Chester Hotels

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Our top choices for Chester hotels

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, (1002)
"timely & courteous check-in; clean rooms; quiet environment; perfect location for our needs "
United States
Orlando
The price is P7,353
P8,686 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Holiday Inn Express Hotel & Suites Chester by IHG

The Dominion House Bed & Breakfast

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 P12,647
P14,307 total
includes taxes & fees
Jan 12 - Jan 13, 2026
The Dominion House Bed & Breakfast

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1000)
"Room was clean and staff was great!"
United States
Annemarie
The price is P4,700
P5,552 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hampton Inn by Hilton Middletown

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (599)
"Excellent, clean, comfortable stay on a stormy night. Great staff."
United States
Paul
The price is P5,824
P6,581 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Days Inn by Wyndham Wurtsboro

LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.8 out of 10, Excellent, (33)
"We are having a great time at the hotel!!!"
United States
Ziwei
The price is P11,201
P20,382 total
includes taxes & fees
Jan 2 - Jan 3, 2026
LEGOLAND Hotel NEW York

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG
3.5 star property
Suffern
8.8 out of 10, Excellent, (1001)
"Clean rooms, comfortable bed, modern amenities, friendly staff, lots of parking "
United States
Derick
The price is P6,473
P7,533 total
includes taxes & fees
Jan 28 - Jan 29, 2026
Crowne Plaza Suffern - Mahwah by IHG

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1000)
"The room was very clean, comfortable bed, good service and at a reasonable price."
Canada
DIMITRIOS
The price is P4,702
P5,319 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Sleep Inn & Suites Monroe - Woodbury

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (982)
"Good breakfast, and everything was clean in a great room. "
United States
Steven
The price is P5,035
P5,771 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Quality Inn near Mountain Creek

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
2.5 star property
Goshen
8.8 out of 10, Excellent, (1001)
"Rooms were clean and as expected. Bed was a bit soft for our taste, but acceptable. Breakfast options were routine, scrambled eggs, bacon or sausage on alternating days, oatmeal, waffles, bagel, toast, English muffins... Pleasant and helpful staff, smooth check-in and check-out. Overall a pleasant place."
United States
Joon
The price is P6,177
P7,605 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Fairfield Inn & Suites by Marriott Goshen Middletown

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, (802)
"Clean quiet and nice reception "
United States
Nick
The price is P4,824
P5,457 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Holiday Inn Express & Suites Montgomery by IHG

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, (1007)
"Superb place to stay."
United States
Denessy
The price is P5,347
P6,048 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.2 out of 10, Wonderful, (999)
"Yes stay was pleasant "
United States
henry
The price is P5,500
P6,222 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Comfort Suites Fishkill near Interstate 84

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1020)
"Easy check in, clean room, very good breakfast."
United States
Robert
The price is P5,740
P7,067 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hampton Inn Harriman Woodbury

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
7.2 out of 10, Good, (20)
"Good place to rest your head for a night "
United States
Dennis J
The price is P5,258
P5,948 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Spark by Hilton Fishkill

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1016)
"Clean room, staff was very nice."
United States
Jonathan
The price is P6,029
P7,017 total
includes taxes & fees
Jan 11 - Jan 12, 2026
DoubleTree by Hilton Hotel Nanuet

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1006)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
The price is P7,000
P7,919 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Overlook Lodge at Bear Mountain

Inn on the Hudson

Inn on the Hudson
2.0 star property
Peekskill
7.0 out of 10, Good, (1001)
"The location was very convenient. There is not a lot available in Peekskill and this place was very close to where we were going. The room was well cleaned and cared for the only drawback was that the heating unit was very, very noisy."
United States
Shelley
The price is P5,235
P5,988 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Inn on the Hudson

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, (1001)
"Always stay here on my way through NY."
United States
Kathleen
The price is P5,250
P5,939 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Quality Inn & Suites Fishkill South near I-84

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport
2.5 star property
Newburgh
9.2 out of 10, Wonderful, (982)
"Clean hotel, good breakfast choices and space for eating."
United States
Morgan
The price is P6,225
P7,353 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Hampton Inn & Suites Newburgh Stewart Airport

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, (1000)
"Great customer service and breakfast was excellent "
United States
Dennis
The price is P5,294
P5,989 total
includes taxes & fees
Jan 24 - Jan 25, 2026
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
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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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 Center 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

  • Scenic Natural Beauty: Chester boasts picturesque landscapes, perfect for nature lovers and outdoor enthusiasts.
  • Family-Friendly Activities: A range of entertainment-themed attractions caters to families, ensuring fun for all ages.
  • Charming Accommodations: Diverse lodging options, from family hotels to agritourism properties, provide a comfortable stay.
  • Rich Local Culture: Explore quaint streets and vibrant local events that highlight Chester's unique character.
  • Outdoor Adventures: With hiking essentials readily available, Chester is ideal for those seeking adventure amidst nature.

