Find hotels in Chester, NY from AED 303

Start date: Check-in selected.
To Date
End date: Check-out
  • 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

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Compare 1,007 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 star property
Chester
8.6 out of 10, Excellent, (1009)
"Great for a quick stay 👍"
United States
Jerry
The price is AED 288
AED 340 total
includes taxes & fees
30 Nov - 1 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 AED 790
AED 893 total
includes taxes & fees
1 Dec - 2 Dec
The Dominion House Bed & Breakfast

DoubleTree by Hilton Hotel Nanuet

4.0 star property
Nanuet
8.8 out of 10, Excellent, (1009)
"Very clean very beautiful very good hospitality would stay again"
United States
Bobby
The price is AED 389
AED 452 total
includes taxes & fees
7 Dec - 8 Dec
DoubleTree by Hilton Hotel Nanuet

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1019)
"Parking was very easy, beautiful area, very nice staff"
United States
Elizabeth
The price is AED 385
AED 435 total
includes taxes & fees
3 Dec - 4 Dec
Overlook Lodge at Bear Mountain

The Abbey Inn & Spa

4.0 star property
Peekskill
9.2 out of 10, Wonderful, (223)
"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 AED 1,017
AED 1,331 total
includes taxes & fees
30 Nov - 1 Dec
The Abbey Inn & Spa

Inn on the Hudson

2.0 star property
Peekskill
6.8 out of 10, (1006)
"Always a pleasant place "
United States
Abner
The price is AED 327
AED 374 total
includes taxes & fees
30 Nov - 1 Dec
Inn on the Hudson

Sonesta Simply Suites Nanuet

2.5 star property
Nanuet
8.4 out of 10, Very Good, (1032)
"Great place"
United States
Andrea
The price is AED 406
AED 472 total
includes taxes & fees
8 Dec - 9 Dec
Sonesta Simply Suites Nanuet

Hampton Inn Nanuet

2.5 star property
Nanuet
7.8 out of 10, Good, (1005)
"Spotless room, clean quiet, good breakfast, friendly staff."
United States
Gayle A
The price is AED 408
AED 455 total
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, (1006)
"It was pleasant to stay "
United States
Nilsa
The price is AED 408
AED 475 total
includes taxes & fees
13 Dec - 14 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, (1008)
"Beautiful hotel, great breakfast!"
United States
Elaine
The price is AED 438
AED 501 total
includes taxes & fees
30 Nov - 1 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, (1013)
"One of the best Hotel in Rockland, everything was clean "
United States
Kenson
The price is AED 408
AED 475 total
includes taxes & fees
5 Dec - 6 Dec
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 AED 272
AED 303 total
includes taxes & fees
30 Nov - 1 Dec
Budget Motor Inn - Stony Point

Days Inn by Wyndham Nanuet / Spring Valley

2.0 star property
Nanuet
6.8 out of 10, (1002)
"Great stay"
United States
Deon Francine
The price is AED 372
AED 432 total
includes taxes & fees
30 Nov - 1 Dec
Days Inn by Wyndham Nanuet / Spring Valley

High Point Motel

2.0 star property
Sussex
9.0 out of 10, Wonderful, (97)
"Great place to stay"
United States
Bob
The price is AED 297
AED 332 total
includes taxes & fees
8 Dec - 9 Dec
High Point Motel

The Crossroads Hotel, Newburgh

3.0 star property
Newburgh
7.2 out of 10, Good, (689)
"Great Stay!"
United States
Charles
The price is AED 360
AED 426 total
includes taxes & fees
30 Nov - 1 Dec
The Crossroads Hotel, Newburgh

Element Spring Valley

3.0 star property
Spring Valley
8.8 out of 10, Excellent, (428)
"Staff, cleanliness, nice breakfast"
United States
Jesus
The price is AED 450
AED 523 total
includes taxes & fees
14 Dec - 15 Dec
Element Spring Valley

Sleep Inn & Suites Middletown - Goshen

2.5 star property
Middletown
8.6 out of 10, Excellent, (1004)
"Friendly staff, clean room and great breakfast "
United States
Janet
The price is AED 371
AED 439 total
includes taxes & fees
18 Dec - 19 Dec
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Monroe - Woodbury

2.5 star property
Monroe
9.4 out of 10, Exceptional, (1009)
"The best hotel in town"
United States
Yehuda
The price is AED 359
AED 406 total
includes taxes & fees
18 Dec - 19 Dec
Sleep Inn & Suites Monroe - Woodbury

Super 8 by Wyndham Mahwah

2.5 star property
Mahwah
7.4 out of 10, Good, (1004)
"Room was clean and staff was helpful "
United States
Berldwin
The price is AED 281
AED 322 total
includes taxes & fees
21 Dec - 22 Dec
Super 8 by Wyndham Mahwah

Fairfield Inn & Suites Mahwah

2.5 star property
Mahwah
8.2 out of 10, Very Good, (1003)
"Nice clean hotel would definitely stay again "
United States
Isaac
The price is AED 371
AED 425 total
includes taxes & fees
30 Nov - 1 Dec
Fairfield Inn & Suites Mahwah
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.

