Middletown Vacations from $362

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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.
Inn at Cemetery Hill

Inn at Cemetery Hill

2 out of 5
Gettysburg Historic District
Save 100% on your flight
Price was $523, price is now $362 per person
$362
per person
Aug 1 - Aug 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Harrisburg (MDT)
9.4/10 Exceptional! (1,008 reviews)
Location & breakfast was great

Reviewed on May 31, 2026

Parkview Inn & Suites Lancaster

Parkview Inn & Suites Lancaster

3 out of 5
Dutch Countryside
Price was $1,276, price is now $862 per person
$862
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Harrisburg (MDT)
9.4/10 Exceptional! (1,211 reviews)
The property well displayed every imarginary annemities for the guess. It was well thought out and done. The only set back was the carpet throught out . It cause my wife to cough and sneeze alot. The carpet needs to be removed from throught out, and let the tile reigh all over. Then I will give the location an A plus, instead of the A minus I am assesing now.

Reviewed on Jun 1, 2026

Liberty Mountain Lodging by Vail Resorts

Liberty Mountain Lodging by Vail Resorts

2.5 out of 5
Save 100% on your flight
Price was $634, price is now $448 per person
$448
per person
Aug 1 - Aug 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Harrisburg (MDT)
8.8/10 Excellent! (534 reviews)
Visiting family. Convenient and tasty Resturant/bar. Enjoyed our stay.

Reviewed on May 30, 2026

Conestoga Manor

Conestoga Manor

2 out of 5
Price was $1,394, price is now $997 per person
$997
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Harrisburg (MDT)
No reviews
Wyndham Gettysburg Hotel & Conference Center

Wyndham Gettysburg Hotel & Conference Center

3.5 out of 5
Save 100% on your flight
Price was $520, price is now $383 per person
$383
per person
Aug 1 - Aug 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Harrisburg (MDT)
8.8/10 Excellent! (1,560 reviews)
Very nice hotel. Rooms were clean and beds were comfortable. Recommend this stay.

Reviewed on Jun 1, 2026

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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

Hershey Trolley Crawl and Evening Food Tour on a Vintage Trolley

Hershey Trolley Crawl and Evening Food Tour on a Vintage Trolley

$50
per adult
Hershey Trolley Crawl and Evening Food Tour on a Vintage Trolley
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
$106 nightly
The price is $118 total per night from Jun 30 to Jul 1
$118 total
Jun 30 - Jul 1
Total with taxes and fees
7.4/10 Good! (998 reviews)
"The staff were super friendly and helpful. However upon arrival we arrived pretty late at 2a.m we went to our room and noticed the bathroom were gross , pubes in our shower and just disgusting. Then ourselves and our children were woken up multiple times throughout the night by the ac system which ..."

Reviewed on May 31, 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
$69 nightly
The price is $76 total per night from Jun 7 to Jun 8
$76 total
Jun 7 - Jun 8
Total with taxes and fees
7.2/10 Good! (2,232 reviews)
"Staff is nice and friendy"

Reviewed on May 31, 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
$150 nightly
The price is $167 total per night from Jun 7 to Jun 8
$167 total
Jun 7 - Jun 8
Total with taxes and fees
8.6/10 Excellent! (1,956 reviews)
"Everyone was nice and kind and knowledgeable. The breakfast was excellent. The cleaning staff did an excellent job."

Reviewed on May 31, 2026

Days Inn by Wyndham Hershey
See all 1,062 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

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Frequently asked questions

How much does a Middletown vacation package cost?
Offering excellent value package deals from $362 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.