Middletown Vacations from $180

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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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8/10 Very Good! (792 reviews)
Hotel was just okay. For a non-smoking hotel, the smell of cigarette smoke was still present in the rooms and hallways. The breakfast was minimal and not what I expected given prior reviews.

Reviewed on Jul 3, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.2/10 Very Good! (1,005 reviews)
The good thing is it is on Gallaudet's property.

Reviewed on Jun 23, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
10/10 Exceptional! (3 reviews)
Very difficult to pull up and take advantage of valet parking. Otherwise, everything was AMAZING!

Reviewed on Jun 29, 2025

YOTEL Washington DC

YOTEL Washington DC

4 out of 5
Northwest
Save 100% on your flight
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.4/10 Very Good! (1,950 reviews)
Very clean and comfortable rooms. I love the led lights. The rooftop pool was beautiful and the food/drinks were great!

Reviewed on Jul 4, 2025

Holiday Inn Columbia East-Jessup by IHG

Holiday Inn Columbia East-Jessup by IHG

3 out of 5
Save 100% on your flight
per person
Aug 13 - Aug 19
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (998 reviews)
They had a pool! The rooms are bigger than most for a good price

Reviewed on Jul 1, 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
$81 nightly
The price is $90 total per night from Jul 7 to Jul 8
$90 total
Jul 7 - Jul 8
Total includes taxes and fees
8.2/10 Very Good! (1,032 reviews)
"I recently stayed at the Country Inn & Suites in Frederick, MD, and overall had a great experience. The location is fantastic—close to plenty of restaurants and attractions, making it really convenient for both business and leisure trips. The staff here were incredibly friendly and helpful, from ..."

Reviewed on Jul 1, 2025

Country Inn & Suites by Radisson, Frederick, MD
Hilton Garden Inn Frederick
Hilton Garden Inn Frederick
3 out of 5
7226 Corporate Ct, Frederick, MD
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $117 total per night from Jul 7 to Jul 8
$117 total
Jul 7 - Jul 8
Total includes taxes and fees
8.8/10 Excellent! (1,001 reviews)
"Room need more lighting."

Reviewed on Jul 2, 2025

Hilton Garden Inn Frederick
Super 8 by Wyndham Hagerstown/Halfway Area
Super 8 by Wyndham Hagerstown/Halfway Area
2 out of 5
16805 Blake Rd, I 70 & I 81, Hagerstown, MD
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $77 total per night from Jul 13 to Jul 14
$77 total
Jul 13 - Jul 14
Total includes taxes and fees
8.4/10 Very Good! (1,013 reviews)
"The hotel is clean and lovely. The room was clean amd refreshing and my daughter and myself felt at home. The staff was kind and helpful. Its a good thing the management keeps out local people. Which keeps the hotel cleaner and more luxurious. Because the area has a trailer trucks rest stops all ..."

Reviewed on Jun 28, 2025

Super 8 by Wyndham Hagerstown/Halfway Area
See all 774 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 $180 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.