Find hotels in Chester, NY from 1.740.486 ₫

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5 Dec - 6 Dec
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6 Dec - 7 Dec
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5 Dec - 7 Dec
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12 Dec - 14 Dec

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Top 10 Chester hotels and places to stay

Exterior
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 star property
Chester
8.6 out of 10, Excellent, (1002)
"Great for a quick stay 👍"
United States
Jerry
The price is 2.088.583 ₫
2.467.139 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Hotel & Suites Chester by IHG
Superior Double Room, Ensuite (Primrose) | Miscellaneous
The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast

2.0 star property
Chester
9.2 out of 10, Wonderful, (233)
"Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY."
United States
Erek
The price is 5.669.765 ₫
6.413.955 ₫ total
includes taxes & fees
8 Dec - 9 Dec
The Dominion House Bed & Breakfast
Exterior
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

2.5 star property
Middletown
8.6 out of 10, Excellent, (1002)
"Room was clean and staff was great!"
United States
Annemarie
The price is 1.983.099 ₫
2.342.535 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn by Hilton Middletown
Outdoor pool
LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

3.0 star property
Goshen
8.8 out of 10, Excellent, (32)
"We loved everything from the staff to the stay "
United States
Arnassia
The price is 5.019.456 ₫
9.133.655 ₫ total
includes taxes & fees
22 Dec - 23 Dec
LEGOLAND Hotel NEW York
Lobby
Quality Inn near Mountain Creek

Quality Inn near Mountain Creek

2.5 star property
Vernon
7.6 out of 10, Good, (971)
"Nice hotel. Close to golf,"
United States
Joseph
The price is 2.215.691 ₫
2.539.736 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Quality Inn near Mountain Creek
Lobby
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4.0 star property
Nanuet
8.8 out of 10, Excellent, (1002)
"Very clean very beautiful very good hospitality would stay again"
United States
Bobby
The price is 2.573.477 ₫
2.994.883 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Hotel Nanuet
Room, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board
Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

2.5 star property
Monroe
9.4 out of 10, Exceptional, (1001)
"Clean and easy check in. "
United States
chris
The price is 2.133.941 ₫
2.414.020 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Sleep Inn & Suites Monroe - Woodbury
Buffet
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

2.5 star property
Fishkill
8.4 out of 10, Very good, (1004)
"I had a very nice stay"
United States
Mischelle
The price is 2.505.245 ₫
2.834.060 ₫ total
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
Room, 2 Queen Beds, Non Smoking | In-room safe, desk, iron/ironing board, free cots/infant beds
Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro

2.0 star property
Wurtsboro
7.6 out of 10, Good, (590)
"I love "
United States
Niralkumar
The price is 2.129.620 ₫
2.406.471 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Days Inn by Wyndham Wurtsboro
Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1003)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
The price is 3.138.149 ₫
3.550.064 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Overlook Lodge at Bear Mountain
View from property
Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

2.5 star property
Goshen
8.8 out of 10, Excellent, (1002)
"This place is fantastic from the staff to the rooms. Very clean. Will definitely stay here again."
United States
Linda
The price is 2.452.503 ₫
3.019.644 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Fairfield Inn & Suites by Marriott Goshen Middletown
Exterior
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3.0 star property
Middletown
9.4 out of 10, Exceptional, (928)
"great staff, clean rooms, nice breakfast .. overall a pleasant & safe atmosphere !"
United States
Emerson
The price is 2.712.463 ₫
3.204.096 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Lobby
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1005)
"Very clean rooms, nice courteous staff continental breakfast was great."
United States
KATHERINE
The price is 2.721.487 ₫
3.350.830 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn Harriman Woodbury
Interior
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 star property
Suffern
8.8 out of 10, Excellent, (1004)
"The staff, the cleanliness of the room, the food and overall it was a good stay. Will stay again."
United States
Cynthia
The price is 2.742.584 ₫
3.191.684 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Crowne Plaza Suffern - Mahwah by IHG
Free daily continental breakfast
Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

2.5 star property
Fishkill
8.8 out of 10, Excellent, (1003)
"Very nice overnight stay."
United States
Jannifer
The price is 2.353.612 ₫
2.662.523 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Quality Inn & Suites Fishkill South near I-84
Free daily buffet breakfast
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

2.5 star property
Fishkill
9.2 out of 10, Wonderful, (1000)
"Easy check in, very friendly staff. Clean place!!"
United States
Elline
The price is 2.801.919 ₫
3.169.672 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Comfort Suites Fishkill near Interstate 84
BBQ/picnic Area
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 star property
Middletown
8.6 out of 10, Excellent, (1001)
"Friendly staff, clean room and great breakfast "
United States
Janet
The price is 2.443.273 ₫
2.886.116 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Sleep Inn & Suites Middletown - Goshen
Exterior
Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

2.5 star property
Montgomery
8.8 out of 10, Excellent, (794)
"Room was clean a d spacious. Staff courteous and helpful."
United States
David
The price is 2.373.390 ₫
2.684.896 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Montgomery by IHG
Lobby
Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill

3.0 star property
Fishkill
8.6 out of 10, Excellent, (1002)
"It was a great place to stay "
United States
Amanda
The price is 2.416.375 ₫
2.733.525 ₫ total
includes taxes & fees
12 Dec - 13 Dec
Hilton Garden Inn Fishkill
Reception
Tru by Hilton Middletown

Tru by Hilton Middletown

2.5 star property
Middletown
8.6 out of 10, Excellent, (952)
"Would stay again "
United States
Susan
The price is 2.357.040 ₫
2.784.254 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Tru by Hilton Middletown
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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Stay near popular Chester attractions

The Rock Sports Complex

4.0/5 (10 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.
See properties

Museum Village

4.5/5 (4 reviews)
Step back in time at Museum Village, where costumed interpreters bring 19th-century rural American life to vivid reality. Explore historic buildings and watch traditional craftspeople demonstrate forgotten skills.
See properties

Learn more about Chester

Lace up your hiking boots and hit the trails at Goosepond Mountain State Park for stunning views. After working up an appetite, head to Castle Fun Centre for go-karts, mini-golf, and arcade games.

See all hotels in Chester
Black dirt region farm Chester New York

Top Chester Hotel Reviews

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

10/10 Excellent
"Great staff and great stay"
William 1-night trip
Posted 3 weeks ago
The Crossroads Hotel, Newburgh

More cheap stays in Chester

Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

20 Overlook Blvd Nanuet NY
The price is 2.913.996 ₫ per night from 8 Dec to 9 Dec
2.913.996 ₫
3.391.161 ₫ total
8 Dec - 9 Dec
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)

Hotels in Chester with star rating

Frequently asked questions

What's the seasonal weather like in Chester?
The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Chester are January, February, March and April, with each month seeing an average of 16 cm of snowfall.

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