Hotels in Chester

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Mar 3 - Mar 4
Tomorrow
Mar 4 - Mar 5
This weekend
Mar 6 - Mar 8
Next weekend
Mar 13 - Mar 15

Where to stay in Chester?

Front of property
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, (1,004 reviews)
  • cleanliness
    Within a 15-minute drive of LEGOLAND® New York with an inviting indoor pool.
The price is $86
$102 total
includes taxes & fees
Mar 8 - Mar 9
Holiday Inn Express Hotel & Suites Chester by IHG
Exterior
The Dominion House Bed & Breakfast
The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233 reviews)
  • cleanliness
    Scenic New York escape minutes from LEGOLAND and premium outlets.
The price is $215
$243 total
includes taxes & fees
Mar 9 - Mar 10
The Dominion House Bed & Breakfast
Seasonal outdoor pool, pool umbrellas, sun loungers
LEGOLAND Hotel NEW York
LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.8 out of 10, Excellent, (38 reviews)
  • cleanliness
    Colorful themed hotel with magical access to LEGOLAND New York's brick-filled adventures.
The price is $270
$441 total
includes taxes & fees
Mar 26 - Mar 27
LEGOLAND Hotel NEW York
Reception
Fairfield Inn & Suites by Marriott Goshen Middletown
Fairfield Inn & Suites by Marriott Goshen Middletown
3.0 star property
Goshen
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Relaxing stay near LEGOLAND® New York with seasonal pool and complimentary perks.
The price is $93
$114 total
includes taxes & fees
Mar 12 - Mar 13
Fairfield Inn & Suites by Marriott Goshen Middletown
Exterior
Sleep Inn & Suites Monroe - Woodbury
Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,037 reviews)
  • cleanliness
    Cozy hotel near Woodbury Common Premium Outlets with free breakfast and WiFi.
The price is $101
$114 total
includes taxes & fees
Mar 26 - Mar 27
Sleep Inn & Suites Monroe - Woodbury
Restaurant
The Orange Inn Boutique Hotel
The Orange Inn Boutique Hotel
2.0 star property
Goshen
9.8 out of 10, Exceptional, (157 reviews)
  • cleanliness
    A short drive from LEGOLAND® New York, this inn delivers comfort in historic Goshen.
The price is $250
$308 total
includes taxes & fees
Mar 4 - Mar 5
The Orange Inn Boutique Hotel
Restaurant
Stagecoach Inn
Stagecoach Inn
3.5 star property
Goshen
9.6 out of 10, Exceptional, (79 reviews)
  • cleanliness
    Explore charming Goshen with easy access to LEGOLAND® just 5 minutes away.
The price is $282
$347 total
includes taxes & fees
Mar 4 - Mar 5
Stagecoach Inn
Property amenity
Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.6 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Warm indoor pool and 24-hour fitness center just minutes from LEGOLAND® New York.
The price is $93
$109 total
includes taxes & fees
Mar 7 - Mar 8
Courtyard by Marriott Middletown Goshen
Lobby
Hampton Inn by Hilton Middletown
Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Stay by the LEGOLAND® New York theme park and enjoy a refreshing outdoor pool.
The price is $94
$111 total
includes taxes & fees
Mar 19 - Mar 20
Hampton Inn by Hilton Middletown
Exterior
Microtel Inn & Suites by Wyndham Middletown
Microtel Inn & Suites by Wyndham Middletown
2.0 star property
Middletown
7.0 out of 10, Good, (999 reviews)
  • cleanliness
    Convenient lodging near LEGOLAND® New York with free breakfast to fuel family fun.
The price is $110
$130 total
includes taxes & fees
Mar 5 - Mar 6
Microtel Inn & Suites by Wyndham Middletown
Exterior
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, (704 reviews)
  • cleanliness
    Experience a comfortable stay near LEGOLAND® New York with an indoor pool.
The price is $118
$139 total
includes taxes & fees
Mar 8 - Mar 9
Holiday Inn Express & Suites Middletown - Goshen by IHG
Exterior
Candlewood Suites Middletown Goshen by IHG
Candlewood Suites Middletown Goshen by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (43 reviews)
  • cleanliness
    Cozy extended stay hotel near LEGOLAND® New York with kitchenettes and comfort.
The price is $107
$126 total
includes taxes & fees
Mar 8 - Mar 9
Candlewood Suites Middletown Goshen by IHG
Business center
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, (1,003 reviews)
  • cleanliness
    Modern and affordable lodging near outlet mall, with free WiFi and parking.
The price is $86
$106 total
includes taxes & fees
Mar 4 - Mar 5
Americas Best Value Inn at Central Valley-Woodbury
Free daily English breakfast
Tru by Hilton Middletown
Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (982 reviews)
  • cleanliness
    Convenient stay near LEGOLAND® with free amenities for families and business trips.
The price is $103
$122 total
includes taxes & fees
Mar 15 - Mar 16
Tru by Hilton Middletown
Lobby
Comfort Suites Central Valley - Woodbury
Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
7.6 out of 10, Good, (12 reviews)
The price is $98
$121 total
includes taxes & fees
Mar 9 - Mar 10
Comfort Suites Central Valley - Woodbury
Seasonal outdoor pool
Days Inn by Wyndham Middletown
Days Inn by Wyndham Middletown
2.0 star property
New Hampton
6.4 out of 10, (681 reviews)
  • cleanliness
    Convenient drive to LEGOLAND® New York with free breakfast and seasonal pool.
The price is $92
$108 total
includes taxes & fees
Mar 15 - Mar 16
Days Inn by Wyndham Middletown
Reception
The Hamlet Inn at Warwick
The Hamlet Inn at Warwick
2.5 star property
Warwick
7.6 out of 10, Good, (154 reviews)
  • cleanliness
    Modern accommodation in Warwick with free WiFi, parking, and 24-hour service.
The price is $85
$96 total
includes taxes & fees
Mar 4 - Mar 5
The Hamlet Inn at Warwick
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, (983 reviews)
  • cleanliness
    Unwind in this tranquil hotel near Legoland, with pool and fitness amenities.
The price is $122
$145 total
includes taxes & fees
Mar 8 - Mar 9
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, (1,066 reviews)
  • cleanliness
    Just minutes from Woodbury Common Premium Outlets with pool and free breakfast.
The price is $106
$130 total
includes taxes & fees
Mar 12 - Mar 13
Hampton Inn Harriman Woodbury
Free continental breakfast on weekdays
Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,006 reviews)
  • cleanliness
    Comfortable rooms 15 minutes from LEGOLAND® New York with a relaxing indoor pool.
The price is $108
$127 total
includes taxes & fees
Mar 15 - Mar 16
Sleep Inn & Suites 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.
View all properties

