Chester Hotels

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Top 10 trending Chester hotels

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 star property
Chester
8.6 out of 10, Excellent, (1013)
"Great for a quick stay 👍"
United States
Jerry
The price is €98
includes taxes & fees
3 Dec - 4 Dec
Holiday Inn Express Hotel & Suites Chester by IHG

The Dominion House Bed & Breakfast

2.0 star property
Chester
9.2 out of 10, Wonderful, (233)
"Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY."
United States
Erek
The price is €210
includes taxes & fees
3 Dec - 4 Dec
The Dominion House Bed & Breakfast

DoubleTree by Hilton Hotel Nanuet

4.0 star property
Nanuet
8.8 out of 10, Excellent, (1016)
"Very clean very beautiful very good hospitality would stay again"
United States
Bobby
The price is €106
includes taxes & fees
14 Dec - 15 Dec
DoubleTree by Hilton Hotel Nanuet

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1023)
"Parking was very easy, beautiful area, very nice staff"
United States
Elizabeth
The price is €116
includes taxes & fees
4 Dec - 5 Dec
Overlook Lodge at Bear Mountain

The Abbey Inn & Spa

4.0 star property
Peekskill
9.2 out of 10, Wonderful, (224)
"The staff, the room, the restaurant and bar were all excellent. The Abby is a special place. Beautiful architecture, great art! Location can’t be beat. "
United States
Lya
The price is €318
includes taxes & fees
3 Dec - 4 Dec
The Abbey Inn & Spa

Inn on the Hudson

2.0 star property
Peekskill
6.8 out of 10, (1007)
"Always a pleasant place "
United States
Abner
The price is €88
includes taxes & fees
7 Dec - 8 Dec
Inn on the Hudson

Sonesta Simply Suites Nanuet

2.5 star property
Nanuet
8.2 out of 10, Very good, (1040)
"Great place"
United States
Andrea
The price is €111
includes taxes & fees
2 Dec - 3 Dec
Sonesta Simply Suites Nanuet

Hampton Inn Nanuet

2.5 star property
Nanuet
7.8 out of 10, Good, (1008)
"Spotless room, clean quiet, good breakfast, friendly staff."
United States
Gayle A
The price is €107
includes taxes & fees
7 Dec - 8 Dec
Hampton Inn Nanuet

Hilton Garden Inn Nanuet

3.0 star property
Nanuet
7.8 out of 10, Good, (1007)
"It was pleasant to stay "
United States
Nilsa
The price is €112
includes taxes & fees
12 Dec - 13 Dec
Hilton Garden Inn Nanuet

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

2.5 star property
Peekskill
9.2 out of 10, Wonderful, (1012)
"Beautiful hotel, great breakfast!"
United States
Elaine
The price is €118
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 star property
Suffern
8.8 out of 10, Excellent, (1020)
"One of the best Hotel in Rockland, everything was clean "
United States
Kenson
The price is €104
includes taxes & fees
1 Jan - 2 Jan 2026
Crowne Plaza Suffern - Mahwah by IHG

Budget Motor Inn - Stony Point

1.5 star property
Stony Point
4.8 out of 10, (473)
"I'm happy with my room"
United States
Ethan
The price is €57
includes taxes & fees
2 Dec - 3 Dec
Budget Motor Inn - Stony Point

Element Spring Valley

3.0 star property
Spring Valley
8.8 out of 10, Excellent, (429)
"Staff, cleanliness, nice breakfast"
United States
Jesus
The price is €123
includes taxes & fees
7 Dec - 8 Dec
Element Spring Valley

Days Inn by Wyndham Nanuet / Spring Valley

2.0 star property
Nanuet
6.8 out of 10, (1003)
"Great stay"
United States
Deon Francine
The price is €107
includes taxes & fees
15 Dec - 16 Dec
Days Inn by Wyndham Nanuet / Spring Valley

Sleep Inn & Suites Monroe - Woodbury

2.5 star property
Monroe
9.4 out of 10, Exceptional, (1013)
"The best hotel in town"
United States
Yehuda
The price is €85
includes taxes & fees
1 Jan - 2 Jan 2026
Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Middletown - Goshen

2.5 star property
Middletown
8.6 out of 10, Excellent, (1011)
"Friendly staff, clean room and great breakfast "
United States
Janet
The price is €103
includes taxes & fees
21 Dec - 22 Dec
Sleep Inn & Suites Middletown - Goshen

High Point Motel

2.0 star property
Sussex
9.0 out of 10, Wonderful, (99)
"Great place to stay"
United States
Bob
The price is €85
includes taxes & fees
2 Dec - 3 Dec
High Point Motel

The Crossroads Hotel, Newburgh

3.0 star property
Newburgh
7.2 out of 10, Good, (694)
"Great Stay!"
United States
Charles
The price is €100
includes taxes & fees
2 Dec - 3 Dec
The Crossroads Hotel, Newburgh

