Hotels in Chester

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Jul 17 - Jul 19
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Jul 24 - Jul 26

Where to stay in Chester?

Lobby

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very Good, (72 reviews)
The price is $97
$119 total
includes taxes & fees
Aug 12 - Aug 13
Comfort Suites Central Valley - Woodbury
Exterior

Tin Brook Bed & Breakfast

Tin Brook Bed & Breakfast
3.0 star property
Walden
9.4 out of 10, Exceptional, (125 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
Jul 14 - Jul 15
Tin Brook Bed & Breakfast
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
8.4 out of 10, Very Good, (219 reviews)
The price is $77
$86 total
includes taxes & fees
Jul 26 - Jul 27
Rolling Hills Motel
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, (1,025 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 $98
$121 total
includes taxes & fees
Jul 26 - Jul 27
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
Jul 15 - Jul 16
The Dominion House Bed & Breakfast
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (170 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 $121
$141 total
includes taxes & fees
Jul 15 - Jul 16
Borland House Inn
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, (162 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
Jul 14 - Jul 15
High Point Motel
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, (884 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 $91
$102 total
includes taxes & fees
Jul 26 - Jul 27
Holiday Inn Express & Suites Montgomery by IHG
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, (1,108 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 $108
$122 total
includes taxes & fees
Aug 4 - Aug 5
Sleep Inn & Suites Monroe - Woodbury
Reception

The Hamlet Inn at Warwick

The Hamlet Inn at Warwick
2.5 star property
Warwick
7.6 out of 10, Good, (173 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
Jul 14 - Jul 15
The Hamlet Inn at Warwick
Suite, 1 King Bed, Non Smoking (1 Bedroom) | In-room safe, desk, laptop workspace, iron/ironing board

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (631 reviews)
The price is $114
$129 total
includes taxes & fees
Jul 19 - Jul 20
Days Inn by Wyndham Wurtsboro
Exterior

Holiday Inn Express West Point by IHG

Holiday Inn Express West Point by IHG
2.5 star property
Fort Montgomery
9.0 out of 10, Wonderful, (264 reviews)
Retreat to comfort just a 5-minute walk from Bear Mountain State Park. This hotel features an inviting indoor pool, relaxing sauna, and steam room. Enjoy free breakfast, WiFi, and parking, plus in-room refrigerators and microwaves for added convenience.
The price is $119
$140 total
includes taxes & fees
Jul 19 - Jul 20
Holiday Inn Express West Point by IHG
Restaurant

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1,011 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
Jul 14 - Jul 15
Overlook Lodge at Bear Mountain
Lobby

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (1,004 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 $92
$106 total
includes taxes & fees
Jul 26 - Jul 27
Quality Inn near Mountain Creek
Free continental breakfast on weekdays

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,077 reviews)
Wake up to a complimentary breakfast before exploring nearby attractions like LEGOLAND® New York and Paramount Theatre. After sightseeing, enjoy a refreshing swim in the indoor pool or visit the 24-hour fitness center. Free WiFi and parking enhance your stay.
The price is $112
$132 total
includes taxes & fees
Aug 5 - Aug 6
Sleep Inn & Suites Middletown - Goshen
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, (1,012 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 $100
$116 total
includes taxes & fees
Aug 9 - Aug 10
Quality Inn & Suites Fishkill South near I-84
Interior entrance

Holiday Inn Express Haskell - Wayne Area by IHG

Holiday Inn Express Haskell - Wayne Area by IHG
2.5 star property
Wanaque
9.0 out of 10, Wonderful, (1,005 reviews)
This Wanaque hotel offers an indoor pool and 24-hour fitness center, plus free breakfast, WiFi, and parking. Clean rooms provide a comfortable base for exploring nearby Rhino Theatre and Glen Wild Lake. The helpful staff ensures a pleasant business or leisure stay.
The price is $127
$145 total
includes taxes & fees
Jul 23 - Jul 24
Holiday Inn Express Haskell - Wayne Area by IHG
Exterior

Holiday Inn Express Ramsey-Mahwah by IHG

Holiday Inn Express Ramsey-Mahwah by IHG
2.5 star property
Ramsey
9.2 out of 10, Wonderful, (1,006 reviews)
Surprisingly peaceful stay awaits at this business-friendly hotel in Ramsey. Enjoy the 24-hour fitness center, free daily buffet breakfast, and complimentary WiFi and parking. The helpful staff ensures comfort while you explore nearby Tice's Corner attractions.
The price is $114
$131 total
includes taxes & fees
Jul 23 - Jul 24
Holiday Inn Express Ramsey-Mahwah by IHG
Lobby sitting area

The Thayer Hotel at West Point

The Thayer Hotel at West Point
3.5 star property
West Point
9.0 out of 10, Wonderful, (760 reviews)
Perched along the Hudson River, this stately hotel combines military tradition with modern comfort. Explore Bear Mountain State Park and West Point Museum nearby. The attentive staff delivers exceptional service in this well-maintained riverside retreat.
The price is $203
$266 total
includes taxes & fees
Jul 15 - Jul 16
The Thayer Hotel at West Point
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 July
Currently viewing crowd sizes and weather for July.
Typical weather for Chester
July
High 29°C / low 18°C. Sunny most days.
View properties in July
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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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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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June, no crowd data, average high temperature 25 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
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Monthly weather averages (ËšC)

Top landmarks in Chester

The Rock Sports Complex

8.0/10 (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
A bridge with a plaque reading "City of Chester Queens Park Bridge 1923".

Check out reviews of Chester hotels guests love

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"The breakfast was excellent and the rooms were lovely. The pool is disappointing because it is super tiny and there was a private group swim lesson while we were there which took up half the space."
Doris 2-night trip
Posted less than an hour ago
Sleep Inn & Suites Middletown - Goshen

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 10 vacation homes on our site. Also think about one of the 7 villas for your getaway.
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 Keyâ„¢, our rewards program, you will be able to earn and use OneKeyCashâ„¢* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.