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
View properties in March
Currently viewing crowd sizes and weather for March.
Typical weather for Chester
March
High 8°C / low -1°C. Partly sunny.
View properties in March
8°
weather_partly_sunny
March, no crowd data, average high temperature 8 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
-1°
14°
weather_sun
April, no crowd data, average high temperature 14 degrees Celsius, average low temperature 5 degrees Celsius. Sunny most days.
5°
21°
weather_sun
May, no crowd data, average high temperature 21 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
10°
25°
weather_sun
June, no crowd data, average high temperature 25 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
29°
weather_sun
July, no crowd data, average high temperature 29 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
28°
weather_sun
August, no crowd data, average high temperature 28 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
24°
weather_sun
September, no crowd data, average high temperature 24 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
17°
weather_sun
October, no crowd data, average high temperature 17 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
8°
10°
weather_partly_sunny
November, no crowd data, average high temperature 10 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
2°
5°
ac_unit
December, no crowd data, average high temperature 5 degrees Celsius, average low temperature -2 degrees Celsius. Snow likely.
-2°
1°
ac_unit
January, no crowd data, average high temperature 1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
3°
ac_unit
February, no crowd data, average high temperature 3 degrees Celsius, average low temperature -5 degrees Celsius. Snow likely.
-5°
Monthly weather averages (˚C)

Top landmarks in Chester

The Rock Sports Complex

4.0/5 (10 reviews)
The Rock Sports Complex is 1.2 mi (2 km) from central Chester, why not stop by during your stay. If you like The Rock Sports Complex, you'll love Arrow Park Lake and Lodge and Orange County Arboretum, both just a short drive away.
See properties

Museum Village

4.5/5 (4 reviews)
Museum Village is 0.9 mi (1.5 km) from central Chester, why not stop by during your stay. If you want to experience more of the culture Chester has to offer, head to The Rock Sports Complex, Castle Fun Center, and LEGOLAND® New York.
See properties

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.

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

Check out reviews of Chester hotels guests love

Courtyard by Marriott Fishkill

Courtyard by Marriott Fishkill

10/10 Excellent
"The room was clean and the staff was very helpful . "
Keron 1-night trip
Posted 7 hours ago
Courtyard by Marriott Fishkill

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.