Super 8 by Wyndham Mahwah

2.5 star property
Mahwah
7.4 out of 10, Good, (1007)
"Room was clean and staff was helpful "
United States
Berldwin
The price is €74
includes taxes & fees
1 Jan - 2 Jan 2026
Super 8 by Wyndham Mahwah

Fairfield Inn & Suites Mahwah

2.5 star property
Mahwah
8.2 out of 10, Very good, (1004)
"Nice clean hotel would definitely stay again "
United States
Isaac
The price is €100
includes taxes & fees
7 Dec - 8 Dec
Fairfield Inn & Suites Mahwah
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Stay near popular Chester attractions

Learn more about Chester

Lace up your hiking boots and hit the trails at Goosepond Mountain State Park for stunning views. After working up an appetite, head to Castle Fun Centre for go-karts, mini-golf, and arcade games.

Black dirt region farm Chester New York

Top Chester Hotel Reviews

More cheap stays in Chester

Find out more about Chester

Top reasons to visit Chester

  • Family-Friendly Attractions: Chester offers a variety of activities suitable for all ages, ensuring a fun-filled holiday for families.
  • Stunning Natural Scenery: Visitors can enjoy the beauty of national parks and serene lakes, perfect for outdoor enthusiasts.
  • Vibrant Urban Life: The city boasts lively shopping centres and a charming atmosphere, ideal for a leisurely stroll.
  • Rich Cultural Experiences: Discover Chester's unique history and character through its attractions and local traditions.
  • Diverse Accommodation Options: From budget-friendly hotels to luxurious stays, Chester caters to every traveller's needs.

Find great hotels near Chester

Discover a range of delightful accommodations in Chester, New York, catering to every traveller's needs. From family-friendly hotels to pet-friendly options, you'll find suitable lodging to enhance your stay. Enjoy modern amenities like free Wi-Fi and accessible rooms, ensuring a comfortable experience whether you're on a business trip or a leisurely holiday. Explore unique agritourism properties or choose from popular hotel options like Aberdeen Hotels and Abode Chester for a memorable visit.

  • Super 8 by Wyndham Middletown: Located 14.5km from Chester, Super 8 by Wyndham Middletown offers a comfortable and affordable motel experience for travellers. With dining options like WrappedFood for breakfast, guests can kickstart their day with ease. The hotel features entertainment amenities including Premium TV Channels, Television, and Satellite TV, ensuring a pleasant stay. Nearby attractions include outlet shopping, perfect for those looking to indulge in some retail therapy. This property is ideal for visitors seeking simplicity without compromising on comfort.
  • Red Roof Inn & Suites Newburgh – Stewart Airport/West Point: Situated 22.5km from Chester, Red Roof Inn & Suites is a welcoming hotel renowned for its pet-friendly and LGBTQIA-inclusive environment. This property caters to business travellers with essential amenities such as a Business Centre and Meeting Room. With a flexible pet policy allowing dogs and cats, it ensures a homely atmosphere for all guests. The hotel is affiliated with LGBTQI travel guides, making it a unique choice for those seeking inclusivity during their stay.
  • Howard Johnson by Wyndham Newburgh/West Point: Also located 22.5km from Chester, Howard Johnson by Wyndham is tailored for business travellers seeking a productive stay. This hotel offers a range of services and facilities that cater specifically to the needs of professionals. Its strategic location near major business hubs makes it a convenient choice for corporate guests. With a focus on comfort and efficiency, this property ensures a seamless experience for those looking to balance work and leisure.

Where to stay near Chester

Chester, New York, offers a delightful blend of family-friendly attractions and vibrant city life. Explore the charming Amherst area, with its stunning gardens and welcoming atmosphere. Discover the rich history of the ancient city while enjoying the beauty of blue skies above. Whether you seek budget-friendly options or luxurious experiences, Chester and its surrounding regions cater to every traveller's desires, ensuring a memorable holiday for all.

  • Middletown: Situated 16.1km from Chester, Middletown is a vibrant city that offers a delightful mix of urban charm and family-friendly attractions. Visitors can enjoy a variety of entertainment options, including shopping centres and resorts. The peak travel seasons in April and from June to July see families flocking to the area to experience its exciting theme parks and picturesque lakes. With a lively tourist precinct and numerous dining establishments, Middletown promises an engaging travel experience for all ages.
  • Goshen: Just 6.4km away from Chester, Goshen is a quaint city known for its welcoming atmosphere and rich history. This charming destination sees a surge of visitors during March, July, and September, drawn by its family-oriented attractions and city-themed experiences. Goshen features a range of shopping centres and resorts, making it a great place for leisure and relaxation. The local attractions, including a modern square and nearby theme parks, enhance the travel experience, offering something for everyone to enjoy.
  • Monroe: Located 8.0km from Chester, Monroe is a bustling city that caters to families, business travellers, and adventure seekers alike. The peak times for visitors are during the summer months of June to July and in September. Monroe boasts a variety of shopping centres and resorts, making it an excellent destination for leisure. The surrounding area features beautiful lakes and mountains, as well as a popular theme park, providing ample opportunities for outdoor activities and exploration. This dynamic city ensures a memorable stay for all who visit.

