Middletown Vacation Packages
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Your Middletown Vacation
Say farewell to the worries of planning and hello to a Middletown vacation package. With everything organized before you go, you can focus on discovering this city, starting with Downtown Harrisburg, which is great for shopping, cafes and families. Any trip to Middletown needs a well-planned itinerary. Fill yours with major attractions like Penn State Harrisburg, The Vineyard and Brewery at Hershey and Saturdays Market. Expedia can help you escape the everyday. Tailor your vacation to Middletown to suit your style of travel, whatever that may be.
Top Middletown Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Wyndham Gettysburg Hotel & Conference Center
CA $850
per person
Oct 30 - Nov 2
found 2 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Harrisburg (MDT)
9/10 Wonderful! (1,647 reviews)
This was a clean hotel with comfortable accomodations, but is in need of some updating. One elevator was out of order throughout our stay and a second failed midway through the weekend, leaving only one working during a busy convention.
The hallways are in need of updates due to peeling/damaged wallpaper.
While not crucial to the average guest, both the hotel and it's staff could benefit from updated safety equipment and preparedness training, as a medical emergency was observed during the stay.
Reviewed on Aug 11, 2026
Ready to book your vacation to Middletown?
Middletown Hotel Deals
Comfort Inn & Suites – Harrisburg Airport – Hershey South
1589 W Harrisburg Pike Middletown PA
Fully refundable
CA $150
CA $167 total
Aug 30 - Aug 31
includes taxes & fees
Holiday Inn Harrisburg East by IHG
815 South Eisenhower Boulevard Middletown PA
Fully refundable
CA $123
CA $136 total
Aug 30 - Aug 31
includes taxes & fees
7.2/10 Good! (1,000 reviews)
"It’s fine for a one-night stay, but I wouldn’t recommend it for a longer visit (3+ days). The shower door was broken, and the toilet barely flushed. Housekeeping “made” the bed while we were out for the day, but it didn’t look like any real effort was made—the pillows were just tossed around, and ..."
Reviewed on Aug 10, 2026
Days Inn by Wyndham Hershey
350 W Chocolate Ave Hershey PA
CA $175
CA $197 total
Sep 9 - Sep 10
includes taxes & fees
8.6/10 Excellent! (2,034 reviews)
"If you are going to Hershey for personal or business this is the place to stay. Most convenient location to everything, clean hotel with helpful staff from check in till check out. You can shop price but for best all around value, this is the place to stay at the Sweetest Place on earth!"
Reviewed on Aug 11, 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)
You can take time to visit The Vineyard and Brewery at Hershey during your travels to Middletown. Discover the local chocolate shops and entertainment choices in this family-friendly area.
Middletown & Hummelstown Railroad
8.0/10 (18 reviews)
Take the family on an outing to Middletown & Hummelstown Railroad during your trip to Middletown. Attend a sporting event or simply enjoy the local chocolate shops while you're in the area.
Doc's Family Fun Center
7.4/10 (11 reviews)
You can enjoy the entertainment at Doc's Family Fun Center during your trip to Middletown. Experience the great live music or attend a sporting event in this family-friendly area.
What to do in Middletown
Rise and Dine Food Tour in Vintage Style Trolley
CA $167
per adult
Frequently asked questions
How much does a Middletown vacation package cost?
You'll find cheap prices from CA $687 on Expedia for your Middletown getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Middletown costs.
What are the cheapest months to go to Middletown?
December, January and February are the best times to search for cheap Middletown vacation packages. Opting to travel in less busy periods means you'll typically find lower prices on flights and hotels.
How many days is enough for Middletown?
To get the most out of your Middletown vacation, we recommend booking for 2 days. Split your time between discovering Middletown & Hummelstown Railroad, Hershey Area Playhouse and other leading sights, as well as exploring neighbourhoods like Highspire and Bressler-Enhaut-Oberlin. If you've got some time to spare, add a day trip to your Middletown vacation itinerary.
Is it worth booking a vacation package to Middletown?
From top attractions such as Middletown & Hummelstown Railroad and Doc's Family Fun Centre to its excellent history, a Middletown vacation delivers big on experiences. With so much to do and see, it's time to find out for yourself why Middletown is such a good vacation destination.
How to find the best Middletown package deals?
Use Expedia's filter tool to find some terrific 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're looking to save, plan your trip for midweek, or browse for Middletown package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Middletown vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and stays individually. Better still, you can personalize your Middletown escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Middletown?
If you've got your Middletown travel dates confirmed, book as early as you can to score some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Middletown?
- Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Middletown.
- Budget wisely: As well as the cost of your hotel, you should consider other expenses. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that may come up during your trip to Middletown.
- Decide how many days away: Start by compiling a list of the activities and sights you want to experience in Middletown. Then, estimate how long you'll need for each, including any travel time.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Middletown vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
