Find hotels in Chester, NY from 2.177.110 ₫

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Go beyond your typical stay in Chester

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9 Nov - 10 Nov
Tomorrow
10 Nov - 11 Nov
This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

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Our top choices for Chester hotels

A Simon Premium Outlet sign at Woodbury Commons.

1. Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.8 out of 10, Excellent, (1,003 reviews)
"Good place to stay."
United States
Stephanie
The price is 2.483.006 ₫
3.057.203 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express Hotel & Suites Chester by IHG
A large, two-story white house with a wrap-around porch and a small front garden.

2. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.6 out of 10, Exceptional, (241 reviews)
"Amazing! The historic home sits on 40 acres of beautiful land inviting all guests to sit back and unwind. The beautiful home is decorated exquisitely and the hosts are warm and welcoming. If you are visiting West Point this place is a short drive away. It is nestled in a beautiful area making it an excellent option for a weekend get away-whether you are going to watch an Army football game or just want to get away, you will not be disappointed."
United States
Sally
The price is 2.751.785 ₫
3.112.973 ₫ total
includes taxes & fees
11 Nov - 12 Nov
The Dominion House Bed & Breakfast
A hotel entrance with stone pillars, a covered walkway, and a bench.

3. Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,127 reviews)
"Great stay, thanks"
United States
Gina
The price is 2.879.775 ₫
3.257.744 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Sleep Inn & Suites Monroe - Woodbury
A swimming pool with colorful umbrellas and lounge chairs.

4. LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.2 out of 10, Very good, (139 reviews)
"Love this place and so does my kids. The food is not good so make sure you eat off the resort and out of the park"
United States
danielle
The price is 3.259.649 ₫
7.202.855 ₫ total
includes taxes & fees
13 Nov - 14 Nov
LEGOLAND Hotel NEW York
A modern living room with a stone accent wall, a flat-screen TV, and a fireplace. There are multiple seating options including a sofa, chairs, and a table.

5. Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
3.0 star property
Goshen
9.0 out of 10, Wonderful, (1,005 reviews)
"Clean rooms, nice staff, and convenience to Lego Land"
United States
Aeron
The price is 3.302.142 ₫
4.065.762 ₫ total
includes taxes & fees
10 Nov - 11 Nov
Fairfield Inn & Suites by Marriott Goshen Middletown
A lobby with a fireplace, seating area, and a reception desk.

6. Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,156 reviews)
"Close to restaurants and shopping, grocery store close as well."
United States
Timothy
The price is 3.024.404 ₫
3.723.798 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Hampton Inn Harriman Woodbury
A modern reception area with a curved wooden counter, seating area with colorful cushions, and pendant lighting.

7. Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,006 reviews)
"Great stay, great play area for the family in the lobby"
United States
Jarrod
The price is 2.177.110 ₫
2.571.710 ₫ total
includes taxes & fees
29 Nov - 30 Nov
Tru by Hilton Middletown
A hotel entrance with a covered walkway, a prominent sun logo, and a modern facade.

8. 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, (1,006 reviews)
"Nice, laid back hotel with great staff."
United States
William
The price is 2.893.854 ₫
3.418.363 ₫ total
includes taxes & fees
6 Dec - 7 Dec
La Quinta Inn & Suites by Wyndham Middletown-Goshen
A hotel with a modern facade, multiple floors, and a covered entrance area.

9. Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG
2.5 star property
Middletown
8.8 out of 10, Excellent, (794 reviews)
"My favorite to be staying in there"
United States
Md
The price is 2.457.408 ₫
2.902.813 ₫ total
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express & Suites Middletown - Goshen by IHG
A landscaped outdoor area with a fire feature, seating, and a pathway.

10. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very good, (1,010 reviews)
"We love taking our daughter here to swim, pool is nice & the rooms are always clean!"
United States
Jailene
The price is 2.698.029 ₫
3.187.047 ₫ total
includes taxes & fees
19 Nov - 20 Nov
Courtyard by Marriott Middletown Goshen
An outdoor patio area with seating, a fire feature, and a view of the surrounding buildings.

11. Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
3.0 star property
Middletown
9.0 out of 10, Wonderful, (798 reviews)
"My stay with my family here was fantastic."
United States
Carl
The price is 3.894.736 ₫
4.690.250 ₫ total
includes taxes & fees
16 Nov - 17 Nov
Home2 Suites by Hilton Middletown
A multi-story hotel with balconies, outdoor seating, and a well-lit facade.

12. The Orange Inn Boutique Hotel

The Orange Inn Boutique Hotel
2.0 star property
Goshen
9.8 out of 10, Exceptional, (184 reviews)
"Lovely hotel. Wonderful location, excellent restaurant"
United States
Judy
The price is 6.053.927 ₫
7.453.897 ₫ total
includes taxes & fees
16 Nov - 17 Nov
The Orange Inn Boutique Hotel
A modern dining area with a large fish tank, sofas, and wooden tables and chairs.

13. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,255 reviews)
"Great stay"
Canada
Justine
The price is 2.714.412 ₫
3.206.399 ₫ total
includes taxes & fees
6 Dec - 7 Dec
Sleep Inn & Suites Middletown - Goshen
A large, two-story house with a wrap-around porch and multiple chimneys.

14. Parkway House Goshen Family-Friendly Bed & Breakfast

Parkway House Goshen Family-Friendly Bed & Breakfast
3.0 star property
Goshen
9.8 out of 10, Exceptional, (49 reviews)
"One of the best places we’ve stayed at, highly recommended!"
United States
Aakif
The price is 3.174.152 ₫
3.908.175 ₫ total
includes taxes & fees
11 Nov - 12 Nov
Parkway House Goshen Family-Friendly Bed & Breakfast
A hotel lobby with two sofas, a coffee machine, and a view of the parking lot.

15. Americas Best Value Inn at Central Valley-Woodbury

Americas Best Value Inn at Central Valley-Woodbury
2.0 star property
Central Valley
7.2 out of 10, Good, (1,005 reviews)
"Great place, clean quiet, helpful staff"
United States
Marlon
The price is 2.534.202 ₫
3.120.140 ₫ total
includes taxes & fees
10 Nov - 11 Nov
Americas Best Value Inn at Central Valley-Woodbury
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.

16. Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.4 out of 10, Very good, (1,003 reviews)
"Room was clean, bed was comfortable."
United States
Amanda
The price is 2.241.105 ₫
2.647.305 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Hampton Inn by Hilton Middletown
Lobby

17. Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very good, (214 reviews)
"Our stay was great !"
United States
Vu andyvu
The price is 2.854.945 ₫
3.515.373 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Comfort Suites Central Valley - Woodbury
A multi-story hotel with a central courtyard, large windows, and a parking lot.

18. Microtel Inn & Suites by Wyndham Middletown

Microtel Inn & Suites by Wyndham Middletown
2.0 star property
Middletown
6.8 out of 10, (1,004 reviews)
"Very loud and quite run down"
United States
Christine
The price is 2.371.655 ₫
2.801.518 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Microtel Inn & Suites by Wyndham Middletown
A Holiday Inn Express & Suites building with a covered entrance, stone facade, and a parking area with a bench.

19. 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, (941 reviews)
"Good stay"
United States
Mike
The price is 2.918.172 ₫
3.447.283 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express & Suites Montgomery by IHG
A multi-story hotel with a modern design, featuring a parking lot in front.

20. Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (352 reviews)
"Great quick stay!"
United States
Lady
The price is 4.582.042 ₫
5.412.538 ₫ total
includes taxes & fees
29 Nov - 30 Nov
Residence Inn by Marriott Middletown Goshen
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

8.0/10 (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.
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
A bridge with a plaque reading "City of Chester Queens Park Bridge 1923".

Top Chester Hotel Reviews

A Simon Premium Outlet sign at Woodbury Commons.
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
Chester

8/10 Good

Massive big room, 2 large comfy beds. Plenty of space. Bathroom was stocked with dove products and nice big white fluffy towels. Handy for a visit to Woodbury common for shopping but extremely noisy if your room is at the back. Request a front room as this will reduce the noise of traffic. Great amenities all round, shops and stores, just down the road was Christopher’s restaurant where the food is great and we had bagels in morning in bagel girls cafe. There was a funny strong smell of...
United Kingdom
Lisa
Reviewed October 16, 2026
Holiday Inn Express Hotel & Suites Chester by IHG

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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