Find the best attractions near Chester

Chester, New York, is an ideal destination for family and entertainment-themed holidays, offering a variety of attractions such as national parks, serene lakes, and urban parks. Visitors can immerse themselves in outdoor activities while enjoying the stunning scenery and rich cultural experiences available in and around the area. Whether you're seeking adventure or relaxation, Chester promises a memorable getaway for all.

  • United States Military Academy: Explore the prestigious United States Military Academy, known for its stunning architecture and rich history. This iconic institution offers guided tours that provide insight into the training of future leaders of the U.S. Army, set against a backdrop of beautiful landscapes along the Hudson River.
  • Bear Mountain State Park: Immerse yourself in the natural beauty of Bear Mountain State Park, where you can enjoy breathtaking views, hiking trails, and diverse wildlife. The park is perfect for outdoor enthusiasts seeking adventure amidst scenic vistas and tranquil environments.
  • Harness Racing Museum and Hall of Fame: Delve into the fascinating world of harness racing at this unique museum, where you can learn about the sport's history, view memorabilia, and enjoy interactive exhibits that celebrate the culture and excitement of horse racing.

Best time to go to Chester

The best time to visit Chester is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.0°F (-2.2°C)Light RainMostly SunnyAverageSlightly Low
February29.8°F (-1.2°C)Light RainMostly SunnySlightly LowSlightly Low
March37.4°F (3.0°C)Light RainMostly SunnyAverageSlightly Low
April48.7°F (9.3°C)Light RainMostly SunnyAverageAverage
May59.4°F (15.2°C)Light RainMostly SunnyAverageAverage
June67.6°F (19.8°C)Light RainMostly SunnySlightly HighAverage
July73.9°F (23.3°C)Light RainMostly SunnySlightly HighSlightly High
August72.0°F (22.2°C)Light RainMostly SunnyAverageSlightly High
September64.9°F (18.3°C)Light RainMostly SunnySlightly HighAverage
October54.0°F (12.2°C)Light RainMostly SunnyAverageSlightly High
November42.1°F (5.6°C)Light RainMostly SunnySlightly LowAverage
December34.2°F (1.2°C)Light RainMostly SunnySlightly LowAverage

The nearest major airports for your trip to Chester

When planning your journey to Chester, New York, you have several major airports to consider. John F. Kennedy International Airport (JFK) is situated 90.1km away, with luxurious hotel options like Arlo Williamsburg, The William Vale, and The Boro Hotel, all approximately 17.7km from the airport. Newark Liberty International Airport (EWR) is 75.6km from Chester, offering notable accommodations such as The Dominick, The Wall Street Hotel, and The Beekman, all about 14.5km away. Lastly, LaGuardia Airport (LGA) is 74.0km from Chester, with five-star options like Virgin Hotels New York City, The Mark, and The Carlyle, all around 5 to 9.7km from the airport.

Frequently asked questions

What's the best place to stay in Chester?
The Dominion House Bed & Breakfast is ranked highly by Expedia customers. This B&B offers free breakfast and an outdoor pool. Holiday Inn Express Hotel & Suites Chester by IHG is another top choice for your trip based on traveller reviews. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Chester offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and a coffee maker, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. See all vacation rentals in Chester.
If I need to cancel my hotel reservation in Chester, will I receive a refund?
Yes! You'll find that most room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
What is the favourite LGBTQ-friendly accommodation in Chester?
Holiday Inn Express Hotel & Suites Chester by IHG is a top LGBTQ-friendly hotel that features free breakfast and free Wi-Fi. The Dominion House Bed & Breakfast is another good option for your trip. See all available hotels listed as LGBTQ-friendly in Chester.
What are some accommodation options with pools in Chester?
Holiday Inn Express Hotel & Suites Chester by IHG is a top hotel with a pool, free on-the-go breakfast and free WiFi. View all hotels with pools in Chester.
What is staying in Chester like?
Visitors to Chester will definitely enjoy the shopping and restaurants. Tourists can also enjoy the city's ski areas and coffee shops. In Chester, there are 18 hotels and other accommodation options to choose from. Find out more about Chester.
What are the top places to visit in Chester?
Favourite places to visit include Castle Fun Center, The Rock Sports Complex and Goosepond Mountain State Park. Additionally, you might want to add Museum Village to your itinerary. Take a look at what more there is to see and do in Expedia's Chester guide.
What's the seasonal weather like in Chester?
The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Chester are January, February, March and April, with each month seeing an average of 16 cm of snowfall.

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