Find great hotels near Chester

Chester, New York, offers a delightful array of accommodation options, ideal for every traveller. From family-friendly hotels to charming agritourism properties, you’ll find suitable lodging whether you’re on a business trip or enjoying a weekend getaway. With pet-friendly options and excellent amenities, Chester's hotels cater to diverse needs. Explore the best hotels in the area and read reviews to ensure a memorable stay in this picturesque locale.

  • Super 8 by Wyndham Middletown: Nestled 14.5km from Chester, Super 8 by Wyndham Middletown is a comfortable motel that caters to budget-conscious travellers seeking convenience. This property stands out for its entertainment options, including Television, Satellite TV, and Premium TV Channels, ensuring guests can unwind after a day of exploration. Nearby, guests can indulge in retail therapy at local outlets, making it an ideal choice for those who appreciate a blend of relaxation and shopping.
  • Red Roof Inn & Suites Newburgh – Stewart Airport/West Point: Located 22.5km from Chester, this inviting hotel is perfect for families and LGBTQIA-friendly travellers. With a pet-friendly policy, it welcomes dogs and cats, ensuring that your furry companions can join in on the vacation fun. The property offers complimentary cribs for families with young children, while its affiliation with LGBTQI travel guides adds an inclusive touch. The atmosphere is warm and welcoming, making it an excellent base for those seeking a family-oriented getaway.
  • Howard Johnson by Wyndham Newburgh/West Point: Just 22.5km from Chester, Howard Johnson by Wyndham Newburgh is tailored for business travellers. This hotel provides a tranquil environment for professionals looking to balance work and leisure during their stay. With essential amenities and comfortable accommodations, guests can enjoy a productive stay while being close to key business hubs. The property’s focus on business travel ensures that all your professional needs are met during your visit.

Where to stay near Chester

Chester, New York, offers a charming escape for families and couples alike, with a friendly atmosphere and low crowds for a relaxing stay. Explore the quaint streets and discover delightful spots that embody the town's unique character. Nearby regions provide a mix of budget and luxury experiences, ensuring there's something for everyone. Whether you’re seeking entertainment or a peaceful retreat, Chester’s charm and convenient location make it an ideal destination for your vacation.

  • Middletown: Situated approximately 16.1km from Chester, Middletown is a vibrant city that offers a delightful mix of family-friendly activities and urban experiences. Visitors can enjoy a variety of entertainment options, including a well-known theme park and a bustling shopping mall. The city's charm is accentuated by its picturesque lake and tourist precinct, perfect for leisurely strolls and family outings. The peak travel months of April and June to July draw in numerous tourists eager to explore Middletown’s resorts and shopping centres.
  • Goshen: Located just 6.4km from Chester, Goshen is a quaint city that welcomes families and entertainment seekers alike. Known for its lively atmosphere, Goshen peaks in visitor numbers during March, July, and September. Here, you can discover a charming blend of modern squares and a variety of shopping venues. The local attractions, including a theme park and a vibrant tourist precinct, make it an ideal spot for families looking to create memorable experiences. The city’s welcoming vibe ensures that every visitor feels right at home.
  • Monroe: Monroe lies a mere 8.0km from Chester and presents a unique blend of city and business themes, making it a great destination for families and corporate travellers. With visitor numbers peaking in June to July and September, Monroe offers a vibrant shopping mall and easy access to outdoor activities like skiing in the winter months. The proximity to a theme park, scenic lakes, and nearby mountains adds to the allure, providing a diverse range of experiences for every type of traveller.

Things to do in and around Chester

Chester offers a delightful mix of family-friendly and entertainment-themed activities, making it an ideal vacation destination. Visitors can enjoy resorts, shopping centres, and malls, while also exploring event calendars for local happenings. Typical sightseeing includes picturesque landscapes and festive activities throughout the year. For those who enjoy the outdoors, hiking essentials are readily available, making it perfect for nature enthusiasts.

Shopping

The nearest shopping destination is Monroe Federal Plaza Shopping Center, located 9.7km from Chester, offering a family-friendly atmosphere. Soons Orchards, a public market 11.3km away, provides a vibrant city vibe. If you're up for a drive, visit Old Glory Mall Shopping Center, situated 12.9km from Chester.

Recreation

The Rock Sports Complex in Chester offers an energetic atmosphere with various sports activities to engage in. A short drive away, The Golf Club at Mansion Ridge provides a luxurious golfing experience amidst picturesque landscapes. Meanwhile, Thomas Bull Memorial Park invites you to relax and rejuvenate in a serene natural environment.

