Middletown Vacations from $366
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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.
The Latest Middletown vacation packages
Price found within the past 48 hours. Click for updated prices.
Waynebrook Inn, Est 1865
$366
per person
Oct 14 - Oct 17
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Harrisburg (MDT)
8.2/10 Very Good! (945 reviews)
I have photos if you’d like. There was a closet in our room that when you opened the door there was “construction material” . Exposed ceiling opening with ductwork exposed. Leading to attic? Was the top floor.
Ceiling tiles were water stained.
Wallpaper in bathroom peeling.
Handicap toilet near breakfast area had broken toilet seat. 1/4 of the seat was missing.
Was a real letdown!
Reviewed on Aug 23, 2026
Lancaster Arts Hotel
Stadium District
$743
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Harrisburg (MDT)
9.4/10 Exceptional! (1,010 reviews)
Nice hotel with an excellent restaurant in a great downtown location. However, our room was overdue for an update. Mattress was a bit saggy, bathroom grout was cracked and dirty, AC was noisy and TV had no streaming.
Reviewed on Aug 23, 2026
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. Savor tastings on the deck overlooking vineyards and enjoy live music events.
Middletown & Hummelstown Railroad
8.0/10 (18 reviews)
This vintage railroad 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
$119
per adult
Middletown Hotel Deals
Comfort Inn & Suites – Harrisburg Airport – Hershey South
1589 W Harrisburg Pike Middletown PA
Fully refundable
$113 nightly
$125 total
Aug 30 - Aug 31
Total with taxes and fees
9.2/10 Wonderful! (1,016 reviews)
"Nice large room very clean"
Reviewed on Aug 23, 2026
Holiday Inn Harrisburg East by IHG
815 South Eisenhower Boulevard Middletown PA
Fully refundable
$93 nightly
$103 total
Aug 30 - Aug 31
Total with taxes and fees
Days Inn by Wyndham Hershey
350 W Chocolate Ave Hershey PA
Fully refundableReserve now, pay when you stay
$127 nightly
$141 total
Sep 7 - Sep 8
Total with taxes and fees
8.6/10 Excellent! (2,076 reviews)
"Stayed for a night to attend a concert at Hersheypark Stadium - solid hotel but a bit overpriced for the quality of the hotel. Convenient location to get to the concert and the front desk staff was very helpful though!"
Reviewed on Aug 23, 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.
Find the Best Middletown Vacation Packages
Middletown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Harrisburg Intl. Airport (MDT) |
Population | 9,100 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Hersheypark, Hershey Theatre and Troegs Brewing Company |
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Frequently asked questions
How much does a Middletown vacation package cost?
Offering excellent value package deals from $366 on Expedia, you'll be thrilled with how little a vacation 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 score a cheap Middletown vacation package, consider visiting in November, December and January. You'll generally find better prices on hotels and airfares during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Middletown?
Dedicate around 2 days for your Middletown vacation if you want to enjoy everything that makes this place special. Wander around popular neighborhoods, including Highspire and Bressler-Enhaut-Oberlin. Then check out major sights such as Middletown & Hummelstown Railroad and Penn State Harrisburg. With a well-organized itinerary, you'll be kept busy with room for some rest time too. Want to travel outside of Middletown? Consider fitting in an excursion or two.
Is it worth booking a vacation package to Middletown?
Well known for its history and home to leading attractions like Middletown & Hummelstown Railroad, a Middletown vacation is sure to impress. Another top sight to visit? Don't miss Doc's Family Fun Center.
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 vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and stays individually. Better still, you can customize 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 vacation package to Middletown?
If you have your Middletown vacation 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 get away: Check your diary and get packing. Your favorite time of year and the activities on offer will also help you decide when to vacation in Middletown.
- Budget wisely: In addition to the cost of your hotel, you'll need to consider other expenses. These include transportation, flights and food. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Middletown.
- Organize your Middletown escape with Expedia's trip planning tool: Search for and book accommodations and things to do all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Middletown together.
- Decide how long to go away for: Now that you know more about Middletown, you can figure out the right length of your break. Put together a draft itinerary and allocate enough time for all the things you want to do.
- Bundle your airfare and accommodations: Once you've nailed down your trip dates and duration, book the ideal Middletown vacation package for you.
- Add on experiences and excursions: Take 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 trying to find activities once you arrive.
Does Expedia offer Book Now, Pay Later Middletown vacation packages?
Jet off on your dream escape to Middletown with help from Expedia's Book Now, Pay Later vacations. No need to save up or wait for your next paycheck — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily budget for your trip and snag great deals while they last.
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- Hershey Theatre
- Hersheypark
- Middletown & Hummelstown Railroad
- Hershey's Chocolate World
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- Bube's Brewery
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- Penn State Harrisburg
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- Deer Valley Golf Course
- Hershey Gardens
- Zooamerica
- Kohl Memorial Park
- The Vineyard and Brewery at Hershey
- Spring Gate Vineyard
- Pennsylvania Vacations
- Founder's Hall at the Milton Hershey School
- Koziar's Christmas Village
- Pennsylvania State Capitol
- Hershey Vacations
- Doc's Family Fun Center
- State Museum of Pennsylvania
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.