Chester, NY

Travel Guide

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
The price is SAR 435 per night from May 8 to May 9
SAR 435
SAR 492 total
includes taxes & fees
8 May - 9 May
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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 April 2025

Holiday Inn Express Hotel & Suites Chester by IHG
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
The price is SAR 411 per night from May 6 to May 7
SAR 411
SAR 465 total
includes taxes & fees
6 May - 7 May
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,004 reviews)
"An amazing experience"

Reviewed on 1 May 2025

HYATT house Fishkill/Poughkeepsie
La Quinta Inn & Suites by Wyndham Middletown
La Quinta Inn & Suites by Wyndham Middletown
2.5 out of 5
551 Route 211 E, Middletown, NY
The price is SAR 475 per night from May 11 to May 12
SAR 475
SAR 561 total
includes taxes & fees
11 May - 12 May
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (687 reviews)
"The receptionist is an absolute pro: friendly and eager to help improve our stay. She should be running the NYC Four Seasons... Anyway, location is great with Starbucks across the lot. Hotel is quiet and extremely clean. It looks brand new both inside and out. We'll keep coming again and again."

Reviewed on 29 April 2025

La Quinta Inn & Suites by Wyndham Middletown
See all 981 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.
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
Stay at this vacation home in Fishkill. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions SplashDown Beach and Van Wyck Homestead Museum ...
9.6/10 Exceptional! (6 reviews)
Cozy and comfortable
"The house was beautiful, cozy, and very comfortable. We only stayed for one night, and since it was raining, we didn’t get a chance to explore the surrounding area. One cool feature was the projector and screen in the living room — it definitely made our trip more fun and memorable. The only minor ..."

Reviewed on 13 April 2025

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Cozy Cabin with Sauna & Firepit!
Cozy Cabin with Sauna & Firepit!
Monroe
Stay at this vacation home in Monroe. Enjoy air conditioning. Popular attractions Woodbury Common Premium Outlets and Palaia Vineyards Winery are located ...
9.4/10 Exceptional! (24 reviews)
Charming Cabin
"We enjoyed our short stay at this comfy little cabin! It’s cozy and has a “lived-in” feel—definitely a bit worn, but still charming and functional. The outdoor space is the real highlight: the deck, fire pit, and sauna were perfect for relaxing. It’s also in a great location near wineries and some ..."

Reviewed on 1 May 2025

Cozy Cabin with Sauna & Firepit!
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View
Newburgh
Book a stay at this family-friendly vacation home in Newburgh. Enjoy free WiFi, a water park, and a fitness center. Our guests praise the helpful staff in our ...
10/10 Exceptional! (285 reviews)
Beautiful spot and a fantastic host
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"

Reviewed on 2 May 2025

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View
See all 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.

Popular places to visit

The Rock Sports Complex

4/5(4 reviews)

Explore the great outdoors at The Rock Sports Complex, a lovely green space in Chester. While you're in the area, find time to visit its shops.

The Rock Sports Complex

Castle Fun Center

4/5(7 reviews)

You can take time to visit Castle Fun Center during your travels to Chester. While you're in the area, find time to visit its shops.

Castle Fun Center

Museum Village

5/5(1 review)

You can spend an afternoon exploring the galleries in Museum Village during your trip to Chester. While in this family-friendly area, find time to visit its shops.

Museum Village