Middletown Vacations from $287

Book a Hotel + Flight or Car together to unlock savings

Photo by Doug Kerr
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to $580 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, 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.
Element Arundel Mills BWI Airport

Element Arundel Mills BWI Airport

3 out of 5
Save 100% on your flight
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
Overnight stay close to the airport. Clean hotel with good reception and parking space. Drive to Baltimore downtown is around 15 mins and 50 mins to DC

Reviewed on Jul 24, 2024

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
Save 100% on your flight
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.8/10 Excellent! (2,178 reviews)
Great location for easy walking down to Georgetown shopping without having to deal with looking for a park. Would definitely stay again!

Reviewed on Sep 26, 2024

Ulysses, an Ash Hotel

Ulysses, an Ash Hotel

4 out of 5
Midtown
Save 100% on your flight
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9/10 Wonderful! (507 reviews)
Lovely facility, great and helpful staff.

Reviewed on Sep 25, 2024

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
Fells Point
Save 100% on your flight
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9.4/10 Exceptional! (960 reviews)
A great atmosphere, really awesome bar and restaurant, beautiful rooms. The pool was a bit cold but beautiful area.

Reviewed on Aug 25, 2024

Viceroy Washington DC

Viceroy Washington DC

4.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Dec 2 - Dec 6
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Washington (DCA)
9.2/10 Wonderful! (873 reviews)
Parking needs to free or at a lower cost

Reviewed on Sep 22, 2024

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

Ready to book your vacation to Middletown?

 

Choose your dates

Middletown Hotel Deals

Countryside Cabin with Mountain Views near Surreybrooke Gardens
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Middletown
10/10 Exceptional! (74 reviews)
Very nice property
"Great location! easy access to C&O trail, historic sites, State Parks and supplies and resturants."

Reviewed on Sep 12, 2024

Get rates
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
The price is $200 per night from Sep 30 to Oct 1
$200
includes taxes & fees
$189 per night
Sep 30 - Oct 1
Overnight in Cozy Cabin
"Such a quaint little cabin! It had the rustic feel, but was located in town, so very convenient. The stairs to the upstairs bedroom were a bit tricky, but also added to the charm of the cabin. Overall, very impressive!"

Reviewed on Aug 27, 2024

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
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
The price is $93 per night from Oct 6 to Oct 7
$93
includes taxes & fees
$84 per night
Oct 6 - Oct 7
8.4/10 Very Good! (1,000 reviews)
Great stay
"Very friendly staff; clean, comfortable room; hot breakfast was good. I definitely will stay again next year."

Reviewed on Sep 22, 2024

Country Inn & Suites by Radisson, Frederick, MD
See all 683 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Middletown vacation package cost?
You can snap up a vacation package to this destination from $287 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?
Start your search for a Middletown package deal by entering your travel dates and destination under our “Packages” tab. Then add a few filters, like “Property type” and “Amenities,” to fine-tune the results to your exact needs. You can also sort by “Package discount” and browse offers that come with irresistible savings. If you don’t find the perfect Middletown package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Middletown adventure underway.
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’re planning an impromptu Middletown adventure, check out our last-minute deals that can be booked up to one week before you go. Don’t want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Middletown?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Middletown.
  2. Plan your budget wisely: Besides the price of your stay, you should consider other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that could crop up during your trip to Middletown.
  3. Discover Middletown using Expedia’s trip planning tool: Gain insights into the most popular attractions and best stays for your trip to Middletown. You can also save your favorite locations, collaborate with your group and manage your plans in one place.
  4. Decide your trip length: Consider how much time you’d like to spend discovering Middletown. Plan your itinerary so you can get to all the activities and attractions you’re interested in without rushing.
  5. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that’s left is to choose a Middletown vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Have a look at our travel guide to find some exciting things to do in Middletown. Book tickets or make reservations in advance to save time and skip the hassle of looking for activities once you arrive.

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.

Discover the most popular places to visit in Middletown

Image for Maryland National Golf Club

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
Image for Orchid Cellar Winery

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
Image for Willow Oaks Craft Cider and Wine

Willow Oaks Craft Cider and Wine

You can enjoy a tasting or tour at Willow Oaks Craft Cider and Wine during your travels to Middletown. Amble around the area's riverfront or experience its entertainment venues.

Willow Oaks Craft Cider and Wine
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.