Find hotels in Chester, NY from Rp1.419.474

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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, (1007)
"timely & courteous check-in; clean rooms; quiet environment; perfect location for our needs "
United States
Orlando
The price is Rp1.406.580
Rp1.661.523 total
includes taxes & fees
4 Jan - 5 Jan 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 Rp3.600.175
Rp4.072.719 total
includes taxes & fees
31 Dec - 1 Jan 2026
The Dominion House Bed & Breakfast

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, (801)
"Clean quiet and nice reception "
United States
Nick
The price is Rp1.373.090
Rp1.553.308 total
includes taxes & fees
11 Jan - 12 Jan 2026
Holiday Inn Express & Suites Montgomery by IHG

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1019)
"Great stay and room was very nice"
United States
Emmanuel
The price is Rp1.633.977
Rp2.011.836 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Harriman Woodbury

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.2 out of 10, Wonderful, (1003)
"Yes stay was pleasant "
United States
henry
The price is Rp1.565.658
Rp1.771.150 total
includes taxes & fees
3 Jan - 4 Jan 2026
Comfort Suites Fishkill near Interstate 84

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1007)
"The room was very clean, comfortable bed, good service and at a reasonable price."
Canada
DIMITRIOS
The price is Rp1.416.627
Rp1.602.559 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sleep Inn & Suites Monroe - Woodbury

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, (1004)
"Always stay here on my way through NY."
United States
Kathleen
The price is Rp1.494.491
Rp1.690.643 total
includes taxes & fees
3 Jan - 4 Jan 2026
Quality Inn & Suites Fishkill South near I-84

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1008)
"Clean room, friendly staff, good breakfast"
United States
Zuriber
The price is Rp1.716.363
Rp1.997.417 total
includes taxes & fees
11 Jan - 12 Jan 2026
DoubleTree by Hilton Hotel Nanuet

Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (959)
"Staff both during check in and out were great . Great stay ."
United States
david
The price is Rp1.657.253
Rp1.957.629 total
includes taxes & fees
9 Jan - 10 Jan 2026
Tru by Hilton Middletown

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport
2.5 star property
Newburgh
9.2 out of 10, Wonderful, (980)
"Excellent stay and I will be back! "
United States
Jawara
The price is Rp1.771.286
Rp2.092.331 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Newburgh Stewart Airport

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, (1003)
"Love it, everytime we come this is the place to stay"
United States
William
The price is Rp1.691.078
Rp1.913.116 total
includes taxes & fees
1 Jan - 2 Jan 2026
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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 Rp1.691.245
Rp2.082.346 total
includes taxes & fees
6 Jan - 7 Jan 2026
Fairfield Inn & Suites by Marriott Goshen Middletown

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, (1004)
"Very nice stay."
United States
Peter
The price is Rp1.507.050
Rp1.704.851 total
includes taxes & fees
24 Jan - 25 Jan 2026
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1005)
"Room was clean and staff was great!"
United States
Annemarie
The price is Rp1.209.826
Rp1.429.107 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn by Hilton Middletown

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG
3.5 star property
Suffern
8.8 out of 10, Excellent, (1007)
"Room was clean and staff was friendly. "
United States
Jose
The price is Rp1.841.950
Rp2.143.569 total
includes taxes & fees
27 Jan - 28 Jan 2026
Crowne Plaza Suffern - Mahwah by IHG

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1004)
"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 Rp1.992.655
Rp2.254.212 total
includes taxes & fees
1 Jan - 2 Jan 2026
Overlook Lodge at Bear Mountain

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (980)
"The shower pressure was very low, the room was small, and the soundproofing was poor."
China
Ting
The price is Rp1.431.028
Rp1.640.316 total
includes taxes & fees
12 Jan - 13 Jan 2026
Quality Inn near Mountain Creek

Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah
2.5 star property
Mahwah
8.8 out of 10, Excellent, (1429)
"Amazing hotel, felt safe for my family and I. Will recommend. "
United States
Brittney
The price is Rp1.908.595
Rp2.187.726 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Mahwah

Residence Inn by Marriott Fishkill

Residence Inn by Marriott Fishkill
3.0 star property
Fishkill
9.4 out of 10, Exceptional, (406)
"High marks to this property!! Staff, cleanliness, room layout all excellent!!"
United States
Ron
The price is Rp2.211.177
Rp2.501.393 total
includes taxes & fees
24 Jan - 25 Jan 2026
Residence Inn by Marriott Fishkill

