Find hotels in Chester, NY from 1.736.790 ₫

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22 Dec - 23 Dec
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23 Dec - 24 Dec
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26 Dec - 28 Dec
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Our top choices for Chester hotels

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
8.6 out of 10, Excellent, (1009)
"The breakfast was a hit, the place is clean and I would stay here again."
United States
elizabeth
The price is 2.499.925 ₫
2.953.036 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Express Hotel & Suites Chester by IHG
Exterior
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 5.657.725 ₫
6.400.334 ₫ total
includes taxes & fees
29 Dec - 30 Dec
The Dominion House Bed & Breakfast
Lobby
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1007)
"Room was clean and staff was great!"
United States
Annemarie
The price is 1.978.888 ₫
2.337.562 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Hampton Inn by Hilton Middletown
Free daily English breakfast
Tru by Hilton Middletown

Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (959)
"Staff both during check in and out were great . Great stay ."
United States
david
The price is 2.478.084 ₫
2.927.236 ₫ total
includes taxes & fees
16 Jan - 17 Jan 2026
Tru by Hilton Middletown
Seasonal outdoor pool, pool umbrellas, pool loungers
LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.8 out of 10, Excellent, (33)
"We are having a great time at the hotel!!!"
United States
Ziwei
The price is 5.008.797 ₫
9.114.259 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
LEGOLAND Hotel NEW York
Room, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board
Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1006)
"The room was very clean, comfortable bed, good service and at a reasonable price."
Canada
DIMITRIOS
The price is 2.326.246 ₫
2.631.566 ₫ total
includes taxes & fees
14 Jan - 15 Jan 2026
Sleep Inn & Suites Monroe - Woodbury
Lobby
Quality Inn near Mountain Creek

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (977)
"Nice hotel. Close to golf,"
United States
Joseph
The price is 2.244.143 ₫
2.572.349 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Quality Inn near Mountain Creek
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
Terrace/patio
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

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, (1002)
"Very nice stay."
United States
Peter
The price is 2.499.925 ₫
2.828.040 ₫ total
includes taxes & fees
9 Jan - 10 Jan 2026
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
Comfort Room, 2 Double Beds | Iron/ironing board, free WiFi
High Point Motel

High Point Motel

High Point Motel
2.0 star property
Sussex
9.0 out of 10, Wonderful, (105)
"Great place to stay"
United States
Bob
The price is 2.315.720 ₫
2.584.922 ₫ total
includes taxes & fees
23 Dec - 24 Dec
High Point Motel
Comfort Room, 2 Double Beds, Non Smoking, Refrigerator & Microwave | Free WiFi, bed sheets
Sussex Motel

Sussex Motel

Sussex Motel
2.5 star property
Sussex
8.8 out of 10, Excellent, (367)
"Would come again"
United States
Vinod
The price is 2.105.200 ₫
2.349.930 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Sussex Motel
Indoor pool, open 8:30 AM to 9:30 PM, pool loungers
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, (1008)
"Clean room, friendly staff, good breakfast"
United States
Zuriber
The price is 2.567.818 ₫
2.988.299 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Hotel Nanuet
Lobby
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1016)
"Great stay and room was very nice"
United States
Emmanuel
The price is 2.567.818 ₫
3.161.626 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Hampton Inn Harriman Woodbury
Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1004)
"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 3.131.485 ₫
3.542.525 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Overlook Lodge at Bear Mountain
Reception
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, (1003)
"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 2.657.815 ₫
3.272.436 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Fairfield Inn & Suites by Marriott Goshen Middletown
Indoor pool
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very good, (1005)
"Love it, everytime we come this is the place to stay"
United States
William
The price is 2.657.552 ₫
3.006.355 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Desk, iron/ironing board, free cots/infant beds, rollaway beds
Quality Inn & Suites Fishkill South near I-84

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, (1005)
"Always stay here on my way through NY."
United States
Kathleen
The price is 2.348.614 ₫
2.656.870 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Quality Inn & Suites Fishkill South near I-84
Lobby
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.2 out of 10, Wonderful, (1000)
"Yes stay was pleasant "
United States
henry
The price is 2.460.453 ₫
2.783.387 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Comfort Suites Fishkill near Interstate 84
Exterior
Holiday Inn Express & Suites Montgomery by IHG

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, (801)
"Clean quiet and nice reception "
United States
Nick
The price is 2.368.350 ₫
2.679.196 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Montgomery by IHG
Reception
Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill
3.0 star property
Fishkill
8.6 out of 10, Excellent, (1002)
"Brayden was great"
United States
Will
The price is 2.411.243 ₫
2.727.718 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Hilton Garden Inn Fishkill
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

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.
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

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 1.968.362 ₫ per night from 4 Jan to 5 Jan
1.968.362 ₫
2.256.248 ₫ 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.