Middletown Vacations from $619

Book a Hotel + Flight or Car together to unlock savings

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.
Homewood Suites by Hilton Harrisburg-West Hershey Area

Homewood Suites by Hilton Harrisburg-West Hershey Area

3 out of 5
Price was $772, price is now $619 per person
$619
per person
Jul 2 - Jul 7
found 22 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Harrisburg (MDT)
9.2/10 Wonderful! (862 reviews)
Nothing bad or negative to say. My husband and I had a wonderful 4 day stay and enjoyed our time here. Clean rooms and halls, decent breakfasts. Very accommodating staff. Thankyou

Reviewed on May 12, 2026

Lancaster Suites

Lancaster Suites

2.5 out of 5
Dutch Countryside
Price was $979, price is now $701 per person
$701
per person
Jul 14 - Jul 21
found 15 hours ago
Roundtrip flight included
San Juan (SJU) to Harrisburg (MDT)
8.6/10 Excellent! (1,190 reviews)
We stayed two nights while visiting relatives. The hotel room was spacious and comfortable. The beds were comfortable. The breakfast was fine, offering basics. The hotel was located right off of a very busy highway and was extremely noisy in the mornings. All at all, I would recommend staying here as it was a good price point.

Reviewed on May 25, 2026

Parkview Inn & Suites Lancaster

Parkview Inn & Suites Lancaster

3 out of 5
Dutch Countryside
Price was $1,756, price is now $1,351 per person
$1,351
per person
Jul 14 - Jul 21
found 15 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Harrisburg (MDT)
9.4/10 Exceptional! (1,202 reviews)
Large rooms. Very clean and well maintained. Close to outlets and restaurants.

Reviewed on May 23, 2026

Inn at Lebanon - Hershey & Manheim area

Inn at Lebanon - Hershey & Manheim area

2.5 out of 5
Price was $1,125, price is now $926 per person
$926
per person
Jul 14 - Jul 21
found 15 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Harrisburg (MDT)
5.8/10 (441 reviews)
Cheap and served its purpose. But if you booked it for a good free breakfast save yourself. The breakfast was a joke.

Reviewed on May 21, 2026

Don't see what you're looking for?
See all available trips from Singapore to Middletown
View all trips

Discover the most popular places to visit in Middletown

Penn State Harrisburg

4/5(16 reviews)

Explore the campus of Penn State Harrisburg as part of your travels around Middletown. Discover the local chocolate shops and acclaimed theater scene in this family-friendly area.

Penn State Harrisburg

The Vineyard and Brewery at Hershey

3/5(1 review)

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.

The Vineyard and Brewery at Hershey

Middletown & Hummelstown Railroad

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.

Middletown & Hummelstown Railroad

What to do in Middletown

Rise and Dine Food Tour in Vintage Style Trolley

Rise and Dine Food Tour in Vintage Style Trolley

$119
per adult
Rise and Dine Food Tour in Vintage Style Trolley
Hershey Trolley Food Tour Experience

Hershey Trolley Food Tour Experience

$119
per adult
Hershey Trolley Food Tour Experience
See all activities in Middletown

Middletown Hotel Deals

Holiday Inn Harrisburg East by IHG

Holiday Inn Harrisburg East by IHG

3 out of 5
815 South Eisenhower Boulevard Middletown PA
Fully refundable
The price is $112 total per night from May 31 to Jun 1
$112 total
per night
May 31 - Jun 1
7.4/10 Good! (995 reviews)
"Hotel is slightly outdated, bed was comfortable, but pillows were flat. Room was a very large and spacious corner suite. Breakfast was not included so we paid $14/pp to eat sub-par hotel breakfast and the staff at breakfast was rude. There is a Wendy’s and Taco Bell within 5 min walking distance. ..."

Reviewed on May 17, 2026

Holiday Inn Harrisburg East by IHG
Ramada by Wyndham Harrisburg/Hershey Area

Ramada by Wyndham Harrisburg/Hershey Area

2.5 out of 5
300 N Mountain Rd Harrisburg PA
Fully refundableReserve now, pay when you stay
The price is $62 total per night from May 26 to May 27
$62 total
per night
May 26 - May 27
7.2/10 Good! (2,218 reviews)
"Service could've been better. Maintenance needs to have some lessons on well, Maintenance..."

Reviewed on May 24, 2026

Ramada by Wyndham Harrisburg/Hershey Area
Days Inn by Wyndham Hershey

Days Inn by Wyndham Hershey

2.5 out of 5
350 W Chocolate Ave Hershey PA
Fully refundableReserve now, pay when you stay
The price is $125 total per night from May 26 to May 27
$125 total
per night
May 26 - May 27
8.6/10 Excellent! (1,951 reviews)
"Breakfast was great. Check in was easy. Missing the park shuttle"

Reviewed on May 20, 2026

Days Inn by Wyndham Hershey
See all 1,060 properties in Middletown
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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Middletown vacation package cost?
Offering excellent value package deals from $619 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. Bundle your airfare and accommodations: Once you've nailed down your trip dates and duration, book the ideal Middletown vacation package for you.
  6. 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.