Inn on the Hudson

Inn on the Hudson
2.0 star property
Peekskill
7.0 out of 10, Good, (1003)
"yes but the beds were not comfortable"
United States
Gene
The price is Rp1.490.305
Rp1.704.474 total
includes taxes & fees
4 Jan - 5 Jan 2026
Inn on the Hudson
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 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 Activities: Chester boasts a variety of attractions suitable for all ages, including resorts, batting cages, and archaeological digs.
  • Outdoor Adventures: Explore national and state parks, serene lakes, and urban parks, offering ample opportunities for outdoor pursuits.
  • Charming Accommodations: Enjoy a range of lodging options, from pet-friendly hotels to cosy agritourism properties, catering to diverse preferences.
  • Vibrant City Life: Experience the lively atmosphere of Chester, blending urban charm with natural beauty.
  • Nearby Adirondack Hamlets: Discover charming hamlets nearby, perfect for a picturesque autumn getaway.

Find great hotels near Chester

Discover the charming accommodation options in Chester, New York, perfect for all types of travellers. Whether you're seeking a pet-friendly hotel for a family getaway or a business-friendly stay with essential amenities, Chester offers a range of choices. From cosy agritourism properties to well-equipped hotels, you'll find the ideal lodging to enhance your visit. Experience the warm hospitality and unique character that Chester has to offer during your holiday.

  • Hampton Inn Harriman Woodbury: Experience a blend of comfort and convenience at the Hampton Inn Harriman Woodbury, located only 12.9km from Chester. This hotel is perfect for business travellers and those seeking a pet-friendly stay, welcoming pets with a flexible policy that includes variable fees and specific restrictions. The property proudly supports LGBTQIA travellers, ensuring an inclusive environment for all. Guests appreciate the modern amenities and thoughtful services that make every stay enjoyable, from complimentary breakfast to a well-equipped business centre.
  • The Crossroads Hotel, Newburgh: Situated 22.5km from Chester, The Crossroads Hotel offers a welcoming atmosphere with a strong focus on business travel and inclusivity for LGBTQIA guests. This 3-star hotel combines functionality with comfort, featuring well-appointed rooms that cater to the needs of modern travellers. With its strategic location, guests can easily explore nearby attractions while enjoying a restful retreat at the hotel, making it an excellent choice for both work and leisure.
  • Red Roof Inn & Suites Newburgh – Stewart Airport/West Point: Just 22.5km from Chester, the Red Roof Inn & Suites Newburgh is an ideal choice for families and business travellers alike. This hotel not only embraces LGBTQIA guests but also provides amenities specifically designed for families, such as complimentary cribs. Its proximity to Stewart Airport and West Point makes it a convenient option for those on the go. Guests appreciate the comfortable accommodations and the welcoming environment, making it a preferred choice for a hassle-free stay.

Where to stay near Chester

Chester, New York, offers a delightful blend of family-friendly attractions and vibrant city life, making it an ideal destination for a memorable vacation. Explore the charming Adirondack hamlets nearby, perfect for an autumn city break, or unwind in the beautiful surroundings of Chester itself. With a range of accommodations available, you can easily find a place that suits your budget and taste, ensuring a comfortable stay in this welcoming community.

  • Middletown: Situated 16.1km from Chester, Middletown is a vibrant city that offers a delightful blend of family-friendly activities and urban charm. Visitors are drawn to its entertainment-themed experiences, particularly during peak months such as April and the summer season. The city boasts an array of attractions, including a popular theme park and a scenic lake, making it an ideal destination for outdoor enthusiasts. Shopping aficionados will find bliss in its bustling shopping malls and centres, ensuring a fulfilling retail therapy experience.
  • Goshen: Just 6.4km from Chester, Goshen is another charming city that captivates tourists with its family-oriented atmosphere and entertainment offerings. Popular throughout the year, especially in March and July, the city is home to a variety of engaging activities. Visitors can explore its delightful shopping centres and resorts, perfect for a leisurely day out. The town also features a picturesque square and a theme park, providing ample opportunities for enjoyment and relaxation amidst its quaint surroundings.
  • Monroe: Located 8.0km from Chester, Monroe presents a unique mix of family, business, and city-themed experiences. Peak visitor months include June, July, and September, when the local ski resorts and shopping centres come alive with activity. The city's proximity to natural attractions like a stunning lake and mountains offers outdoor adventures for nature lovers. Additionally, Monroe's vibrant shopping scene ensures that visitors can indulge in a diverse range of retail options while enjoying the city's welcoming atmosphere.