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels
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 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

Hotels in Chester with star-rating

Find out more about Chester

Top reasons to visit Chester

  • Family-Friendly Activities: Chester offers a variety of entertainment options suitable for all ages, making it perfect for family vacations.
  • Scenic Nature: Enjoy hiking and exploring national and state parks, as well as picturesque lakes and urban parks.
  • Local Culture: Experience the warmth of Chester's friendly locals and vibrant community events.
  • Charming Neighborhoods: Discover quaint neighborhoods that enhance the peaceful atmosphere of your getaway.
  • Diverse Accommodations: From budget-friendly to luxurious stays, Chester provides a range of hotel options for every traveler.

Find great hotels near Chester

Discover the charm of Chester, New York, with a variety of hotel accommodations designed for every type of traveler. Whether you're seeking a family-friendly experience, a pet-friendly stay, or a place equipped for business travel, Chester's hotels offer the perfect blend of comfort and convenience. Explore the best hotels in the area, read reviews, and make your vacation memorable in this picturesque destination.

  • Super 8 by Wyndham Middletown: A budget-friendly motel that offers a comfortable stay just 14.5km from Chester, Super 8 by Wyndham Middletown is perfect for travelers seeking convenience and affordability. Guests can unwind with entertainment options including premium TV channels, satellite TV, and a flat-screen television in their rooms. The property also features nearby outlet shopping for those looking to indulge in a little retail therapy. With its no-frills approach and essential amenities, this motel is a solid choice for a hassle-free getaway.
  • Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point: Ideal for families and business travelers alike, the Red Roof Inn & Suites is situated 22.5km from Chester and prides itself on creating an inclusive atmosphere for all guests, including LGBTQIA travelers. With complimentary cribs available for families, the property provides a comfortable stay that caters to the needs of all ages. The hotel is conveniently located near Stewart Airport and West Point, making it an excellent base for those exploring the area. Its welcoming environment and family-friendly amenities make it a popular choice.
  • Howard Johnson by Wyndham Newburgh/West Point: Situated 22.5km from Chester, Howard Johnson by Wyndham Newburgh/West Point is tailored for business travelers seeking a productive stay. The hotel offers essential business amenities, ensuring guests have everything they need for a successful trip. Its convenient location allows easy access to local attractions and corporate offices, making it a reliable choice for those on work assignments. With a focus on comfort and functionality, this hotel is designed to meet the needs of the modern business traveler.

Where to stay near Chester

Chester, New York, offers a delightful blend of family-friendly charm and vibrant local culture. Visitors can explore its quaint neighborhoods, enjoy the warm atmosphere created by friendly locals, and discover the best spots for entertainment and relaxation. With low crowds and a convenient location, Chester is perfect for those seeking a peaceful getaway while still being close to nearby attractions. Whether you're looking for budget options or a touch of luxury, Chester has something for everyone.

  • Middletown: Situated approximately 16.1km from Chester, Middletown is a vibrant city that offers a diverse travel experience. Known for its family-friendly atmosphere, it attracts visitors year-round, with peak seasons in April and June to July. Travelers can explore an array of entertainment options, including a bustling shopping mall and various resort facilities. Notably, the nearby theme park and scenic lake provide fantastic opportunities for outdoor activities and relaxation. Whether you're seeking a lively city experience or a day of fun with the family, Middletown has something for everyone.
  • Goshen: Only 6.4km from Chester, Goshen is a charming city that captures the essence of family and entertainment-themed adventures. This locale sees consistent traveler arrivals, with peak months in March, July, and September. Visitors can indulge in shopping at the local shopping center or enjoy leisure time at a resort. The vibrant modern square, along with the nearby theme park and tourist precinct, offers a delightful mix of activities for all ages. Goshen is perfect for those looking to immerse themselves in a welcoming community with plenty to explore.
  • Monroe: Just 8.0km from Chester, Monroe is a dynamic city that caters to family, business, and city-themed experiences. With a steady flow of visitors, particularly in June to July and September, Monroe is a hub for shopping and outdoor fun. Guests can enjoy the local shopping mall and ski facilities, while the nearby theme park, picturesque lake, and stunning mountain views offer ample opportunities for adventure. Monroe is ideal for travelers seeking a blend of urban excitement and natural beauty.

Things to do in and around Chester

Chester, New York, offers a family-friendly vacation with a blend of entertainment and city-themed activities. Explore popular attractions like resorts, shopping centers, and malls. Be sure to check out local event calendars, enjoy scenic sightseeing, participate in festive activities, and prepare for hiking adventures in the beautiful surrounding nature.

