Chester Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to NZ$616 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
Chester Holiday
Our pick of the best Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place, Chester, NY
The price is NZ$206 per night from 4 May to 5 May
NZ$206
includes taxes & fees
4 May - 5 May
8.4/10 Very Good! (1,001 reviews)
"Room is big and clean, bed is comfortable. About a 5-min drive away from Legoland. Would definitely stay here again if given the opportunity."
Reviewed on 29 Apr. 2025
Overlook Lodge at Bear Mountain
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Fully refundableReserve now, pay when you stay
The price is NZ$255 per night from 11 May to 12 May
NZ$255
includes taxes & fees
11 May - 12 May
8.2/10 Very Good! (1,001 reviews)
"The staff, room and property were lovely. The view from the porch? Spectacular !!!"
Reviewed on 28 Apr. 2025
La Quinta Inn & Suites by Wyndham Middletown
551 Route 211 E, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is NZ$252 per night from 5 May to 6 May
NZ$252
includes taxes & fees
5 May - 6 May
9.2/10 Wonderful! (685 reviews)
Clean, friendly service, lots of parking
"Just an overnight stop but this place was perfect! It was quiet, clean, Elora at the front desk was lovely and it was reasonably priced."
Reviewed on 28 Apr. 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.
Discover the most popular places to visit in Chester
Museum Village
You can spend an afternoon studying the exhibits at Museum Village in Chester. While in this family-friendly area, find time to visit its shops.
More holiday ideas
Expedia's Latest Trends
Hotels
Activities
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.