Find hotels in Chester, NY from $66

Top reasons to visit Chester

• Outdoor Adventures: Chester is perfect for hiking, exploring national and state parks, and enjoying beautiful lakes.
• Family-Friendly Attractions: The area offers a variety of entertainment options suitable for all ages.
• Vibrant Events: Chester hosts numerous festive events throughout the year, adding local charm to your visit.
• Charming Atmosphere: Experience the serene landscapes and friendly community, ideal for relaxation.
• Diverse Accommodations: Chester provides a range of lodging options, from pet-friendly to family-oriented stays.

Find great hotels near Chester

Discover a variety of lodging options in Chester, New York, catering to all types of travelers. Whether you're seeking pet-friendly accommodations, family-friendly experiences, or business-focused amenities, Chester has something for everyone. Explore the best hotels in the area to find the perfect fit for your vacation, complete with helpful hotel reviews to guide your choice.

• Super 8 by Wyndham Middletown: Super 8 by Wyndham Middletown offers a cozy and budget-friendly motel experience, located 9 miles away from Chester. This property caters to travelers looking for a straightforward stay without sacrificing comfort. Guests can kick-start their day with a complimentary breakfast and unwind while enjoying entertainment options like satellite TV and premium channels. Nearby outlets provide easy shopping opportunities, making it a convenient choice for leisure travelers and families alike.
• Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point: Located 14 miles from Chester, Red Roof Inn & Suites is an inclusive and family-friendly hotel that warmly welcomes LGBTQIA guests and their furry friends. This property features a variety of amenities designed for families, including free cribs, and a pet-friendly policy that allows dogs and cats. The hotel’s commitment to ensuring a comfortable stay for all types of travelers makes it an ideal choice for those seeking a relaxed environment with a personal touch.
• Howard Johnson by Wyndham Newburgh/West Point: Situated 14 miles from Chester, Howard Johnson by Wyndham is perfect for business travelers seeking a productive stay. This hotel offers essential services and facilities tailored for corporate needs, ensuring guests can conduct business efficiently while enjoying a comfortable atmosphere. With its convenient location and business-friendly amenities, it’s a top choice for professionals looking to balance work and leisure during their visit.

Where to stay near Chester

Chester, New York, offers a delightful blend of charm and convenience for families and leisure travelers alike. Explore the serene landscapes and friendly atmosphere while enjoying low crowds in this picturesque city. Discover the best spots for relaxation, outdoor activities, and local dining. Nearby attractions provide a budget-friendly escape, ensuring a memorable vacation experience filled with friendly people and a welcoming vibe. Chester is truly a hidden gem waiting to be explored.

• Middletown: Located approximately 10 miles from Chester, Middletown is a vibrant city that offers a blend of family-friendly activities and entertainment options. Visitors can enjoy a variety of attractions including a theme park and beautiful lakes, making it ideal for those looking to create lasting memories. The shopping centers and malls cater to retail enthusiasts, while the city's resorts provide a relaxing getaway. With peak travel seasons in April and from June to July, it’s a great spot to experience city life intertwined with leisure.
• Goshen: Just 4 miles from Chester, Goshen is a charming city that draws travelers seeking family-oriented and entertainment-themed experiences. With a modern square at its heart, visitors can explore shops and enjoy the bustling atmosphere. The town’s proximity to a theme park and various resorts adds to its appeal, especially during peak travel times in March and July. Whether you're looking for a quick shopping trip or a fun family day out, Goshen offers a delightful mix of activities.
• Monroe: Situated 5 miles away from Chester, Monroe is a lively city that caters to both families and business travelers. Its shopping centers and malls provide ample opportunities for retail therapy, while the nearby theme park, lake, and mountains offer exciting recreational activities. The travel experience peaks in the summer months, particularly from June to July and September, making it a popular destination. Whether you're on a family vacation or a business trip, Monroe has something for everyone.

Things to do in and around Chester

Chester, New York, is a fantastic destination for family-friendly vacations and entertainment seekers. Visitors can enjoy a range of activities, including exploring local resorts, shopping at the mall center, and participating in festive events. Don’t miss the vibrant event calendars and typical sightseeing opportunities that showcase the area’s charm. For outdoor enthusiasts, hiking essentials are readily available, making Chester a perfect blend of relaxation and adventure.