Things to do in and around Chester

Chester offers a delightful blend of family-friendly activities and entertainment-themed attractions, making it an ideal destination for your holiday. Visitors can enjoy various options, including resorts, shopping centres, and shopping malls. Notable experiences include batting cages, intriguing archaeological digs, and the opportunity for memorable day trips, ensuring that there is something for everyone to enjoy during their stay in this charming town.

Shopping

In Chester, you can visit Harriman Plaza Shopping Center and Monroe Federal Plaza Shopping Center, both within 11.3km, offering a mix of family entertainment and city vibes. If you're up for a drive, Soons Orchards, located 11.3km away, provides a charming market atmosphere ideal for gifts and souvenirs.

Recreation

The Rock Sports Complex offers an energetic atmosphere with various sports activities, perfect for those seeking an active getaway. The Golf Club at Mansion Ridge, with its luxurious setting, promises a relaxing day of golfing. Meanwhile, Thomas Bull Memorial Park provides a tranquil environment for wellness and relaxation amidst nature.

Adventure

For thrilling motor racing, visit Orange County Fair Speedway, located 14.5km from Chester, where you can feel the adrenaline and excitement of the sport. Alternatively, enjoy the slopes at Mount Peter Ski Area, 12.9km away, perfect for skiing enthusiasts seeking adventure in a stunning winter landscape.

Nightlife

In Chester, Castle Fun Center offers an exhilarating arcade adventure atmosphere perfect for a fun night out. For a more romantic evening, the nearby Paramount Theatre and Ritz Theater provide captivating cultural experiences, both showcasing entertaining performances just a short distance away.

*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 for tourists. Enjoy free entry to attractions like Sterling Forest State Park and explore the town at no cost. For accommodation, consider visiting between January and March for lower prices, avoiding the busier August to October period. Tuesdays are typically the cheapest days to stay, while Saturdays are pricier. Use Expedia's search tool to filter by budget and location, and consider booking package deals that combine hotels, flights, and activities for additional savings.

  • 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: Utilise Expedia's search tool to refine your preferences, such as your budget, preferred location, and desired hotel type. To discover the best prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You may find that you can save money by combining your Chester hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions in and around Chester

Chester is an excellent destination for family-friendly vacations, offering a blend of entertainment and urban charm. Visitors can explore a variety of popular attractions, including national and state parks, serene lakes, and urban parks. These points of interest provide ample opportunities for outdoor activities, cultural experiences, and stunning scenery, making Chester a delightful spot for travellers seeking both adventure and relaxation.

  • Goosepond Mountain State Park: Experience the beauty of nature at Goosepond Mountain State Park, where outdoor enthusiasts can enjoy hiking trails, stunning vistas, and the thrill of adventure amidst picturesque scenery.
  • Algonquin Park: Located 25.7km away from Chester, Algonquin Park is a perfect family-friendly urban park, offering spacious green areas for picnics, playgrounds for children, and trails for leisurely strolls, all nestled within the city atmosphere.
  • National Purple Heart Hall of Honor: Just 20.9km from Chester, this military museum is dedicated to honouring the sacrifices of veterans. Explore its rich cultural exhibits that tell the poignant stories of bravery and honour associated with the Purple Heart.

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 journey to Chester, New York, you have several airport options. John F. Kennedy International Airport (JFK) is located 90.1km away, with nearby hotels including the 4-star TWA Hotel at JFK, just 483m from the airport, and the Allegria Hotel, 11.3km away. LaGuardia Airport (LGA) is 74.0km from Chester, offering luxurious stays like The Plaza, 8.0km away, and Hilton Club The Quin, 9.7km distant. Westchester County Airport (HPN) is the closest at 39.7km, with good options such as J House Greenwich, 11.3km away. Each hotel provides convenient access to their respective airports, ensuring a smooth travel experience.

Frequently asked questions

What's the best place to stay in Chester?
Based on our traveller 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 choices for your stay in 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 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 Museum Village. Additionally, you might want to add Goosepond Mountain State Park 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.