Find hotels in Chester, NY from 1.737.846 ₫

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24 Dec - 25 Dec
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25 Dec - 26 Dec
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26 Dec - 28 Dec
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2 Jan - 4 Jan

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Our top choices for Chester hotels

Superior Double Room, Ensuite (Primrose) | Miscellaneous
The Dominion House Bed & Breakfast

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 5.661.165 ₫
6.404.226 ₫ total
includes taxes & fees
30 Dec - 31 Dec
The Dominion House Bed & Breakfast
Exterior
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.4 out of 10, Very good, (1001)
"The breakfast was a hit, the place is clean and I would stay here again."
United States
elizabeth
The price is 2.501.635 ₫
2.955.057 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Express Hotel & Suites Chester by IHG
Free daily self-service breakfast
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
2.5 star property
Peekskill
9.2 out of 10, Wonderful, (1001)
"I highly recommend this hotel. "
United States
Leigh
The price is 3.212.382 ₫
3.674.161 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
Exterior
Cromwell Manor Inn

Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.4 out of 10, Exceptional, (94)
"Great stay!"
United States
Amrita
The price is 7.038.276 ₫
8.314.013 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Cromwell Manor Inn
Porch
Cold Spring Hotel

Cold Spring Hotel

Cold Spring Hotel
3.0 star property
Cold Spring
8.6 out of 10, Excellent, (153)
"We’ve been staying at Cold Spring Hotel for the last 5 years. Jimmy, the owner, makes us feel at home every time. He is friendly and very professional. We recommend Cold Spring Hotel 100%."
United States
Leonardo
Cold Spring Hotel
Standard Room, 2 Queen Beds, Accessible (ADA) | Desk, laptop workspace, blackout curtains, iron/ironing board
West Point Motel

West Point Motel

West Point Motel
2.5 star property
Highland Falls
8.6 out of 10, Excellent, (663)
"Clean room and so close to West Point!! Great experience 👍 "
United States
SHANNON
The price is 2.633.100 ₫
2.978.826 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
West Point Motel
Front of property
The Dutchess Inn and Spa at Beacon

The Dutchess Inn and Spa at Beacon

The Dutchess Inn and Spa at Beacon
3.5 star property
Beacon
9.2 out of 10, Wonderful, (171)
"Great room, great location and super friendly staff. "
United States
Victor
The price is 7.767.645 ₫
8.942.501 ₫ total
includes taxes & fees
28 Dec - 29 Dec
The Dutchess Inn and Spa at Beacon
Bar (on property)
The Thayer Hotel at West Point

The Thayer Hotel at West Point

The Thayer Hotel at West Point
3.5 star property
West Point
9.0 out of 10, Wonderful, (671)
"Location was great & staying at a historic hotel was delightful."
United States
Bobby
The price is 4.265.946 ₫
5.510.248 ₫ total
includes taxes & fees
25 Dec - 26 Dec
The Thayer Hotel at West Point
Property entrance
Mountain Creek

Mountain Creek

Mountain Creek
3.0 star property
Vernon
8.2 out of 10, Very good, (653)
"Glad i stay very nice hotel"
United States
David
The price is 7.680.698 ₫
9.264.699 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Mountain Creek
Property grounds
The Castle at Skylands Manor

The Castle at Skylands Manor

The Castle at Skylands Manor
3.5 star property
Ringwood
7.4 out of 10, Good, (391)
"If you want a quiet, historical experience, then this is the venue. It's not new, shiny - but that is not why you go there. It is a beautiful Tudor-style hotel, with old fixtures, antique windows, and the charm of a storybook castle. The innkeeper is lovely and the grounds are beautiful. We missed peak colors by a week or two and are considering a quick trip back! Buffet breakfast was just right."
United States
Lesli
The price is 5.003.270 ₫
5.849.613 ₫ total
includes taxes & fees
31 Dec - 1 Jan 2026
The Castle at Skylands Manor
Exterior
The Abbey Inn & Spa