Shopping

In Chester, you can explore Monroe Federal Plaza Shopping Center, only 6 miles away, for a vibrant shopping experience. Soons Orchards, 7 miles away, offers local produce and unique gifts. Old Glory Mall Shopping Center, 8 miles away, combines entertainment and shopping for the whole family.

Recreation

Experience the energetic atmosphere at The Rock Sports Complex, where you can engage in various sports activities. For a touch of luxury, visit The Golf Club at Mansion Ridge, offering exquisite golfing experiences. Unwind at Thomas Bull Memorial Park, a perfect spot for relaxation and rejuvenation in nature.

Adventure

Experience the thrill of motor racing at Orange County Fair Speedway, located 9 miles from Chester, where adrenaline and excitement reign. Enjoy skiing at Mount Peter Ski Area, 8 miles away, or explore the scenic Continental Road Trailhead, also 8 miles from Chester, perfect for outdoor adventures.

Nightlife

Experience the vibrant nightlife in Chester at Castle Fun Center, where adventure awaits in their arcade. For a touch of culture and romance, catch a show at Paramount Theatre or Ritz Theater, both offering family-friendly entertainment just a short drive away.

Booking tips and Expedia advantages for Chester

Chester, New York, is a budget-friendly destination with plenty of free activities, like exploring Sterling Forest State Park. To save on accommodations, plan your trip between January and March when prices are lower, and aim for a Tuesday stay for the best rates. Utilize Expedia to find the best hotel deals by filtering prices from lowest to highest, and consider booking a package to combine your hotel, flights, and activities for additional savings. Join the One Key membership for exclusive discounts and earn OneKeyCash for future stays.

• 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: Utilize Expedia's search tool to refine your preferences, such as your budget, desired location, and preferred 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 by purchasing an Expedia package.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Chester

Chester, New York, is an ideal destination for family fun and entertainment-themed vacations. Visitors can explore a variety of attractions, including national and state parks, beautiful lakes, and urban parks. These points of interest offer outdoor adventures, cultural experiences, and stunning scenery, catering to travelers seeking both relaxation and excitement. No matter your interests, Chester promises a memorable getaway for everyone.

• United States Military Academy: Located 14 miles from Chester, this prestigious military academy offers a glimpse into American military history and training. Visitors can explore the stunning campus, take guided tours, and admire the picturesque views of the Hudson River.
• Bear Mountain State Park: Just 15 miles away, Bear Mountain State Park is a haven for outdoor enthusiasts. With its scenic hiking trails, breathtaking views, and opportunities for picnicking and wildlife watching, it's perfect for adventure seekers and nature lovers alike.
• Harness Racing Museum and Hall of Fame: Situated only 4 miles from Chester, this museum celebrates the rich history of harness racing. Enjoy interactive exhibits and engaging displays that showcase the sport's culture and significance in American history.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	28.0°F (-2.2°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	29.8°F (-1.2°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
March	37.4°F (3.0°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	48.7°F (9.3°C)	Light Rain	Mostly Sunny	Average	Average
May	59.4°F (15.2°C)	Light Rain	Mostly Sunny	Average	Average
June	67.6°F (19.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	73.9°F (23.3°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	72.0°F (22.2°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	64.9°F (18.3°C)	Light Rain	Mostly Sunny	Slightly High	Average
October	54.0°F (12.2°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	42.1°F (5.6°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	34.2°F (1.2°C)	Light Rain	Mostly Sunny	Slightly Low	Average

The nearest major airports for your trip to Chester

When planning your visit to Chester, New York, you have several major airports to choose from. John F. Kennedy International Airport (JFK) is located 56 miles away, with excellent nearby hotels like Arlo Williamsburg and The William Vale, both 11 miles from JFK. Newark Liberty International Airport (EWR) is 47 miles away, featuring luxury accommodations such as The Dominick and The Wall Street Hotel, both 9 miles from EWR. LaGuardia Airport (LGA) is the closest at 46 miles, with upscale options like Virgin Hotels New York City and The Mark, both just 6 miles from LGA. Each airport offers convenient access to Chester for a smooth travel experience.