Middletown Holidays
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- Better togetherSave up to S$1,300 when you book a flight and hotel together*
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Top hotels in Middletown
Comfort Inn & Suites – Harrisburg Airport – Hershey South
1589 W Harrisburg Pike Middletown PA
Fully refundable
S$152
30 Aug - 31 Aug
includes taxes & fees
Holiday Inn Harrisburg East by IHG
815 South Eisenhower Boulevard Middletown PA
Fully refundable
S$129
13 Sept - 14 Sept
includes taxes & fees
Days Inn by Wyndham Hershey
350 W Chocolate Ave Hershey PA
Fully refundableReserve now, pay when you stay
S$181
8 Sept - 9 Sept
includes taxes & fees
8.6/10 Excellent! (2,043 reviews)
"Nice family stay with good breakfast. Room was clean and spacious."
Reviewed on 15 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
The Vineyard and Brewery at Hershey
8.2/10 (22 reviews)
Pennsylvania's first combined winery and brewery offers 20+ handcrafted wines and 10 craft beers in one charming location. Savour tastings on the deck overlooking vineyards and enjoy live music events.
Middletown & Hummelstown Railroad
8.0/10 (18 reviews)
This vintage railway journey winds through Pennsylvania's scenic landscapes aboard 1920s coaches. Experience narrated history along the Swatara Creek while passing century-old limekilns and Union Canal remnants.
Doc's Family Fun Center
7.4/10 (11 reviews)
This classic roller rink has been a family entertainment staple since 1939, offering nostalgic fun on wheels. Glide across the well-maintained skating floor before enjoying treats at the Rock n Roll Malt Shop.
What to do in Middletown
Night Fever A Signature Hershey Area Evening Food Tour
S$154
per adult
Frequently asked questions
How much does a Middletown holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Middletown costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Middletown?
If you'd like to snag a cheap Middletown holiday package, consider planning a trip in December, January and February. You're likely to find lower prices on airfares and hotels during these months — ideal for a budget-friendly break.
How many days is enough for Middletown?
We suggest planning a Middletown holiday for around 2 days. This gives you plenty of time to visit key attractions such as Middletown & Hummelstown Railroad and Doc's Family Fun Centre, and check out neighbourhoods like Highspire and Bressler-Enhaut-Oberlin. You could even make time for a day trip outside of Middletown.
Is it worth booking a holiday package to Middletown?
Well known for its history and home to popular attractions like Middletown & Hummelstown Railroad, a Middletown holiday is sure to impress. Another top sight to check out? Don't miss Doc's Family Fun Centre.
How to find the best Middletown package deals?
Begin your search for a Middletown package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Middletown package deal right away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Middletown adventure off to a flying start.
Is it cheaper to book a Middletown holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging flights and stays individually. Better still, you can customise your Middletown getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Middletown?
If you have your Middletown holiday dates finalized, book as soon as you can to bag some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Middletown?
- Choose when to go: Check your schedule and get your bags packed. Your favourite season and the activities available will also help you decide when to visit Middletown.
- Budget wisely: As well as the cost of your stay, you should consider other expenses. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Middletown.
- Decide how long to go for: Now that you know more about Middletown, you can figure out the right length of your holiday. Put together a draft plan and give yourself enough time to get through everything on your must-do list.
- Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a personalised Middletown holiday package.
* 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.