The Abbey Inn & Spa

The Abbey Inn & Spa
4.0 star property
Peekskill
9.2 out of 10, Wonderful, (231)
"We had a very short stay but what i can say is that rooms were extremely clean, the staff was beyond courteous extremely helpful restaurants was not only beautiful but food services once again amazing.. We look foward to coming back for a longer stay and try the spa out as well.."
United States
Paul
The price is 7.439.824 ₫
9.714.032 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
The Abbey Inn & Spa
Exterior
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport
3.0 star property
Newburgh
8.2 out of 10, Very good, (698)
"Property clean rooms clean front desk the Best "
United States
Dirwin
The price is 2.554.107 ₫
3.017.038 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
Courtyard by Marriott Newburgh Stewart Airport
Free daily full breakfast
Holiday Inn Express West Point by IHG

Holiday Inn Express West Point by IHG

Holiday Inn Express West Point by IHG
2.5 star property
Fort Montgomery
9.2 out of 10, Wonderful, (216)
"Wonderful stay…excellent staff!"
United States
John
The price is 2.949.072 ₫
3.336.137 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Inn Express West Point by IHG
Exterior detail
Borland House Inn

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (144)
"Had a great stay at the the Borland House Inn a historical setting in a cute town with wonderful staff and a delicious breakfast"
United States
Deborah
Borland House Inn
Sophia Suite | Premium bedding, individually decorated, individually furnished
The Factory

The Factory

The Factory
2.0 star property
Beacon
9.8 out of 10, Exceptional, (72)
"Gorgeous little Hotel. Would 100% stay there again."
United States
Edward
The price is 7.899.300 ₫
9.094.068 ₫ total
includes taxes & fees
28 Dec - 29 Dec
The Factory
Lobby
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1011)
"Clean room, friendly staff, good breakfast"
United States
Zuriber
The price is 2.569.379 ₫
2.990.114 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Hotel Nanuet
View from property
Fairfield Inn & Suites by Marriott Goshen Middletown

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, (1001)
"Rooms were clean and as expected. Bed was a bit soft for our taste, but acceptable. Breakfast options were routine, scrambled eggs, bacon or sausage on alternating days, oatmeal, waffles, bagel, toast, English muffins... Pleasant and helpful staff, smooth check-in and check-out. Overall a pleasant place."
United States
Joon
The price is 2.659.431 ₫
3.274.424 ₫ total
includes taxes & fees
14 Jan - 15 Jan 2026
Fairfield Inn & Suites by Marriott Goshen Middletown
Apartment, 2 Double Beds (Ground Floor) | Living area | Flat-screen TV
Countryside Motel

Countryside Motel

Countryside Motel
2.0 star property
Cold Spring
7.2 out of 10, Good, (264)
"the location and the price was reasonable for a place we needed for a quick stop - 11 pm arrival 6:30 am departure"
United States
Donald
The price is 2.501.445 ₫
2.711.040 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Countryside Motel
Restaurant
Stagecoach Inn

Stagecoach Inn

Stagecoach Inn
3.5 star property
Goshen
9.6 out of 10, Exceptional, (78)
"Unique and quaint inn with lots to offer or do nothing at all except relax!"
United States
Lorna
The price is 6.187.785 ₫
7.618.612 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Stagecoach Inn
Restaurant
The Orange Inn Boutique Hotel

The Orange Inn Boutique Hotel

The Orange Inn Boutique Hotel
2.0 star property
Goshen
9.8 out of 10, Exceptional, (153)
"Great room and layout. It was perfect for my stay with my friend! "
United States
Wendy
The price is 5.266.600 ₫
6.484.503 ₫ total
includes taxes & fees
29 Dec - 30 Dec
The Orange Inn Boutique Hotel
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.
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Goosepond Mountain State Park

4.0/5 (3 reviews)
This 1,558-acre undeveloped park offers a tranquil escape with diverse trails through woods, fields, and wetlands. Bring binoculars to spot songbirds from the boardwalk that crosses marshy areas.
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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

More cheap stays in Chester

Super 8 by Wyndham Mahwah

Super 8 by Wyndham Mahwah

160 State Route 17 South Mahwah NJ
The price is 1.969.708 ₫ per night from 4 Jan to 5 Jan
1.969.708 ₫
2.257.791 ₫ total
4 Jan - 5 Jan 2026
includes taxes & fees
7.2/10 Good! (1,005 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.