Hotels in Chester

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Jun 12 - Jun 14
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Jun 19 - Jun 21

Where to stay in Chester?

Exterior

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)
This conveniently located Chester hotel offers free perks including WiFi, parking, and weekday breakfast. Splash in the indoor pool after exploring nearby Woodbury Common Premium Outlets. Guests consistently praise the helpful staff and clean rooms.
The price is $116
$143 total
includes taxes & fees
Jun 15 - Jun 16
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, (235 reviews)
Unwind at this charming B&B with a refreshing outdoor pool, lush garden, and peaceful terrace. After complimentary breakfast, explore nearby hiking trails or head to LEGOLAND and Woodbury Common Premium Outlets, both within 15 minutes.
The price is $215
$243 total
includes taxes & fees
Jun 9 - Jun 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, (48 reviews)
Imagination comes alive at this playful retreat steps from LEGOLAND® New York. Families can enjoy the outdoor pool after park adventures, then recharge with complimentary breakfast before building more memories. The on-site restaurant and bar complete your magical brick-filled escape.
The price is $300
$476 total
includes taxes & fees
Jun 7 - Jun 8
LEGOLAND Hotel NEW York
Room, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,090 reviews)
Wake up to a complimentary breakfast at this Monroe hotel, just minutes from LEGOLAND® and premium shopping. The fitness center energizes your day while in-room refrigerators and microwaves offer convenience after exploring nearby Museum Village.
The price is $113
$127 total
includes taxes & fees
Jun 15 - Jun 16
Sleep Inn & Suites Monroe - Woodbury
Reception

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, (1,001 reviews)
Wake up to a free breakfast at this Goshen hotel, just 5 minutes from LEGOLAND® New York. Cool off in the seasonal outdoor pool or maintain your routine at the 24-hour fitness center. Guests love the helpful staff and convenient free parking and WiFi.
The price is $144
$177 total
includes taxes & fees
Jun 7 - Jun 8
Fairfield Inn & Suites by Marriott Goshen Middletown
Cottage (2 Bedrooms) | Interior

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
The price is $183
$515 total
includes taxes & fees
Jul 2 - Jul 3
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Restaurant

The Orange Inn Boutique Hotel

The Orange Inn Boutique Hotel
2.0 star property
Goshen
9.8 out of 10, Exceptional, (162 reviews)
Escape to this boutique hotel where 6 coffee shops keep you energized between LEGOLAND® New York adventures. With a restaurant, bar, and free WiFi, you'll enjoy easy access to local attractions while the helpful staff ensures a memorable stay.
The price is $275
$339 total
includes taxes & fees
Jun 8 - Jun 9
The Orange Inn Boutique Hotel
Design Apartment, Patio, Garden View | View from room

Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is $311
$382 total
includes taxes & fees
Jun 18 - Jun 19
Historic Horse Barn Apartment in Goshen
Restaurant

Stagecoach Inn

Stagecoach Inn
3.5 star property
Goshen
9.6 out of 10, Exceptional, (79 reviews)
Unwind at this cozy B&B featuring a lovely garden and terrace. Enjoy complimentary breakfast and room service after a day of adventures at LEGOLAND® New York or the nearby Harness Racing Museum and Hall of Fame.
The price is $278
$342 total
includes taxes & fees
Jun 10 - Jun 11
Stagecoach Inn
Lobby

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,007 reviews)
This quiet Middletown hotel offers a seasonal outdoor pool and free breakfast just minutes from LEGOLAND® New York. Clean rooms provide comfort after visiting the Galleria at Crystal Run mall. With free WiFi and parking, plus fitness center access, guests praise the helpful staff.
The price is $105
$124 total
includes taxes & fees
Jun 16 - Jun 17
Hampton Inn by Hilton Middletown
Property amenity

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very Good, (1,003 reviews)
Enjoy American cuisine at The Bistro or unwind at the bar after exploring nearby LEGOLAND® and Galleria at Crystal Run. This Middletown hotel offers free WiFi, free parking, and is praised for its exceptionally helpful staff.
The price is $114
$135 total
includes taxes & fees
Jun 14 - Jun 15
Courtyard by Marriott Middletown Goshen
Miscellaneous

