
Chester Vacations from ¥197,107
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The Latest Chester Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport
Price was ¥213,574, price is now ¥197,107 per person
¥197,107
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Newburgh (SWF)
5.4/10 (1,016 reviews)
Staff was very Good in every way
Reviewed on Nov 1, 2025

Sleep Inn & Suites Middletown - Goshen
Price was ¥235,745, price is now ¥209,930 per person
¥209,930
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Newburgh (SWF)
8.4/10 Very Good! (1,031 reviews)
Enjoyed my stay the rooms were very clean and nice
Reviewed on Nov 5, 2025

The Crossroads Hotel, Newburgh
Price was ¥272,315, price is now ¥252,997 per person
¥252,997
per person
Dec 28 - Jan 3
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Newburgh (SWF)
7.2/10 Good! (617 reviews)
Yes, every thing was clean. Staff was very friendly. My only complaint was , that a handicap room should have a raised toilet in those rooms.
Reviewed on Oct 31, 2025

Cottage Suites
Price was ¥250,174, price is now ¥233,464 per person
¥233,464
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Newburgh (SWF)
5/10 (8 reviews)
The owner did not reply to my outreach and provided no means of contact. It was very hard to find the building at night as it is situated in a multi-street intersection. There was also no guidance on parking. I ended up booking a different place to stay overnight.
Reviewed on Sep 1, 2025

Holiday Inn Express & Suites Montgomery by IHG
Price was ¥224,426, price is now ¥213,274 per person
¥213,274
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Newburgh (SWF)
8.8/10 Excellent! (770 reviews)
The fire alarm went off at 7am and the lady at the front desk was a bit rude. My friends had there handicapped grandparents staying there and no one thought to help them get evacuated. The staff had an attitude when they were trying to go to their room until my friends spoke up and said they had people in a wheelchair. And only then did they offer to help. The situation could have been handled with more professionalism despite it being 7am
Reviewed on Oct 26, 2025
Find the Best Chester Vacation Packages
Chester Hotel Deals

Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place, Chester, NY
Fully refundable
The price is ¥12,280 per night from Nov 9 to Nov 10
¥12,280
¥14,506 total
Nov 9 - Nov 10
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
The staff was helpful and when they weren’t helping they were cleaning. The rooms are spotless.
Reviewed on Nov 3, 2025

Sonesta Simply Suites Nanuet
20 Overlook Blvd, Nanuet, NY
Fully refundableReserve now, pay when you stay
The price is ¥16,578 per night from Nov 18 to Nov 19
¥16,578
¥19,292 total
Nov 18 - Nov 19
includes taxes & fees
8.2/10 Very Good! (1,062 reviews)
Everything was great
Reviewed on Nov 2, 2025

The Crossroads Hotel, Newburgh
5 Lakeside Rd, Newburgh, NY
The price is ¥15,059 per night from Nov 10 to Nov 11
¥15,059
¥17,788 total
Nov 10 - Nov 11
includes taxes & fees
7.2/10 Good! (656 reviews)
Yes, every thing was clean. Staff was very friendly. My only complaint was , that a handicap room should have a raised toilet in those rooms.
Reviewed on Oct 31, 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.
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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.
