Middletown Vacation Packages

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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.

Top Middletown Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Harrisburg - Hershey Area, I-81 by IHG

Holiday Inn Harrisburg - Hershey Area, I-81 by IHG

3 out of 5
Price was CA $1,304, price is now CA $1,161 per person
CA $1,161
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Harrisburg (MDT)
7.2/10 Good! (1,001 reviews)
The carpet in the room was very old and peeling up off the floor. Pieces of the stairs were breaking off. We did not use any of the amenities. The overall structure was dilapidated. The manager was also not trustworthy. He lied multiple times about not charging me a fee; reassured me that he would take care of it, and never did. So many hotels are offering continental breakfast and this one does not. I would not recommend staying here.

Reviewed on Jul 3, 2026

Wyndham Gettysburg Hotel & Conference Center

Wyndham Gettysburg Hotel & Conference Center

3.5 out of 5
Price was CA $1,388, price is now CA $1,204 per person
CA $1,204
per person
Oct 2 - Oct 5
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Harrisburg (MDT)
8.8/10 Excellent! (1,611 reviews)

Hampton Inn & Suites Hershey Near The Park

Hampton Inn & Suites Hershey Near The Park

2.5 out of 5
Price was CA $1,431, price is now CA $1,282 per person
CA $1,282
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Harrisburg (MDT)
8.8/10 Excellent! (1,004 reviews)

Aspire Gettysburg Hotel

Aspire Gettysburg Hotel

3 out of 5
Price was CA $1,459, price is now CA $1,320 per person
CA $1,320
per person
Oct 2 - Oct 5
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Harrisburg (MDT)
7.6/10 Good! (983 reviews)

Liberty Mountain Lodging by Vail Resorts

Liberty Mountain Lodging by Vail Resorts

2.5 out of 5
Price was CA $1,340, price is now CA $1,223 per person
CA $1,223
per person
Oct 2 - Oct 5
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Harrisburg (MDT)
8.8/10 Excellent! (551 reviews)
The room and bathroom were very clean. There wasn’t a blow dryer in the room and the staff delivered one to me within 15 min. The staff members were all very friendly!

Reviewed on Jul 14, 2026

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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 CA $122 per night from Aug 2 to Aug 3
CA $122
CA $135 total
Aug 2 - Aug 3
includes taxes & fees
7.2/10 Good! (1,000 reviews)
"Clean room and friendly staff"

Reviewed on Jul 14, 2026

Holiday Inn Harrisburg East by IHG
Comfort Inn & Suites – Harrisburg Airport – Hershey South

Comfort Inn & Suites – Harrisburg Airport – Hershey South

2.5 out of 5
1589 W Harrisburg Pike Middletown PA
Fully refundable
The price is CA $151 per night from Aug 9 to Aug 10
CA $151
CA $168 total
Aug 9 - Aug 10
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Everyone at the front desk that was there for our five day. Stay was very helpful and friendly and went out of their way for us. Included breakfast in the morning. We’re very well stocked and the food was high-quality. Would certainly stay here again!"

Reviewed on Jul 13, 2026

Comfort Inn & Suites – Harrisburg Airport – Hershey South
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 CA $111 per night from Aug 2 to Aug 3
CA $111
CA $123 total
Aug 2 - Aug 3
includes taxes & fees
Ramada by Wyndham Harrisburg/Hershey Area
See all 1,065 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.
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Stay near popular Middletown attractions

The Vineyard and Brewery at Hershey

8.2/10 (22 reviews)
You can take time to visit The Vineyard and Brewery at Hershey during your travels to Middletown. Discover the local chocolate shops and great live music in this family-friendly area.
See properties

What to do in Middletown

Rise and Dine Food Tour in Vintage Style Trolley

Rise and Dine Food Tour in Vintage Style Trolley

CA $169
per adult
Rise and Dine Food Tour in Vintage Style Trolley
Hershey Trolley Food Tour Experience

Hershey Trolley Food Tour Experience

CA $169
per adult
Hershey Trolley Food Tour Experience
See all activities in Middletown

Frequently asked questions

How much does a Middletown vacation package cost?
You'll find cheap prices from CA $1,161 on Expedia for your Middletown getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Middletown costs.
What are the cheapest months to go to Middletown?
December, January and February are the best times to search for cheap Middletown vacation packages. Opting to travel in less busy periods means you'll typically find lower prices on flights and hotels.
How many days is enough for Middletown?
To get the most out of your Middletown vacation, we recommend booking for 2 days. Split your time between discovering Middletown & Hummelstown Railroad, Hershey Area Playhouse and other leading sights, as well as exploring neighbourhoods like Highspire and Bressler-Enhaut-Oberlin. If you've got some time to spare, add a day trip to your Middletown vacation itinerary.
Is it worth booking a vacation package to Middletown?
From top attractions such as Middletown & Hummelstown Railroad and Doc's Family Fun Centre to its excellent history, a Middletown vacation delivers big on experiences. With so much to do and see, it's time to find out for yourself why Middletown is such a good vacation destination.
How to find the best Middletown package deals?
Use Expedia's filter tool to find some terrific Middletown package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Middletown package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Middletown vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and stays individually. Better still, you can personalize your Middletown escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Middletown?
If you've got your Middletown travel dates confirmed, book as early as you can to score some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Middletown?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Middletown.
  2. Budget wisely: As well as the cost of your hotel, you should consider other expenses. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that may come up during your trip to Middletown.
  3. Decide how many days away: Start by compiling a list of the activities and sights you want to experience in Middletown. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Middletown vacation package.

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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.