Hotels in Chester

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This weekend
May 22 - May 24
Next weekend
May 29 - May 31

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, (1,000 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 $108
$133 total
includes taxes & fees
May 25 - May 26
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)
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
May 25 - May 26
The Dominion House Bed & Breakfast
View from property

Inn on the Hudson

Inn on the Hudson
2.0 star property
Peekskill
7.0 out of 10, Good, (1,000 reviews)
Perched along the Hudson, this inn provides free breakfast, WiFi and parking. Explore nearby Bear Mountain State Park or stroll to Peekskill Landing Park. Rooms include refrigerators and microwaves for added convenience.
The price is $109
$125 total
includes taxes & fees
May 24 - May 25
Inn on the Hudson
Exterior

The Abbey Inn & Spa

The Abbey Inn & Spa
4.0 star property
Peekskill
9.2 out of 10, Wonderful, (247 reviews)
This Peekskill hotel features Apropos Restaurant, a rejuvenating full-service spa, and a seasonal outdoor pool. Located near Bear Mountain State Park, guests can explore local attractions or work out in the fitness center. Staff earn high praise for their exceptional service.
The price is $387
$488 total
includes taxes & fees
May 26 - May 27
The Abbey Inn & Spa
Free daily self-serve breakfast

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
2.5 star property
Peekskill
9.2 out of 10, Wonderful, (1,003 reviews)
Wake up to a complimentary breakfast at this Peekskill hotel before exploring Bear Mountain State Park nearby. The indoor pool offers year-round swimming, while free WiFi and parking add convenience. Located near the train station for easy Hudson Valley excursions.
The price is $148
$169 total
includes taxes & fees
May 28 - May 29
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
Indoor pool, open 8:30 AM to 9:30 PM, sun loungers

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1,134 reviews)
Steps from Rockland Bakery and The Shops at Nanuet, this tranquil hotel offers an indoor pool and Windsor Grille for dinner. With a bar, 24-hour fitness center, and free WiFi and parking, enjoy a quiet, relaxing stay near Mahwah Station.
The price is $118
$137 total
includes taxes & fees
Jun 1 - Jun 2
DoubleTree by Hilton Hotel Nanuet
Exterior

Hampton Inn Fishkill

Hampton Inn Fishkill
2.5 star property
Fishkill
8.6 out of 10, Excellent, (1,000 reviews)
Stay at this serene hotel with an indoor pool near Van Wyck Homestead Museum and Fishkill Golf Course. Just 17 minutes from Stewart Airport, guests praise the helpful staff and peaceful atmosphere. Enjoy free breakfast, WiFi, and parking during your visit.
The price is $111
$128 total
includes taxes & fees
Jun 7 - Jun 8
Hampton Inn Fishkill
Free daily continental breakfast

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
8.0 out of 10, Very Good, (97 reviews)
The price is $93
$107 total
includes taxes & fees
Jun 2 - Jun 3
Spark by Hilton Fishkill
Exterior

Best Western Fishkill Inn & Suites

Best Western Fishkill Inn & Suites
3.5 star property
Fishkill
8.8 out of 10, Excellent, (1,000 reviews)
Experience Fishkill's peaceful atmosphere at this well-reviewed hotel with free breakfast, WiFi, and parking. Take a refreshing dip in the seasonal outdoor pool or stay fit at the gym. The clean rooms include microwaves and refrigerators for added convenience.
The price is $143
$165 total
includes taxes & fees
May 25 - May 26
Best Western Fishkill Inn & Suites
View from property

Courtyard by Marriott Fishkill

Courtyard by Marriott Fishkill
3.0 star property
Fishkill
8.8 out of 10, Excellent, (770 reviews)
Relax at this tranquil retreat just minutes from the Van Wyck Homestead Museum. Take a refreshing dip in the indoor pool, grab dinner at The Bistro, or maintain your routine at the fitness center. Free WiFi and parking enhance your convenient stay.
The price is $125
$142 total
includes taxes & fees
Jun 10 - Jun 11
Courtyard by Marriott Fishkill
Reception

Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill
3.0 star property
Fishkill
8.6 out of 10, Excellent, (1,005 reviews)
Unwind at this Hudson Valley hotel with an indoor pool, convenient dining at Great American Grille, and a 24-hour fitness center. Each room includes a refrigerator and microwave, while free parking and WiFi add value for exploring nearby museums and golf courses.
The price is $130
$151 total
includes taxes & fees
May 26 - May 27
Hilton Garden Inn Fishkill
Exterior

Studio 6 Extended Stay Fishkill Route 9 NY

Studio 6 Extended Stay Fishkill Route 9 NY
2.5 star property
Fishkill
6.6 out of 10, (1,001 reviews)
Escape to a quiet haven in Fishkill where hiking trails and mountain biking await. This hotel offers convenient free perks including Wi-Fi, parking, and daily on-the-go breakfast. Located near Van Wyck Homestead Museum, it's a tranquil base for outdoor enthusiasts.
The price is $80
$92 total
includes taxes & fees
Jun 1 - Jun 2
Studio 6 Extended Stay Fishkill Route 9 NY
BBQ/picnic area

