Chester Holidays

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Top hotels in Chester

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 3.368.960 ₫ per night from 2 Jul to 3 Jul
3.368.960 ₫
4.148.032 ₫ total
2 Jul - 3 Jul
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"The rooms were large, staff was friendly and complimentary breakfast had a large variety of food."

Reviewed on 24 Jun 2026

Holiday Inn Express Hotel & Suites Chester by IHG
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
The price is 4.448.080 ₫ per night from 30 Jun to 1 Jul
4.448.080 ₫
5.476.699 ₫ total
30 Jun - 1 Jul
includes taxes & fees
8.4/10 Very good! (1,004 reviews)
"everything was amazing , my husband and I really enjoyed our time there"

Reviewed on 26 Jun 2026

Overlook Lodge at Bear Mountain
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 3.225.516 ₫ per night from 29 Jun to 30 Jun
3.225.516 ₫
3.810.346 ₫ total
29 Jun - 30 Jun
includes taxes & fees
8.8/10 Excellent! (1,042 reviews)
"Clean room loved my stay with my family the kids enjoy the pool a lot of things close by to do too…"

Reviewed on 25 Jun 2026

Sleep Inn & Suites Middletown - Goshen
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.

Stay near popular Chester attractions

The Rock Sports Complex

8.0/5 (18 reviews)
This dedicated sports venue hosts baseball and softball tournaments on well-maintained turf fields. Bring portable chairs and sun protection to enjoy the games in comfort at this local athletic hub.
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