Chester Hotels

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

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, (1,000 reviews)
"We have been several times during the past few years the hotel is in very good condition and the coffee is really good available 24 hours a day the breakfast has several choices that are good the rooms are clean the A/C and heat work great overall great place to stay we come sometimes for a quick weekend getaway from New York City will continue to come back. Great local diner and restaurants."
United States
Kenneth
The price is €119
includes taxes & fees
16 Apr - 17 Apr
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 reviews)
"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 €206
includes taxes & fees
20 Apr - 21 Apr
The Dominion House Bed & Breakfast

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,047 reviews)
"Wonderful staff, clean and perfect for family, business or leisure stay. And budget friendly."
United States
Jawanda
The price is €97
includes taxes & fees
29 Apr - 30 Apr
Sleep Inn & Suites Monroe - Woodbury

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very good, (34 reviews)
"The hotel is new and clean"
United States
FENGMING
The price is €112
includes taxes & fees
23 Apr - 24 Apr
Comfort Suites Central Valley - Woodbury

High Point Motel

High Point Motel
2.0 star property
Sussex
9.2 out of 10, Wonderful, (123 reviews)
"Amazing easy check in/out and very kind staff. Had a wonderful stay, thank you! "
United States
Amanda
The price is €83
includes taxes & fees
29 Apr - 30 Apr
High Point Motel

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1,005 reviews)
"Amazing stay with great amenities!"
United States
Audrey
The price is €126
includes taxes & fees
10 May - 11 May
Overlook Lodge at Bear Mountain

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,000 reviews)
"It was a beautiful experience. Clean and 5 star service. The staff so friendly and helpful. Peaceful fun experience. "
United States
Amanda
The price is €93
includes taxes & fees
29 Apr - 30 Apr
Hampton Inn by Hilton Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
3.0 star property
Goshen
8.8 out of 10, Excellent, (1,000 reviews)
"Amazing staff Great breakfast Clean quiet rooms"
United States
R
The price is €123
includes taxes & fees
6 May - 7 May
Fairfield Inn & Suites by Marriott Goshen Middletown

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, (1,003 reviews)
"Great overall stay, nice restaurant beside hotel"
Canada
Dale
The price is €83
includes taxes & fees
3 May - 4 May
Quality Inn & Suites Fishkill South near I-84

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.6 out of 10, Excellent, (1,014 reviews)
"Great stay!!! "
United States
diana
The price is €101
includes taxes & fees
30 Apr - 1 May
Courtyard by Marriott Middletown Goshen

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, (846 reviews)
"Easy check in and beautiful room"
United States
CORETHA
The price is €96
includes taxes & fees
26 Apr - 27 Apr
Holiday Inn Express & Suites Montgomery by IHG

Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (997 reviews)
"Friendly staff and clean rooms"
United States
Magaly
The price is €94
includes taxes & fees
29 Apr - 30 Apr
Tru by Hilton Middletown

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,004 reviews)
"Best Hotel in area so far 😁 "
United States
Debi
The price is €106
includes taxes & fees
27 Apr - 28 Apr
Sleep Inn & Suites Middletown - Goshen

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
8.0 out of 10, Very good, (64 reviews)
"The place was spotless and the staff were very friendly. The bed was so comfortable lovely stay "
United States
sharon
The price is €96
includes taxes & fees
4 May - 5 May
Spark by Hilton Fishkill

The Hamlet Inn at Warwick

The Hamlet Inn at Warwick
2.5 star property
Warwick
7.6 out of 10, Good, (156 reviews)
"good accommodations "
United States
Alejandro
The price is €91
includes taxes & fees
16 Apr - 17 Apr
The Hamlet Inn at Warwick

Appalachian Motel

Appalachian Motel
2.0 star property
Vernon
7.6 out of 10, Good, (528 reviews)
"It's a very pleasant, comfortable place to stay with very nice inn keepers. The rooms are very clean and spacious. The views around the motel are beautiful...and you are very close to wonderful hiking trails and ski resorts."
United States
Colleen
The price is €66
includes taxes & fees
16 Apr - 17 Apr
Appalachian Motel

