Find hotels in Chester, NY from AED 242

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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, (1,001 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 AED 466
AED 551 total
includes taxes & fees
31 Mar - 1 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 AED 790
AED 893 total
includes taxes & fees
6 Apr - 7 Apr
The Dominion House Bed & Breakfast

High Point Motel

High Point Motel
2.0 star property
Sussex
9.2 out of 10, Wonderful, (121 reviews)
"Amazing easy check in/out and very kind staff. Had a wonderful stay, thank you! "
United States
Amanda
The price is AED 265
AED 296 total
includes taxes & fees
6 Apr - 7 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, (1,000 reviews)
"Great staff and clean rooms. Beautiful views."
United States
Renee
The price is AED 393
AED 445 total
includes taxes & fees
6 Apr - 7 Apr
Overlook Lodge at Bear Mountain

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.2 out of 10, Very Good, (25 reviews)
"The hotel is new and clean"
United States
FENGMING
The price is AED 372
AED 457 total
includes taxes & fees
26 Apr - 27 Apr
Comfort Suites Central Valley - Woodbury

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (157 reviews)
"What a wonderful experience staying at the Borland House is! With the quaint, homey feeling of the whole house, to the kindness of the staff. Your stay will absolutely be lovely. Ample towels are provided for the private, spacious bathroom. Very comfortable bedding and well appointed decorations are in the bedroom. I was in the Hummingbird Suite. I could see myself living there, it just had everything I needed. I look forward to visiting again in the future!"
United States
Elizabeth
The price is AED 376
AED 438 total
includes taxes & fees
29 Mar - 30 Mar
Borland House Inn

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (612 reviews)
"Everything was clean. "
United States
John
The price is AED 331
AED 374 total
includes taxes & fees
29 Mar - 30 Mar
Days Inn by Wyndham Wurtsboro

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 AED 418
AED 515 total
includes taxes & fees
2 Apr - 3 Apr
Fairfield Inn & Suites by Marriott Goshen Middletown

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.6 out of 10, Excellent, (1,010 reviews)
"Great stay!!! "
United States
diana
The price is AED 400
AED 473 total
includes taxes & fees
29 Mar - 30 Mar
Courtyard by Marriott Middletown Goshen

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 AED 365
AED 431 total
includes taxes & fees
14 Apr - 15 Apr
Hampton Inn by Hilton Middletown

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,001 reviews)
"Best Hotel in area so far 😁 "
United States
Debi
The price is AED 384
AED 453 total
includes taxes & fees
29 Mar - 30 Mar
Sleep Inn & Suites Middletown - Goshen

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (1,000 reviews)
"A lot to do over there, good for a whole weekend, or even more. Had great time. "
United States
illay
The price is AED 330
AED 379 total
includes taxes & fees
9 Apr - 10 Apr
Quality Inn near Mountain Creek

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, (837 reviews)
"The staff was great! The room was clean and the breakfast was excellent."
Canada
Joey
The price is AED 393
AED 445 total
includes taxes & fees
29 Mar - 30 Mar
Holiday Inn Express & Suites Montgomery by IHG

Rolling Hills Motel

Rolling Hills Motel
2.0 star property
Sussex
8.6 out of 10, Excellent, (205 reviews)
"Great local spot. Recently updated "
United States
Steve
The price is AED 305
AED 340 total
includes taxes & fees
29 Mar - 30 Mar
Rolling Hills Motel

The Hamlet Inn at Warwick

The Hamlet Inn at Warwick
2.5 star property
Warwick
7.6 out of 10, Good, (154 reviews)
"good accommodations "
United States
Alejandro
The price is AED 312
AED 353 total
includes taxes & fees
29 Mar - 30 Mar
The Hamlet Inn at Warwick

Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is AED 606
AED 1,130 total
includes taxes & fees
31 Mar - 1 Apr
Hike & Fish: Outdoor Retreat Near Trails

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, (1,003 reviews)
"Superb place to stay."
United States
Denessy
The price is AED 364
AED 411 total
includes taxes & fees
29 Mar - 30 Mar
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (987 reviews)
"Best hotel in town. Clean clean smoke free hotel "
United States
David
The price is AED 465
AED 550 total
includes taxes & fees
1 Apr - 2 Apr
La Quinta Inn & Suites by Wyndham Middletown-Goshen

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport
2.5 star property
Newburgh
9.2 out of 10, Wonderful, (1,001 reviews)
"Wonderful accommodations!!"
United States
Roxanne
The price is AED 419
AED 495 total
includes taxes & fees
19 Apr - 20 Apr
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,073 reviews)
"Hotel was very clean and well maintained "
United States
Stephen
The price is AED 419
AED 516 total
includes taxes & fees
19 Apr - 20 Apr
Hampton Inn Harriman Woodbury
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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

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?
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.
What's the top vacation rental in Chester?
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9: Visitors like this Chester vacation home rental. It is located on a lake and has a patio, a barbecue grill, 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 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 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 17 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.