
Middletown Vacations from ¥211,193
Book a Hotel + Flight or Car together to unlock savings
Photo by Vincent Ramundo
- Plan, book, travel with confidence
- Better togetherSave up to ¥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.

Newburgh Inn
Price was ¥216,299, price is now ¥211,193 per person
¥211,193
per person
Mar 11 - Mar 17
found 4 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Newburgh (SWF)
5.4/10 (111 reviews)
I have wondering things to say about my enjoying everything regards my choice to book & stay at The Red Roof Roof Hotel & Suites in Newburgh, NY.
The staff is outstanding. They all are professional & friendly. It’s a safe, clean hotel. The bonuses at this particular hotel include gorgeous sunrises & sunsets. Overlooking a lake that faces east.
I highly recommend choosing The Red Roof when in this area.
Sincerely,
Jeannine C
Reviewed on Nov 10, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Price was ¥269,014, price is now ¥242,722 per person
¥242,722
per person
Mar 11 - Mar 17
found 4 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Newburgh (SWF)
9.4/10 Exceptional! (906 reviews)
The room is very spacious and clean, plus the young woman that checked me in was personable and professional.
Reviewed on Dec 25, 2025



Holiday Inn Express Hotel & Suites Chester by IHG
Price was ¥258,412, price is now ¥248,804 per person
¥248,804
per person
Mar 11 - Mar 17
found 4 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Newburgh (SWF)
8.4/10 Very Good! (1,003 reviews)
Very clean room - great stay would stay again!
Reviewed on Dec 27, 2025
Find the Best Middletown Vacation Packages
Middletown Hotel Deals

Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Fully refundable
The price is ¥16,263 per night from Jan 18 to Jan 19
¥16,263
¥19,210 total
Jan 18 - Jan 19, 2026
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
Wonderful stay rate’s very reasonable room very clean and quiet. Staff was very inviting and helpful. Looking forward to staying again went in the Middletown New York area
Reviewed on Dec 22, 2025

Hampton Inn by Hilton Middletown
20 Crystal Run Crossing Middletown NY
Fully refundableReserve now, pay when you stay
The price is ¥11,312 per night from Jan 4 to Jan 5
¥11,312
¥13,363 total
Jan 4 - Jan 5, 2026
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
Friendly staff. Room was tidy and clean. Breakfast area was clean & organized. The only issue was that the thermostat wasn't working, and front desk said they will check on that when we check out.
Reviewed on Dec 26, 2025

Courtyard by Marriott Middletown Goshen
24 Crystal Run Xing Middletown NY
Fully refundableReserve now, pay when you stay
The price is ¥15,172 per night from Jan 11 to Jan 12
¥15,172
¥17,923 total
Jan 11 - Jan 12, 2026
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
Hotel was clean and in good condition. Convenient location. On;y provided one regular and one decaf coffee pouch even though two people in room. Did not have staff in breakfast area to take order. Had to have front desk call out to public area. Annoying to have to wait for person to take order at ...
Reviewed on Dec 21, 2025
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.
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.
