Middletown Vacations from $550

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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.
Eisenhower Hotel & Conference Center

Eisenhower Hotel & Conference Center

3 out of 5
Price was $681, price is now $550 per person
$550
per person
Sep 3 - Sep 7
found 18 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Harrisburg (MDT)
6.8/10 (1,002 reviews)
It was nice the rooms were updated and clean

Reviewed on Jun 15, 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 $860, price is now $624 per person
$624
per person
Aug 6 - Aug 11
found 9 hours ago
Roundtrip flight included
New York (NYC) to Harrisburg (MDT)
8.8/10 Excellent! (542 reviews)
Fantastic resort! Highly recommend. Lots of amenities and the staff was incredibly kind. The food at the Eagle & Owl was delicious. Locations was perfect. The landscaping was also beautiful.

Reviewed on Jun 15, 2026

The Lodges at Gettysburg

The Lodges at Gettysburg

3 out of 5
Price was $868, price is now $646 per person
$646
per person
Sep 3 - Sep 7
found 18 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Harrisburg (MDT)
9.4/10 Exceptional! (1,009 reviews)
This was a wonderful place to stay. It was very comfortable and situated in a very beautiful area. Great value for its price.A few amenities we would’ve liked to have had include perhaps a small breakfast lunch and even having the bar open in the afternoon all seven days of the week.

Reviewed on Jun 12, 2026

Inn at Cemetery Hill

Inn at Cemetery Hill

2 out of 5
Gettysburg Historic District
Price was $866, price is now $653 per person
$653
per person
Sep 3 - Sep 7
found 18 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Harrisburg (MDT)
9.4/10 Exceptional! (1,037 reviews)
Great location, thankful for free parking, and helpful staff.

Reviewed on Jun 15, 2026

Wyndham Gettysburg Hotel & Conference Center

Wyndham Gettysburg Hotel & Conference Center

3.5 out of 5
Price was $845, price is now $664 per person
$664
per person
Sep 3 - Sep 7
found 18 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Harrisburg (MDT)
8.8/10 Excellent! (1,584 reviews)
Everything as described. Room was cleaned and the overall property and location was great. Close to downtown area to local restaurants and shops.

Reviewed on Jun 15, 2026

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Stay near popular Middletown attractions

The Vineyard and Brewery at Hershey

4.1/5 (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.
See properties

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
$93 nightly
The price is $103 total per night from Jul 5 to Jul 6
$103 total
Jul 5 - Jul 6
Total with taxes and fees
7.4/10 Good! (1,007 reviews)
"Pictures online are very deceiving. Pool was not open. Bar was lacking. Our room was not cleaned, we had to go to the front desk for clean towels and a bag for trash."

Reviewed on Jun 14, 2026

Holiday Inn Harrisburg East by IHG
Days Inn by Wyndham Hershey

Days Inn by Wyndham Hershey

2.5 out of 5
350 W Chocolate Ave Hershey PA
$151 nightly
The price is $168 total per night from Jun 17 to Jun 18
$168 total
Jun 17 - Jun 18
Total with taxes and fees
8.6/10 Excellent! (1,964 reviews)
"Bed was comfy. Place was clean. It was nice!"

Reviewed on Jun 15, 2026

Days Inn by Wyndham Hershey
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 17 to Jun 18
$76 total
Jun 17 - Jun 18
Total with taxes and fees
7.2/10 Good! (2,278 reviews)
"First, to get to the hotel you had to drive through/around abandoned/neglected properties. The room had dirty stained pillowcases, a broken lamp and power strips plugged into power strips. The fridge was in a clothing closet. The bathroom was infested with ants and the fan did not work or there was ..."

Reviewed on Jun 15, 2026

Ramada by Wyndham Harrisburg/Hershey Area
See all 1,057 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 $550 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.

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