Book Hotels in Chester, NY

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Top Chester hotels

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd Suffern NY
Fully refundable
$110 nightly
The price is $128 total per night from Aug 9 to Aug 10
$128 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel features a restaurant and 2 bars/lounges. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy ...
"I had my dog with me and the property was very accommodating. The room was clean and the grounds were beautiful and well kept. My only suggestion would be to have a bartender and a waitress at the lounge. Our bartender on Monday was great but our bartender / waitress was not a good bartender. One ..."

Reviewed on Jul 25, 2026

Opens in a new windowCrowne Plaza Suffern - Mahwah by IHG
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
$116 nightly
The price is $137 total per night from Aug 2 to Aug 3
$137 total
Aug 2 - Aug 3
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will ...
"POOR BREAKFAST, REALLY UNSATISFYING POOL. WATER WAS NOT CLEAR AND ITWAS VERY HIGH CHLORINE CONCENTRATION ."

Reviewed on Jul 24, 2026

Opens in a new windowSleep Inn & Suites Middletown - Goshen
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
2 Bryle Place Chester NY
Fully refundable
$99 nightly
The price is $122 total per night from Aug 5 to Aug 6
$122 total
Aug 5 - Aug 6
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the ...
"Just ok for what I paid. And there was no tp in the room when we checked in."

Reviewed on Jul 26, 2026

Opens in a new windowHoliday Inn Express Hotel & Suites Chester by IHG
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $103 total per night from Aug 9 to Aug 10
$103 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Families will appreciate the onsite laundry ...
"Ice machine not working. A/C in room would then heat. Couldn’t maintain an even temp."

Reviewed on Jul 25, 2026

Opens in a new windowSpark by Hilton Fishkill
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $175 total per night from Jul 28 to Jul 29
$175 total
Jul 28 - Jul 29
Total with taxes and fees
A full-service spa and a restaurant are featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. There's ...
"We had a beautiful stay as always. Beautiful surroundings and we enjoyed our stay. We come back here often and always have a great time."

Reviewed on Jul 25, 2026

Opens in a new windowOverlook Lodge at Bear Mountain
LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

3 out of 5
1 LEGOLAND BLVD Goshen NY
$423 nightly
The price is $499 total per night from Jul 27 to Jul 28
$499 total
Jul 27 - Jul 28
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. There's fun for all ages with a playground and an arcade/game room. Enjoy the seasonal outdoor pool ...
"Clean and very nice. The food not so good. If booking through a third party parking is not included."

Reviewed on Jul 22, 2026

Opens in a new windowLEGOLAND Hotel NEW York
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
1289 Route 300 Newburgh NY
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $85 total per night from Jul 27 to Jul 28
$85 total
Jul 27 - Jul 28
Total with taxes and fees
A nightclub and a gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self ...
"This was one of the worst hotel experiences I've had. The stairways are carpeted, and parts of the carpet are loose, creating a safety hazard. They were also noticeably dirty. Unfortunately, the room was even worse. It smelled strongly of cigarette smoke along with another unpleasant odor that I ..."

Reviewed on Jul 25, 2026

Opens in a new windowRamada by Wyndham Newburgh/West Point
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4 out of 5
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $140 total per night from Aug 23 to Aug 24
$140 total
Aug 23 - Aug 24
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
Opens in a new windowDoubleTree by Hilton Hotel Nanuet
Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

2.5 out of 5
1 Sleep Way Monroe NY
Fully refundable
$113 nightly
The price is $127 total per night from Aug 4 to Aug 5
$127 total
Aug 4 - Aug 5
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour ...
Opens in a new windowSleep Inn & Suites Monroe - Woodbury
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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.

Chester Hotel & Travel Guide

So you are looking to spend some time in Newburgh? Need to reserve a place to stay in the Chester area? 3 hotels listed on Travelocity are situated within easy driving distance from the city centre.

The Holiday Inn Express Hotel & Suites Chester is the closest to the center of Chester and the sole Travelocity-listed accommodation option less than a short drive away.

You could also try the Minerals Hotel and the Caldwell House Bed & Breakfast. The Minerals Hotel is just 18 miles (29 kilometers) away from downtown Chester. The Caldwell House Bed & Breakfast, can be found just 9 miles (14 kilometers) away. The Peach Grove Inn and also the Hampton Inn Harriman Woodbury are two more Travelocity-listed options around Chester.

If you have time, you could travel to other parts of Hudson Valley. Spend time at Hudson Valley's historic bridges and open-air markets. Those drawn to nature should also make the time to enjoy its rivers, valleys and rolling hills. Popular activities in this pocket of United States of America include rock climbing.

Looking for more activities? You could spend the day enjoying Dia Beacon and Bannerman Castle, in Beacon, 19 miles (30 kilometers) to the northeast of Chester. When you get to Beacon, be sure to check out the The Roundhouse and Quality Inn & Suites. 15 miles (24 kilometers) to the east of Chester, you can also stay at West Point, which boasts the West Point Motel and FairBridge Inn & Suites at West Point. The United States Military Academy and West Point Museum are some more frequented places to visit when in West Point.

Simply because you are having a getaway, who says you can't indulge in your love for sport. Madison Square Garden is 45 miles (70 kilometers) to the south of Chester. Wise travelers that hope to find a hotel near the stadium can choose from the The St. Regis New York or the Mandarin Oriental, New York.

Stewart International Airport is a practical airport for those flying into Chester. It's located 14 miles (22 kilometers) from the heart of the city. For travelers who would find it convenient to find a base nearby, enquire about Four Points by Sheraton Newburgh Stewart Airport or Hudson Valley Hotel and Conference Center by Fairbridge.

Frequently asked questions

What are the top kid-friendly hotels in Chester?
Family vacations are where the best memories are made, but it's no secret that traveling with little ones can be challenging. These kid-friendly Chester hotels offer perks designed to keep guests of all ages comfortable and happy: Your entourage will love staying at 6 bedroom colonial house. A playground and free WiFi are a few of the things that help make this property a favorite. Alternatively, spend your Chester break at Holiday Inn Express Hotel & Suites Chester, an IHG Hotel. Take advantage of a swimming pool, complimentary breakfast and more here.
Where can I find cheap hotels in Chester?
At Travelocity you'll find really nice hotels in Chester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Chester rather than in Chester. We may find you even better rates, too.
How do I find the best Chester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Chester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Chester?
The cheapest hotel in Chester is $85. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Chester?
There are 1,054 hotels in Chester on Travelocity.
What are the best hotels in Chester?
Chester has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Chester for you!
When is the best time to visit Chester?
If you want the joy of a fun-filled trip in peak season, visit Chester during January, February and March. If you'd prefer the peace of off-season, book a stay during quieter months, such as October, November and December.
When is the cheapest time to stay in Chester?
Based on historic data is usually the cheapest month to visit Chester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Chester?
There are multiple hotels in Chester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Chester. We have plenty of kid-friendly hotels in Chester to choose from on Travelocity!
Why book a hotel in Chester through Travelocity?
Because we have the top hotels in Chester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Chester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Chester hotel reviews by fellow wanderers

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

5 out of 5
Posted 6 hours ago
Travelocity Verified Review
"The manager was very friendly. I would stay again."
A verified traveler stayed at Hampton Inn Harriman Woodbury
Hampton Inn Harriman Woodbury

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