Middletown Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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
Middletown Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Rachael's Inner Harbor Boutique Inn
Ridgely's Delight
S$1,130
per person
23 Oct - 26 Oct
found 1 day ago
Return flight included
Salt Lake City (SLC) to Baltimore (BWI)
8.8/10 Excellent! (11 reviews)
We had a great time. Was in town for a baseball game and the location was great. The room was clean and very large. We will most likely be back next time the PHILLIES are in town.
Reviewed on 11 Aug, 2026
The Inn at Henderson's Wharf, an Ascend Collection Hotel
Fells Point
S$1,075
per person
23 Oct - 26 Oct
found 1 day ago
Return flight included
Salt Lake City (SLC) to Baltimore (BWI)
9.2/10 Wonderful! (835 reviews)
The evening I checked in, your front desk man: Eric was friendly and extremely helpful. The room was spotless and the beds were amazingly comfortable. I will recommend this hotel to friends and family. 2 thumbs up, get adventurous fun!
Reviewed on 13 Aug, 2026
Top hotels in Middletown
Country Inn & Suites by Radisson, Hagerstown, MD
17612 Valley Mall Rd Hagerstown MD
S$148
13 Sept - 14 Sept
includes taxes & fees
Country Inn & Suites by Radisson, Frederick, MD
5579 Spectrum Dr Frederick MD
Fully refundable
S$115
13 Sept - 14 Sept
includes taxes & fees
8.2/10 Very good! (1,361 reviews)
"Everything was great. Would stay again."
Reviewed on 15 Aug, 2026
The Plaza Inn & Suites
931 Dual Highway, Building A Hagerstown MD
Fully refundableReserve now, pay when you stay
S$90
18 Aug - 19 Aug
includes taxes & fees
6/10 (600 reviews)
"This hotel was very run down, dirty room grab bar in shower came off. Loud yelling. Towels were very clean sheets stained staff was polite and helpful I would not recommend this hotel to anybody, especially not loan travelers as was stated in the description that it was highly rated by loan travelers ..."
Reviewed on 17 Aug, 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.
Stay near popular Middletown attractions
Maryland National Golf Club
Designed by Arthur Hills, this par-71 course features dramatic elevation changes and views of the Catoctin Mountains. Enjoy the challenging fairways and relax at the full-service clubhouse after your round.
Willow Oaks Craft Cider and Wine
Maryland's first certified organic farm offers barrel-aged craft ciders and port-style wines from its 35-acre orchard. Savour a tasting on the deck overlooking the apple trees while browsing local art in the gallery.
Orchid Cellar Winery
9.0/10 (2 reviews)
Orchid Cellar crafts diverse meads in a hand-built log cabin tasting room with mountain views. Enjoy a flight on the wrap-around deck while watching resident bees and chickens or roasting s'mores by the fire pit.
Frequently asked questions
How much does a Middletown holiday package cost?
You can snap up a holiday package to this destination from S$1,000 on Expedia. However, how much your holiday 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?
The off-season is the best time to head to Middletown if you're on a budget. Another tip for finding cheap Middletown holiday packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Middletown?
With a well-organised schedule, you can easily visit the most popular Middletown sights in a handful of days. But if you'd like to discover hidden gems or go on day trips, consider booking your Middletown holiday 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 holiday package as soon as possible.
Is it cheaper to book a Middletown holiday as a package?
Expedia holiday 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 personalised Middletown holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Middletown?
If you've got your Middletown holiday 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.
How to plan a trip to Middletown?
- Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Middletown.
- Plan your budget wisely: In addition to the price of your stay, you'll need to factor in other expenses too. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that could arise during your trip to Middletown.
- Work out your trip length: Consider how much time you'd like to spend discovering Middletown. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
- Combine your airfare and accommodation: Once you've nailed down your travel dates and duration, lock in the right Middletown holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
