Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 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

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
2 Bryle Place Chester NY
Fully refundable
The price is NZ$205 per night from 7 May to 8 May
NZ$205
7 May - 8 May
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
The hotel is very clean and well maintained. The staff is very friendly and helpful. The water pressure was low in the shower.

Reviewed on 4 May 2026

Holiday Inn Express Hotel & Suites Chester by IHG
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
The price is NZ$248 per night from 28 May to 29 May
NZ$248
28 May - 29 May
includes taxes & fees
8.8/10 Excellent! (1,017 reviews)
Room clean, modern, airy, same as bathroom. Breakfast very good with hot/cold items. Parking great. Great location too. Staff was wonderful and very helpful with questions I had.

Reviewed on 6 May 2026

Sleep Inn & Suites Middletown - Goshen
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is NZ$192 per night from 1 June to 2 June
NZ$192
1 June - 2 June
includes taxes & fees
8/10 Very Good! (80 reviews)
The staff were very accommodating and attentive to my requests of staying in a quieter floor with a later check-in. The room was extremely clean and bigger than I expected, with the AC working perfectly (as I like to sleep in a cold room). Breakfast was no-frills (bagels, cereal, juice, etc) but ...

Reviewed on 30 Apr 2026

Spark by Hilton Fishkill
See all 1,081 properties in Chester
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.

Museum Village

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.