Adventure

Experience the thrill of racing at Orange County Fair Speedway, located 14.5km from Chester, where adrenaline and excitement await. For winter sports enthusiasts, Mount Peter Ski Area, 12.9km away, offers fantastic skiing opportunities. Explore the outdoor beauty at Continental Road Trailhead, also 12.9km from Chester, perfect for adventurous hikes.

Nightlife

Experience the vibrant nightlife in Chester by visiting Castle Fun Center for exciting arcade adventures. For a touch of romance and culture, catch a show at the Paramount Theatre, located 16.1km away, or the Ritz Theater, just 25.7km from Chester, both offering superb entertainment options.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Chester

Chester, New York, offers various ways to save money during your visit. Enjoy free entry to attractions like Sterling Forest State Park, and consider travelling during the cheaper months of January to March, with Tuesdays being the most affordable days for accommodation. Use Expedia to compare hotel rates and find eco-friendly options. Bundling your hotel stay with flights and activities can also yield significant savings. For transportation, utilise public transport where possible to keep costs down while exploring this charming town.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chester are January to March, where the prices are slightly lower. This is in comparison to August to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chester is Tuesday. The most expensive day to stay in Chester is Saturday.
  • Find cheap hotels on Expedia: Expedia’s search tool enables you to specify your budget, desired location, and other preferences. You can organise your results to display prices in ascending order, allowing you to view the most affordable hotels first. Additionally, you have the option to refine your search by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that you can book.
  • Consider bundling your trip: You can save money by combining your hotel stay in Chester with your flights and activities through an Expedia package.

Find the best attractions near Chester

Chester is ideal for family and entertainment-themed holidays, offering a variety of attractions such as national and state parks, lakes, and urban parks. Visitors can enjoy outdoor activities, cultural experiences, and picturesque scenery, making it a perfect destination for those seeking relaxation and adventure. Whether you're exploring the natural beauty or indulging in local culture, Chester provides a delightful escape for all travellers.

  • Charles J. Everett Memorial: This poignant monument, located 6.4km from Chester, offers a deep cultural experience. Visitors can reflect on the significance of the memorial while enjoying the tranquil surroundings, making it a perfect spot for contemplation.
  • Touro College of Osteopathic Medicine: Situated 14.5km away, this modern institution exudes a lively city vibe. It is an impressive example of contemporary architecture and provides insight into the field of osteopathic medicine, making it an interesting visit for those keen on education.
  • Ochs Orchard: Just 16.1km from Chester, Ochs Orchard is a delightful farm experience. Visitors can enjoy picking fresh fruits, exploring the scenic landscape, and indulging in homemade treats at the farm store, perfect for a wholesome day out.

Best time to go to Chester

The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, 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 HighAverage
August72.0°F (22.2°C)Light RainMostly SunnyAverageSlightly High
September64.9°F (18.3°C)Light RainMostly SunnySlightly HighSlightly High
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

For your visit to Chester, New York, you can fly into three major airports. John F. Kennedy International Airport (JFK) is situated 90.1km away, with nearby hotels like The William Vale and The Boro Hotel, both 17.7km from JFK. Newark Liberty International Airport (EWR), located 75.6km from Chester, offers luxury options such as The Dominick and The Beekman, both 14.5km away. Lastly, LaGuardia Airport (LGA) is 74.0km from Chester, with excellent accommodations like Virgin Hotels New York City and The Plaza, both within 9.7km. All hotels provide convenient access to their respective airports for a smooth travel experience.

Frequently asked questions

What's the best place to stay in Chester?
Based on our traveler data, Holiday Inn Express Hotel & Suites Chester by IHG is one of the top choices for your stay. This hotel offers free breakfast and an indoor pool. Other good options for your trip to the area are DoubleTree by Hilton Hotel Nanuet and Sonesta Simply Suites Nanuet. See all available top hotels, or vacation rentals in Chester.
If I need to cancel my hotel reservation in Chester, will I receive a refund?
Yes, you'll find most hotel bookings are refundable if you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, you might be able to still 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 favorite LGBTQ-friendly place to stay in Chester?
Holiday Inn Express Hotel & Suites Chester by IHG is a top LGBTQ-friendly hotel that features free breakfast and free WiFi. 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 accommodations 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 are sure to enjoy the shopping and restaurants. Tourists can also enjoy the city's ski areas and coffeehouses. In Chester, there are 18 hotels and other accommodations to choose from. Find out more about Chester.
What are the top places to visit in Chester?
Favorite places to visit include Castle Fun Center, The Rock Sports Complex, and Museum Village. Additionally, you might want to add Goosepond Mountain State Park to your itinerary. Check out what more 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 temp of 70°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Chester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.