Hotels in Chester
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Where to stay in Chester?
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, (1005)
8.6/10
Excellent
(1005)
- Within a 15-minute drive of LEGOLAND® New York with an inviting indoor pool.
The price is $84
$84
$99 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Dominion House Bed & Breakfast
The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233)
9.2/10
Wonderful
(233)
- Scenic New York escape minutes from LEGOLAND and premium outlets.
The price is $215
$215
$243 total
includes taxes & fees
Dec 30 - Dec 31
LEGOLAND Hotel NEW York
LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.8 out of 10, Excellent, (33)
8.8/10
Excellent
(33)
- Colorful themed hotel with magical access to LEGOLAND New York's brick-filled adventures.
The price is $190
$190
$346 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Sleep Inn & Suites Monroe - Woodbury
Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1007)
9.4/10
Exceptional
(1007)
- Cozy hotel near Woodbury Common Premium Outlets with free breakfast and WiFi.
The price is $85
$85
$96 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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)
8.8/10
Excellent
(1001)
- Relaxing stay near LEGOLAND® New York with seasonal pool and complimentary perks.
The price is $101
$101
$124 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Orange Inn Boutique Hotel
The Orange Inn Boutique Hotel
2.0 star property
Goshen
9.8 out of 10, Exceptional, (153)
9.8/10
Exceptional
(153)
- A short drive from LEGOLAND® New York, this inn delivers comfort in historic Goshen.
The price is $250
$250
$308 total
includes taxes & fees
Dec 29 - Dec 30
Stagecoach Inn
Stagecoach Inn
3.5 star property
Goshen
9.6 out of 10, Exceptional, (78)
9.6/10
Exceptional
(78)
- Explore charming Goshen with easy access to LEGOLAND® just 5 minutes away.
The price is $235
$235
$289 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn by Hilton Middletown
Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1005)
8.6/10
Excellent
(1005)
- Stay by the LEGOLAND® New York theme park and enjoy a refreshing outdoor pool.
The price is $72
$72
$85 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.6 out of 10, Excellent, (1000)
8.6/10
Excellent
(1000)
- Warm indoor pool and 24-hour fitness center just minutes from LEGOLAND® New York.
The price is $97
$97
$114 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Tru by Hilton Middletown
Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (959)
8.6/10
Excellent
(959)
- Convenient stay near LEGOLAND® with free amenities for families and business trips.
The price is $94
$94
$111 total
includes taxes & fees
Jan 16 - Jan 17, 2026
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, (1000)
7.2/10
Good
(1000)
- Modern and affordable lodging near outlet mall, with free WiFi and parking.
The price is $86
$86
$106 total
includes taxes & fees
Jan 7 - Jan 8, 2026
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, (697)
8.8/10
Excellent
(697)
- Experience a comfortable stay near LEGOLAND® New York with an indoor pool.
The price is $118
$118
$139 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Days Inn by Wyndham Middletown
Days Inn by Wyndham Middletown
2.0 star property
New Hampton
6.4 out of 10, (677)
6.4/10
(677)
- Convenient drive to LEGOLAND® New York with free breakfast and seasonal pool.
The price is $84
$84
$99 total
includes taxes & fees
Dec 29 - Dec 30
Candlewood Suites Middletown Goshen by IHG
Candlewood Suites Middletown Goshen by IHG
2.5 star property
Middletown
9.0 out of 10, Wonderful, (34)
9.0/10
Wonderful
(34)
- Cozy extended stay hotel near LEGOLAND® New York with kitchenettes and comfort.
The price is $129
$129
$152 total
includes taxes & fees
Dec 28 - Dec 29
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, (944)
9.4/10
Exceptional
(944)
- Unwind in this tranquil hotel near Legoland, with pool and fitness amenities.
The price is $122
$122
$144 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Hamlet Inn at Warwick
The Hamlet Inn at Warwick
2.5 star property
Warwick
7.6 out of 10, Good, (152)
7.6/10
Good
(152)
- Modern accommodation in Warwick with free WiFi, parking, and 24-hour service.
The price is $95
$95
$107 total
includes taxes & fees
Dec 28 - Dec 29
Microtel Inn & Suites by Wyndham Middletown
Microtel Inn & Suites by Wyndham Middletown
2.0 star property
Middletown
7.0 out of 10, Good, (1000)
7.0/10
Good
(1000)
- Convenient lodging near LEGOLAND® New York with free breakfast to fuel family fun.
The price is $101
$101
$120 total
includes taxes & fees
Dec 29 - Dec 30
Hampton Inn Harriman Woodbury
Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1018)
9.2/10
Wonderful
(1018)
- Just minutes from Woodbury Common Premium Outlets with pool and free breakfast.