Inn at Stony Creek

Inn at Stony Creek
3.0 star property
Warwick
9.2 out of 10, Wonderful, (458 reviews)
The price is $231
$261 total
includes taxes & fees
Jun 7 - Jun 8
Inn at Stony Creek
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)
Wake up refreshed at this welcoming Middletown hotel where complimentary continental breakfast jumpstarts your day. Just a short drive from LEGOLAND® New York and Galleria at Crystal Run, enjoy free WiFi and parking while helpful staff ensure a pleasant stay.
The price is $105
$125 total
includes taxes & fees
Jun 14 - Jun 15
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, (725 reviews)
Situated just minutes from LEGOLAND® New York and Galleria at Crystal Run, this hotel offers a refreshing indoor pool and fitness center. Enjoy complimentary breakfast, WiFi, and parking while the helpful staff ensures a pleasant stay in clean, business-friendly accommodations.
The price is $146
$172 total
includes taxes & fees
Jun 10 - Jun 11
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, (59 reviews)
Set in Middletown, this hotel offers convenient access to LEGOLAND® New York and Galleria at Crystal Run. Just 28 minutes from Stewart Intl. Airport and 22 minutes from Harriman Station, it's perfectly positioned for regional exploration.
The price is $139
$164 total
includes taxes & fees
Jun 8 - Jun 9
Candlewood Suites Middletown Goshen by IHG
House (4 Bedrooms) | Interior

Family Home Close to Warwick, 5 Mi to Lake!

Family Home Close to Warwick, 5 Mi to Lake!
3.0 star property
Monroe
The price is $281
$730 total
includes taxes & fees
Jun 10 - Jun 11
Family Home Close to Warwick, 5 Mi to Lake!
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, (1,006 reviews)
Central Valley motel just 15 minutes from Woodbury Common Premium Outlets and LEGOLAND New York. Guests praise the helpful staff, clean rooms, and overall value. Enjoy complimentary WiFi and parking, plus easy access to Bear Mountain State Park and Old Glory Mall.
The price is $99
$122 total
includes taxes & fees
Jun 7 - Jun 8
Americas Best Value Inn at 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, (687 reviews)
Wake up to a complimentary on-the-go breakfast at this motel before heading to nearby LEGOLAND® New York, just a 10-minute drive away. Take a refreshing dip in the seasonal outdoor pool after exploring Soons Orchards in the area.
The price is $101
$120 total
includes taxes & fees
Jun 8 - Jun 9
Days Inn by Wyndham Middletown
Lobby

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.2 out of 10, Very Good, (51 reviews)
The price is $100
$123 total
includes taxes & fees
Jun 15 - Jun 16
Comfort Suites Central Valley - Woodbury
Lobby

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,116 reviews)
Wake up to a complimentary breakfast at this convenient hotel near shopping destinations. The indoor pool offers year-round relaxation after exploring nearby attractions. Rooms include refrigerators and microwaves, with free WiFi and parking completing your comfortable stay.
The price is $122
$150 total
includes taxes & fees
Jun 14 - Jun 15
Hampton Inn Harriman Woodbury
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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When is the best time to visit Chester?

Our prices for hotels in Chester are cheapest in March
Price trends for hotels in Chester
Pricing is based on two traveler single night rates
View properties in June
Currently viewing crowd sizes and weather for June.
Typical weather for Chester
June
High 25°C / low 15°C. Sunny most days.
View properties in June
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June, no crowd data, average high temperature 25 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
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July, no crowd data, average high temperature 29 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
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August, no crowd data, average high temperature 28 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
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September, no crowd data, average high temperature 24 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
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October, no crowd data, average high temperature 17 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
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November, no crowd data, average high temperature 10 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
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December, no crowd data, average high temperature 5 degrees Celsius, average low temperature -2 degrees Celsius. Snow likely.
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January, no crowd data, average high temperature 1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
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February, no crowd data, average high temperature 3 degrees Celsius, average low temperature -5 degrees Celsius. Snow likely.
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March, no crowd data, average high temperature 8 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
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April, no crowd data, average high temperature 14 degrees Celsius, average low temperature 5 degrees Celsius. Sunny most days.
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May, no crowd data, average high temperature 21 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
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Monthly weather averages (˚C)

Top landmarks in Chester

The Rock Sports Complex

4.0/5 (18 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.
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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
The Queens Park Bridge, a landmark of Chester

Check out reviews of Chester hotels guests love

Spark by Hilton Fishkill

Spark by Hilton Fishkill

8/10 Good
"The location is very good, near Fishkill and the highway but on a Friday night drivers without mufflers were making a lot of noise right up to midnight. It’s something they do regularly, I’m told. Also, the heater in our room was hard to regulate and a bit noisy. The breakfast was all right."
Anne 3-night trip
Posted 1 hour ago
Spark by Hilton Fishkill

Frequently asked questions

What accommodations do travelers recommend in Chester?
Guests like Holiday Inn Express Hotel & Suites Chester by IHG, La Quinta Inn & Suites by Wyndham Middletown-Goshen and Hampton Inn Harriman Woodbury.
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 9 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.