.

Reviewed on Jan 19, 2026

Hampton Inn & Suites Frederick-Fort Detrick
Hilton Garden Inn Frederick

Hilton Garden Inn Frederick

3 out of 5
7226 Corporate Ct Frederick MD
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $106 total per night from Jan 29 to Jan 30
$106 total
Jan 29 - Jan 30
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
Good location, clean room, nice lobby, and restaurant on site! All staff were welcoming. A special thanks to our waiter JR at the restaurant who was so friendly. The breakfast was excellent! Will definitely stay here again!

Reviewed on Jan 19, 2026

Hilton Garden Inn Frederick
See all 805 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.

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 $226 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.