Hotels in Chester

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Jun 19 - Jun 21
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Jun 26 - Jun 28

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, (1,006 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 $129
$159 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 16 - Jun 17
The Dominion House Bed & Breakfast
Lobby

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very Good, (55 reviews)
The price is $98
$120 total
includes taxes & fees
Jun 21 - Jun 22
Comfort Suites Central Valley - Woodbury
Classic Quadruple Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave | Free WiFi, bed sheets

Rolling Hills Motel

Rolling Hills Motel
2.0 star property
Sussex
8.6 out of 10, Excellent, (214 reviews)
The price is $85
$95 total
includes taxes & fees
Jun 24 - Jun 25
Rolling Hills Motel
Comfort Room, 2 Double Beds | Iron/ironing board, free WiFi

High Point Motel

High Point Motel
2.0 star property
Sussex
9.2 out of 10, Wonderful, (150 reviews)
Set in Sussex, this motel offers free WiFi and parking near High Point State Park and Dryden Kuser Natural Area. After exploring the outdoors, unwind in the garden area. Newark Liberty International Airport is 89 minutes away.
The price is $92
$103 total
includes taxes & fees
Jun 15 - Jun 16
High Point Motel
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (169 reviews)
Escape to this charming Victorian B&B in Montgomery, featuring a restaurant, snack bar, and serene garden terrace. Enjoy facials and complimentary breakfast before exploring nearby City Winery Hudson Valley and Orange County Farmers Museum.
The price is $132
$154 total
includes taxes & fees
Jun 18 - Jun 19
Borland House Inn
Reception

The Hamlet Inn at Warwick

The Hamlet Inn at Warwick
2.5 star property
Warwick
7.6 out of 10, Good, (167 reviews)
Discover comfort at this Warwick hotel offering convenient amenities including complimentary WiFi and parking. The 24-hour front desk ensures round-the-clock assistance, while nearby attractions like Albert Wisner Memorial Library and Veteran's Memorial Park await exploration.
The price is $86
$97 total
includes taxes & fees
Jun 15 - Jun 16
The Hamlet Inn at Warwick
Restaurant

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1,025 reviews)
This historic hotel offers deep-tissue massages at the spa and refreshments at the bar. Just 15 minutes from Bear Mountain State Park with nearby shopping outlets, rooms include microwaves and fridges for added convenience.
The price is $169
$208 total
includes taxes & fees
Jun 15 - Jun 16
Overlook Lodge at Bear Mountain
Suite, 1 King Bed, Non Smoking | Desk, iron/ironing board, free cribs/infant beds, rollaway beds

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84
2.5 star property
Fishkill
9.0 out of 10, Wonderful, (1,016 reviews)
Located near a train station in Fishkill, this hotel offers a fitness center and free continental breakfast daily. Enjoy convenient perks like complimentary WiFi and parking. Nearby attractions include Fishkill Golf Course and Fishkill Ridge.
The price is $87
$101 total
includes taxes & fees
Jul 9 - Jul 10
Quality Inn & Suites Fishkill South near I-84
Exterior

Tin Brook Bed & Breakfast

Tin Brook Bed & Breakfast
3.0 star property
Walden
9.4 out of 10, Exceptional, (122 reviews)
Warm, inviting atmosphere awaits at this Walden B&B where complimentary breakfast energizes your day. Explore nearby attractions with ease, knowing your car is safely parked in the free lot when you return to this cozy Hudson Valley haven.
The price is $138
$156 total
includes taxes & fees
Jun 15 - Jun 16
Tin Brook Bed & Breakfast
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, (1,098 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 $118
$134 total
includes taxes & fees
Jun 21 - Jun 22
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 15 - Jun 16
Fairfield Inn & Suites by Marriott Goshen Middletown
Indoor pool

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very Good, (1,015 reviews)
This business-friendly hotel offers a complimentary airport shuttle and is only 1.6 mi from Stewart Airport. Enjoy the indoor pool after a workout in the fitness center. With free WiFi and parking, plus proximity to Resorts World, convenience meets comfort.
The price is $109
$129 total
includes taxes & fees
Jun 15 - Jun 16
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Exterior

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, (867 reviews)
Near the train station, this Montgomery hotel offers convenience with a 24-hour health club and café. Free breakfast, WiFi and parking make stays stress-free. Close to City Winery Hudson Valley and only 16 minutes from Stewart Airport.
The price is $105
$119 total
includes taxes & fees
Jun 21 - Jun 22
Holiday Inn Express & Suites Montgomery by IHG
Double Room | Bathroom | Shower, free toiletries, hair dryer, towels

Appalachian Motel

Appalachian Motel
2.0 star property
Vernon
7.6 out of 10, Good, (536 reviews)
This cozy motel offers a tranquil base for outdoor adventures near Mountain Creek Waterpark and Ski Resort. Enjoy complimentary WiFi and parking, plus convenient room service after a day exploring the hiking trails or snowboarding slopes.
The price is $68
$77 total
includes taxes & fees
Jun 28 - Jun 29
Appalachian Motel
Lobby

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,015 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 $112
$132 total
includes taxes & fees
Jun 17 - Jun 18
Hampton Inn by Hilton Middletown
Suite, 1 King Bed, Non Smoking (1 Bedroom) | In-room safe, desk, iron/ironing board, free cribs/infant beds

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (624 reviews)
The price is $118
$133 total
includes taxes & fees
Jun 15 - Jun 16
Days Inn by Wyndham Wurtsboro
Free daily continental breakfast

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
8.2 out of 10, Very Good, (127 reviews)
The price is $93
$107 total
includes taxes & fees
Jul 2 - Jul 3
Spark by Hilton Fishkill
Lobby

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (1,002 reviews)
Wake up to mountain tranquility at this Vernon retreat, just a 10-minute drive from Crystal Springs Golf Resort and Mountain Creek Ski Resort. After days of downhill adventures or hiking, return to clean rooms and helpful staff. Free breakfast, WiFi, and parking add value.
The price is $99
$114 total
includes taxes & fees
Jul 2 - Jul 3
Quality Inn near Mountain Creek
Reception

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport
2.5 star property
Newburgh
9.2 out of 10, Wonderful, (1,003 reviews)
The price is $122
$144 total
includes taxes & fees
Jun 21 - Jun 22
Hampton Inn & Suites Newburgh Stewart Airport
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
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.
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21°
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May, no crowd data, average high temperature 21 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
10°
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 Orange County Arboretum and Arrow Park Lake and Lodge, 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

Studio 6 Extended Stay Fishkill Westage Center NY

Studio 6 Extended Stay Fishkill Westage Center NY

2/10 Terrible
"Just awful on every level. Rooms, stairwells, property filthy and run down. Check in person rude and dismissive. People smoking cigarettes outside entrance doors. Had I not been staying only one night I would have not even made it through. A horrible experience."
francine 1-night trip
Posted less than an hour ago
Studio 6 Extended Stay Fishkill Westage Center NY

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.