The price is $98
$98
$120 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.6 out of 10, Excellent, (1004)
8.6/10
Excellent
(1004)
- Comfortable rooms 15 minutes from LEGOLAND® New York with a relaxing indoor pool.
The price is $104
$104
$123 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Super 8 by Wyndham Middletown
Super 8 by Wyndham Middletown
2.5 star property
Middletown
6.0 out of 10, (1000)
6.0/10
(1000)
- Quiet retreat with nearby dining options and easy access to LEGOLAND New York.
The price is $78
$78
$92 total
includes taxes & fees
Jan 1 - Jan 2, 2026
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.
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.
Go beyond your typical stay in Chester
Family friendly
Apartment
Pet friendly
Cottage
When is the best time to visit Chester?
When is the best time to visit Chester?Our prices for hotels in Chester are cheapest in December
When is the best time to visit Chester?
When is the best time to visit Chester?
Our prices for hotels in Chester are cheapest in December
Price trends for hotels in Chester
Pricing is based on two traveler single night rates
Currently viewing crowd sizes and weather for December.
Typical weather for Chester
December
High crowds
High 5°C / low -2°C. Snow likely.
View properties in December 5°
December, High crowds, average high temperature 5 degrees Celsius, average low temperature -2 degrees Celsius. Snow likely.
-2°
1°
January, Low crowds, average high temperature 1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
3°
February, Low crowds, average high temperature 3 degrees Celsius, average low temperature -5 degrees Celsius. Snow likely.
-5°
8°
March, Low crowds, average high temperature 8 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
-1°
14°
April, Moderate crowds, average high temperature 14 degrees Celsius, average low temperature 5 degrees Celsius. Sunny most days.
5°
21°
May, High crowds, average high temperature 21 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
10°
25°
June, Moderate crowds, average high temperature 25 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
29°
July, High crowds, average high temperature 29 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
28°
August, High crowds, average high temperature 28 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
24°
September, Low crowds, average high temperature 24 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
17°
October, Moderate crowds, average high temperature 17 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
8°
10°
November, Moderate crowds, average high temperature 10 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
2°
Monthly weather averages (˚C)
Top landmarks in Chester
Learn more about Chester
Chester is well-known for its attractions such as Castle Fun Center and The Rock Sports Complex. Visitors to this family-friendly city speak highly of the restaurants whereas sights include Museum Village and Goosepond Mountain State Park.
Check out reviews of Chester hotels guests love
Hampton Inn & Suites Mahwah
10/10 Excellent
"Clean room "
Hampton Inn by Hilton Middletown
10/10 Excellent
"Very well service "
Hampton Inn Nanuet
10/10 Excellent
"Everything was perfect and enjoyable. "
DoubleTree by Hilton Hotel Nanuet
10/10 Excellent
"Nice people and a nice clean and spacious room. Thank you "
Hampton Inn Harriman Woodbury
10/10 Excellent
"Great breakfast options "
Sonesta Simply Suites Nanuet
10/10 Excellent
"Spacious"
Crowne Plaza Suffern - Mahwah by IHG
10/10 Excellent
"Room was very clean, modern, nice amenities, nice open lobby with plenty of areas to sit and relax, nice bar, nice gym, and hotel staff very helpful and price was reasonable. One of the best hotels I've stayed at. 5 stars. "
Overlook Lodge at Bear Mountain
10/10 Excellent
"The staff were wonderful. Everyone (maintenance, front desk, restaurant, spa) was very helpful and welcoming. I throughly enjoyed my staff and look forward to visiting again."
Howard Johnson by Wyndham Newburgh/West Point
10/10 Excellent
"Love the stay"
Frequently asked questions
What accommodations do travelers recommend in Chester?
Holiday Inn Express Hotel & Suites Chester by IHG is a property that our guests really like.
Can I book refundable hotels in Chester?
If you're looking for the flexibility to change your plans to Chester, most accommodations offer refundable* rates you can book. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.
Where should I consider staying in Chester if I'm looking for a budget-friendly accommodation?
An inexpensive option worth considering is Holiday Inn Express Hotel & Suites Chester by IHG.
Where can I stay in Chester if I want a vacation rental instead of a hotel?
Browse 10 vacation homes on our site.
What will the weather in Chester be like during my vacation?
July and August are typically the warmest months in Chester when the average temp is 70°F. January and February are the coldest months when the average temperature is 32°F. July and October are the months with the most rain.
Why should I book my Chester hotel with Hotels.com?
There are lots of reasons to book your Chester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.