Middletown Vacations from ￥318,903

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Middletown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Kixby

Kixby

4 out of 5
Manhattan
Price was ￥394,310, price is now ￥318,903 per person
￥318,903
per person
Sep 30 - Oct 5
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9.4/10 Exceptional! (1,940 reviews)

The Fifty Sonesta Hotel New York

The Fifty Sonesta Hotel New York

4 out of 5
Manhattan
Price was ￥577,478, price is now ￥409,671 per person
￥409,671
per person
Aug 31 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.6/10 Excellent! (1,528 reviews)

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Price was ￥715,302, price is now ￥520,356 per person
￥520,356
per person
Sep 19 - Sep 26
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
8/10 Very Good! (2,471 reviews)
Convenient location and helpful staff.

Reviewed on Jul 19, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was ￥487,759, price is now ￥356,152 per person
￥356,152
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (3,130 reviews)
Nice staff; decent breakfast buffet; for being in the Times Square are of NYC, I think it is a good value.

Reviewed on Jul 19, 2026

Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Price was ￥414,018, price is now ￥338,732 per person
￥338,732
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (4,331 reviews)

Find the Best Middletown Vacation Packages

Middletown Hotel Deals

DoubleTree by Hilton Hotel Newark Airport

DoubleTree by Hilton Hotel Newark Airport

4 out of 5
128 Frontage Rd Newark NJ
Fully refundable
The price is ￥17,653 per night from Aug 9 to Aug 10
￥17,653
￥21,297 total
Aug 9 - Aug 10
includes taxes & fees
DoubleTree by Hilton Hotel Newark Airport
DoubleTree by Hilton New York Downtown

DoubleTree by Hilton New York Downtown

4 out of 5
8 Stone St New York NY
Fully refundableReserve now, pay when you stay
The price is ￥21,380 per night from Aug 16 to Aug 17
￥21,380
￥25,669 total
Aug 16 - Aug 17
includes taxes & fees
8.4/10 Very Good! (4,029 reviews)
"Our stay was mostly fine overall. This is an extremely busy property, and the lobby was consistently crowded. The biggest frustration was the elevators. They were very difficult to get, so because we were on the fifth floor, we ended up taking the stairs almost every time we went up or down. The ..."

Reviewed on Jul 19, 2026

DoubleTree by Hilton New York Downtown
Holiday Inn Newark International Airport by IHG

Holiday Inn Newark International Airport by IHG

3.5 out of 5
160 Frontage Road Newark NJ
Fully refundable
The price is ￥15,612 per night from Aug 16 to Aug 17
￥15,612
￥18,460 total
Aug 16 - Aug 17
includes taxes & fees
8.2/10 Very Good! (3,120 reviews)
"I liked that the hotel was quite large with an in house restaurant & coffee shop. However the room was half updated. The beds were updated but the dresser and I guess what was considered the closet was old & peeling. So disgusting . Some other old wood decor surrounding a miror on the wall was h-i-d-e-o-u-s. ..."

Reviewed on Jul 19, 2026

Holiday Inn Newark International Airport by IHG
See all 3,296 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.

Stay near popular Middletown attractions

Deep Cut Gardens

8.6/10 (18 reviews)
This 54-acre horticultural haven features roses, Japanese gardens, and century-old bonsai. Wander through the display greenhouse year-round or join the Garden Safari Backpack program.
See properties

Frequently asked questions

How much does a Middletown vacation package cost?
You'll find cheap prices from ￥318,903 on Expedia for your Middletown break. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Middletown costs.
What are the cheapest months to go to Middletown?
If you're looking to score a cheap Middletown vacation package, consider visiting in February, March and November. You'll typically find lower rates on hotels and flights during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Middletown?
Generally, a handful of days is enough to tick off the main sights during your Middletown vacation. However, if you prefer to have some time to kick back or take day tours, think about extending your itinerary.
How to find the best Middletown package deals?
Use Expedia's filter tool to help you find some fabulous Middletown package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Middletown package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Middletown vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still enjoy the freedom to create a customized Middletown vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Middletown?
Secure fantastic discounts by reserving your flights early with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Middletown vacation.
How to plan a trip to Middletown?

  1. Pick your dates: What you plan to do in Middletown and your preferred season can help you decide when to get away.
  2. Set a budget: Factor in expenses like transportation, flights and meals when calculating how much to set aside for your trip to Middletown. Then, choose a property that fits your budget, whether that's an affordable option or a swankier getaway.
  3. Decide your trip length: Think about how much time you'd like to spend exploring Middletown. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a personalized Middletown vacation package.

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