SpringHill Suites by Marriott Fishkill

SpringHill Suites by Marriott Fishkill
3.0 star property
Fishkill
9.6 out of 10, Exceptional, (1,000 reviews)
Quiet retreat with a 24-hour fitness center and onsite dining options where you can relax with a drink at the bar. Free perks include breakfast, WiFi, and parking. Near Van Wyck Homestead Museum and praised for helpful staff.
The price is $159
$184 total
includes taxes & fees
May 31 - Jun 1
SpringHill Suites by Marriott Fishkill
Premium bedding, pillowtop beds, desk, laptop workspace

HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie
3.0 star property
Fishkill
8.8 out of 10, Excellent, (1,000 reviews)
Warm ambiance meets convenience at this Fishkill hotel near Van Wyck Homestead Museum. Enjoy the indoor pool and hot tub after exploring, then grab a drink at the bar. Clean rooms with microwaves and refrigerators add comfort to your stay.
The price is $156
$180 total
includes taxes & fees
Jun 1 - Jun 2
HYATT house Fishkill/Poughkeepsie
Terrace/patio

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, (1,009 reviews)
Wake up refreshed at this welcoming Fishkill hotel offering free breakfast, WiFi and parking. Unwind in the indoor pool and hot tub after exploring nearby Van Wyck Homestead Museum. Clean rooms with microwaves and refrigerators enhance your Hudson Valley stay.
The price is $130
$150 total
includes taxes & fees
May 25 - May 26
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
Property amenity

Residence Inn by Marriott Fishkill

Residence Inn by Marriott Fishkill
3.0 star property
Fishkill
9.4 out of 10, Exceptional, (423 reviews)
This extended-stay hotel offers an indoor pool and 24-hour fitness center near Van Wyck Homestead Museum. Enjoy free breakfast, WiFi, and parking, plus in-room refrigerators and microwaves. Staff earn praise from travelers and Stewart Airport is just 22 minutes away.
The price is $159
$184 total
includes taxes & fees
May 25 - May 26
Residence Inn by Marriott Fishkill
Apartment, 2 Double Beds (Ground Floor) | Living area | Flat-screen TV

Countryside Motel

Countryside Motel
2.0 star property
Cold Spring
7.2 out of 10, Good, (266 reviews)
Minutes from Fishkill Ridge hiking trails, this cozy Cold Spring motel offers free WiFi and parking. Enjoy daily housekeeping and easy access to nearby Fishkill Golf Course for a relaxing Hudson Valley escape.
The price is $95
$103 total
includes taxes & fees
May 20 - May 21
Countryside Motel
Free WiFi, bed sheets

Budget Motor Inn - Stony Point

Budget Motor Inn - Stony Point
1.5 star property
Stony Point
5.2 out of 10, (554 reviews)
This simple hotel in Stony Point offers free WiFi and parking, plus 24-hour front desk service. Just a 10-minute drive from Bear Mountain State Park and close to Penguin Rep Theatre, it's an affordable base for exploring nearby attractions.
The price is $62
$69 total
includes taxes & fees
May 20 - May 21
Budget Motor Inn - Stony Point
Lobby

Element by Marriott Spring Valley

Element by Marriott Spring Valley
3.0 star property
Spring Valley
8.8 out of 10, Excellent, (483 reviews)
The price is $153
$178 total
includes taxes & fees
May 25 - May 26
Element by Marriott Spring Valley
Premium bedding, pillowtop beds, in-room safe, desk

Hampton Inn Nanuet

Hampton Inn Nanuet
2.5 star property
Nanuet
7.8 out of 10, Good, (1,000 reviews)
Wake up to free breakfast at this welcoming Nanuet hotel near The Shops at Nanuet. Enjoy morning laps in the indoor pool or hit the fitness center. With free WiFi, parking, and helpful staff, this spot makes exploring Rockland County hassle-free.
The price is $106
$123 total
includes taxes & fees
May 31 - Jun 1
Hampton Inn Nanuet
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 May
Currently viewing crowd sizes and weather for May.
Typical weather for Chester
May
High 21°C / low 10°C. Sunny most days.
View properties in May
21°
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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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25°
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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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29°
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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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28°
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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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24°
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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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17°
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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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14°
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April, no crowd data, average high temperature 14 degrees Celsius, average low temperature 5 degrees Celsius. Sunny most days.
5°
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
Black dirt region farm Chester New York

Check out reviews of Chester hotels guests love

Studio 6 Extended Stay Fishkill Route 9 NY

Studio 6 Extended Stay Fishkill Route 9 NY

2/10 Terrible
"Was not able to stay there due to accommodations. It’s a good thing though. The place smelt like dog urine and looked run down. Still waiting on my refund and it’s been 5 days. "
Larry 4-night trip
Posted 1 hour ago
Studio 6 Extended Stay Fishkill Route 9 NY

Frequently asked questions

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