Shopping

In Chester, you can visit Monroe Federal Plaza Shopping Center, just 9.7km away, offering a family-friendly atmosphere. Soons Orchards, 11.3km away, features a charming market vibe. If you're up for a drive, Old Glory Mall Shopping Center is 12.9km away, providing entertainment and shopping options.

Recreation

The Rock Sports Complex in Chester offers an energetic atmosphere with various sports activities to engage in. The Golf Club at Mansion Ridge, a short drive away, provides a luxurious golfing experience, while Thomas Bull Memorial Park is perfect for wellness and relaxation, surrounded by nature.

Adventure

Experience the thrill of motorsports at Orange County Fair Speedway, located 14.5km from Chester, where the adrenaline of racing fills the air. For winter fun, head to Mount Peter Ski Area, 12.9km away, offering exciting skiing and snowboarding opportunities. Explore the scenic Continental Road Trailhead, also 12.9km from Chester, for outdoor adventures on beautiful trails.

Nightlife

For a fun night, visit Castle Fun Center for arcade games and family-friendly adventures. If you're in the mood for romance and culture, catch a show at Paramount Theatre or Ritz Theater, both offering captivating performances just a short drive from Chester.

*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 excellent savings for tourists with free entry to attractions like Sterling Forest State Park. To save on accommodation, plan your visit between January and March, when prices are lower, and consider staying on Tuesdays for the best rates. Utilize public transport to minimize travel costs, and explore Expedia for package deals that combine flights, hotels, and activities for extra savings. Remember to filter your search from lowest to highest price to find great deals and last-minute offers for your stay.

  • 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: Utilize Expedia’s search tool to narrow down your options based on your budget, preferred location, and desired hotel type. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • 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 in and around Chester

Chester, New York, is an ideal destination for family-friendly and entertainment-themed vacations. Visitors can explore a variety of attractions, including national and state parks, lakes, and urban parks. The area's points of interest offer a perfect blend of outdoor activities, cultural experiences, and scenic beauty, making it a delightful spot for travelers seeking adventure and relaxation amidst nature.

  • Bear Mountain State Park: Experience the breathtaking beauty of Bear Mountain State Park, located 24.1km from Chester. Enjoy hiking trails, scenic vistas, and outdoor adventures that highlight the park's natural charm. The park offers a perfect escape for nature lovers and thrill-seekers alike.
  • United States Military Academy: Located 22.5km from Chester, the United States Military Academy at West Point is a prestigious institution with rich history. Take a guided tour to explore its historic grounds, stunning architecture, and learn about the military traditions that shape future leaders.
  • Museum Village: Situated within Chester, Museum Village is a charming historic site that immerses visitors in local culture. Explore authentic 19th-century buildings and exhibits that bring history to life, offering a unique glimpse into the region's past.

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

When planning your trip to Chester, New York, you can choose from several major airports. John F. Kennedy International Airport (JFK) is 90.1km away, with nearby hotels like the 5-star Arlo Williamsburg and The William Vale, both 17.7km from the airport. Newark Liberty International Airport (EWR) is 75.6km away, offering luxury options such as The Dominick and The Beekman, both 14.5km from EWR. LaGuardia Airport (LGA) is the closest at 74.0km, featuring hotels like Virgin Hotels New York City and The Plaza, just 5 to 9.7km away. Each airport provides convenient transportation services to and from these hotels.

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 traveler reviews. See all available top hotels, or vacation rentals in Chester.
What's the top vacation rental in Chester?
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: Visitors like this Chester vacation home rental. It 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 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 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.
Where can I learn more about changing or cancelling my trip to Chester?
For more details about updating your trip to Chester or cancelling it, click here.
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.
Where is the best hotel to stay with easy access to The Rock Sports Complex?
Holiday Inn Express Hotel & Suites Chester, an IHG Hotel is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and an indoor pool. It's located just a short 0.8 mi (1.3 km) from The Rock Sports Complex. Other good options within 5 miles include Fairfield Inn & Suites by Marriott Goshen Middletown and NATURE'S NIRVANA FOR FAMILY AND FRIEND.
What about the best place to stay near Castle Fun Center?
One of the top choices for your stay is Holiday Inn Express Hotel & Suites Chester, an IHG Hotel, located a short 0.4 mi (0.6 km) from Castle Fun Center, and this hotel offers free breakfast and an indoor pool. Fairfield Inn & Suites by Marriott Goshen Middletown and Stagecoach Inn are two other good options within a few miles.
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 the best hotel near Stewart International Airport (SWF)?
Howard Johnson by Wyndham Newburgh is a popular hotel, featuring free breakfast and free WiFi. It's located a short 0.8 mi (1.2 km) from Stewart Intl. Airport. Other options within close proximity to the airport include Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport and Super 8 by Wyndham Newburgh/West Point Near Stewart Airport.
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 19 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 Goosepond Mountain State Park. Additionally, you might want to add Museum Village 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.

Explore a world of travel with Expedia