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,088 reviews)
"Clean, quiet and great breakfast."
United States
Dawn
The price is €133
includes taxes & fees
26 Apr - 27 Apr
Hampton Inn Harriman Woodbury

West Point Motel

West Point Motel
2.5 star property
Highland Falls
8.6 out of 10, Excellent, (686 reviews)
"Room was clean, staff was courteous and very good location "
United States
Georgina
The price is €104
includes taxes & fees
29 Apr - 30 Apr
West Point Motel

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (1,003 reviews)
"A lot to do over there, good for a whole weekend, or even more. Had great time. "
United States
illay
The price is €90
includes taxes & fees
6 May - 7 May
Quality Inn near Mountain Creek

Americas Best Value Inn at Central Valley-Woodbury

Americas Best Value Inn at Central Valley-Woodbury
2.0 star property
Central Valley
7.2 out of 10, Good, (1,004 reviews)
"Old "
United States
Roxana
The price is €89
includes taxes & fees
23 Apr - 24 Apr
Americas Best Value Inn at Central Valley-Woodbury
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.
Save an average of 15% on thousands of hotels when you're signed in

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.

Things to do in and around Chester

Chester offers a delightful blend of family-friendly activities and urban charm, making it an ideal destination for a memorable holiday. Visitors can explore its vibrant shopping centres and enjoy the comforts of local resorts. For those seeking a bit of sightseeing, Chester provides an array of attractions that showcase its unique character and history, ensuring a well-rounded experience for all.

Shopping

If you're up for a drive, you can visit Monroe Federal Plaza Shopping Center, 9.7km from Chester, and enjoy its lively atmosphere. Soons Orchards, 11.3km away, offers a charming public market experience. Old Glory Mall Shopping Center, located 12.9km from Chester, provides a mix of entertainment and shopping.

Recreation

The Rock Sports Complex in Chester offers a vibrant atmosphere for sports enthusiasts, perfect for active recreation. Just 9.7km away, The Golf Club at Mansion Ridge invites you to indulge in luxury while enjoying scenic views. Meanwhile, Thomas Bull Memorial Park, located 12.9km from Chester, provides serene spaces for relaxation and wellness.

Adventure

Experience the thrill of motor racing at Orange County Fair Speedway, located 14.5km from Chester, where adrenaline and speed meet. For winter sports enthusiasts, the Mount Peter Ski Area, 12.9km away, offers excellent skiing opportunities. Alternatively, the Continental Road Trailhead, also 12.9km from Chester, invites you to explore its scenic outdoor trails.

Nightlife

In Chester, the Castle Fun Center offers vibrant arcade adventures for a lively evening. Nearby, the Paramount Theatre and Ritz Theater provide cultural and romantic experiences, showcasing diverse entertainment that suits families and couples alike, perfect for a memorable night out.

*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 during your visit. Enjoy free entry to attractions like Sterling Forest State Park and take advantage of affordable public transport options. To save on accommodation, consider visiting between January and March, when prices are lower, and aim to book your stay on a Tuesday for the best rates. Utilise Expedia’s tools to filter for budget-friendly hotels, and consider booking a package that combines flights, hotels, and activities for additional savings. Look for eco-certified options to support sustainable travel while keeping costs down.

  • 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 July to August and 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 the type of hotel you desire. For instance, selecting the Eco-certified option will present you with sustainable and environmentally friendly hotels currently available. To discover the most affordable prices and offers, arrange the price filter from low to high.
  • Consider bundling your trip: You can save some money by combining your hotel reservation in Chester with your flights and activities by opting for an Expedia package.

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?
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.
What are some of the best holiday rentals that Chester has to offer?
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9: This holiday home rental outside of Chester is located on a lake, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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 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.

Explore a world of travel with Expedia