Middletown Holidays from £1,076
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Your Middletown Holiday
Say farewell to the worries of planning and hello to a Middletown holiday package. With everything organised 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 holiday to Middletown to suit your style of travel, whatever that may be.
Top Middletown Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Red Caboose Motel
£1,346
per person
1 Nov - 8 Nov
found 1 day ago
Return direct flight included
London (LHR) to Harrisburg (MDT)
9.4/10 Exceptional! (1,074 reviews)
I stayed at the Red Caboose motel as a child. 40 years later, it is still a really neat and unusual place to stay. A lot of remodeling has been done on the cabooses in that time, but the amenities are great. Staff was very attentive and friendly -- you know, the kind of staff that enjoys their job and make it show every time. Our caboose had four bunks, a double bed, TV, A/C, electric baseboard heat, a hot shower, nice bathroom sink, fridge/freezer, microwave. We enjoyed our stay and look forward to maybe returning next year.
Reviewed on 29 Sept 2026
Middletown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Harrisburg Intl. Airport (MDT) |
Population | 9,100 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Hersheypark, Hershey Theatre and Troegs Brewing Company |
Top hotels in Middletown
Holiday Inn Harrisburg East by IHG
815 South Eisenhower Boulevard Middletown PA
Fully refundable
£63
29 Oct - 30 Oct
includes taxes & fees
Ramada by Wyndham Harrisburg/Hershey Area
300 N Mountain Rd Harrisburg PA
Fully refundableReserve now, pay when you stay
£50
12 Oct - 13 Oct
includes taxes & fees
7.4/10 Good! (2,493 reviews)
"This hotel is a 10/10, the staff is so helpful and friendly, and the amenities were put to great use. My boyfriend and I booked the king size bedroom with the hot tub and we were not disappointed at all. We really enjoyed the hot tub and would love to book again soon. Also, a great price to pay with ..."
Reviewed on 30 Sept 2026
Days Inn by Wyndham Hershey
350 W Chocolate Ave Hershey PA
Fully refundableReserve now, pay when you stay
£82
12 Oct - 13 Oct
includes taxes & fees
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.
Frequently asked questions
How much does a Middletown travel package cost?
Our Middletown travel packages, which start at just £1,076, are an awesome way to save loads of cash. Handpick your preferred flights, hotels and rental cars to create a customized trip.
If I'm not able to travel, can I cancel my Middletown travel package?
Don't worry if you're rethinking your Middletown travel package — it's possible to change or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We understand life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that occurs. When you're ready to make changes, we'll be here to help.
How do I get a cheap travel package to Middletown?
Booking a Middletown travel package with Expedia is a smart way to save. We have access to more than 550 airlines and 1,000,000 hotel options around the world. With such an amazing range to pick from, you'll have no worries pulling together your ideal trip.
Does Expedia offer Book Now, Pay Later Middletown holidays?
We certainly do. Expedia has joined forces with online lender Klarna to help you easily pay for your trip in instalments. Simply choose the payment plan that works for you during the checkout process and take away the stress of budgeting for your trip. Be sure to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your travel buck. Take a look at our flexible payment options below:
- Pay monthly holidays: If paying bite-sized amounts each month sounds right for you, Klarna can help. Paying in convenient monthly instalments will make that dream holiday possible.
- Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then check out this Book Now, Pay Later option with Klarna.
- Low deposit holidays: When you want to jump on an amazing deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you secure your getaway.
Where should I stay in Middletown?
A getaway to Middletown wouldn't be complete without stopping by Penn State Harrisburg, The Vineyard and Brewery at Hershey and Middletown & Hummelstown Railroad. Spend your nights near these tourist attractions and make sightseeing a breeze.
What are the top hotels in Middletown?
Many savvy travellers choose to stay at Fairfield Inn & Suites by Marriott Harrisburg International Airport in Highspire. If this is your first trip to Middletown, you'll receive a warm welcome here.
How far in advance should I book my Middletown holiday?
To score rock-bottom prices, book early. Airlines typically advertise flight tickets, along with some of the lowest fares, up to 12 months ahead of time. Hotels, car rental and activities should also be booked early so you can have the pick of the bunch. If you're in need of a last-minute getaway to Middletown, there are always lots of great deals to be had on Expedia. Book your escape today!
What does an Expedia Middletown travel package include?
Hotels, car rentals and flights — we bring you the very best bargains. All you have to do is pick and choose your favourite combination. After you've made your booking, you can add on the fun stuff like activities and tours. Our travel packages make it easy to create an amazing Middletown trip.
What should I know before booking a Middletown travel package?
Locking in all the parts of your trip together is a terrific way to save. Combine your flights, car rentals and hotels into a convenient package. But you're not limited to hotels. Expedia has all sorts of properties, including holiday rentals like beachfront villas and spacious residences. The list goes on!
Can I choose my airline with a Middletown Expedia travel package?
Definitely. Expedia has more than 550 partner airlines to select from across the world. With all that choice at your fingertips, finding the perfect carrier to whisk you away to Middletown will be a cinch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
