Find hotels in Chester, NY from $100

Top reasons to visit Chester

• Scenic Outdoor Adventures: Chester boasts beautiful national and state parks, perfect for hiking, picnicking, and enjoying nature.
• Family-Friendly Activities: The area offers numerous attractions that cater to families, ensuring fun for all ages.
• Charming Neighborhoods: Explore picturesque neighborhoods that showcase Chester's natural beauty and charm.
• Vibrant Nightlife: Enjoy a lively nightlife scene with various entertainment options for adults.
• Comfortable Accommodations: Chester provides a range of inviting hotels suitable for families, pets, and business travelers.

Find great hotels near Chester

Discover a range of inviting accommodations in Chester, New York, perfect for every traveler. From family-friendly options to pet-friendly stays, you'll find hotels that cater to both leisure and business needs. Explore the best hotels in Chester, where comfort meets convenience, ensuring a memorable vacation experience for all visitors.

• Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point: A budget-friendly hotel with a guest rating of 8.4, Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point is located 13 miles from Chester. This property is perfect for families and business travelers seeking a comfortable and pet-friendly stay. The hotel features family amenities, including complimentary cribs for the little ones. With a policy that welcomes pets, you can bring your furry friends along for your vacation. Enjoy a hassle-free experience with a range of services tailored for both children and pets.
• Super 8 by Wyndham Middletown: A budget-friendly motel located 9 miles from Chester, Super 8 by Wyndham Middletown is an excellent choice for those looking for straightforward accommodations. Guests can enjoy entertainment options such as satellite TV, television, and premium TV channels. The property is conveniently located near shopping outlets, making it easy for guests to explore the local area. With its focus on value and comfort, this motel provides everything you need for a pleasant stay without breaking the bank.
• Hampton Inn Harriman Woodbury: With a remarkable guest rating of 9.2, Hampton Inn Harriman Woodbury is a budget-friendly option located 8 miles from Chester. This hotel caters to both business travelers and pet owners, offering a welcoming atmosphere. It features a flexible pet policy, allowing you to bring your pets along with a variable fee. Known for its cleanliness and friendly service, the hotel provides a comfortable environment for relaxation after a day of exploring the area. Guests appreciate the thoughtful amenities and convenient location.

Where to stay near Chester

Chester, New York, offers a delightful blend of family-friendly activities and vibrant city life. Explore picturesque neighborhoods and top attractions that highlight the area's natural beauty and charm. Enjoy a lively nightlife scene, or unwind in the serene surroundings. With a welcoming atmosphere and options for every budget, Chester provides a perfect getaway for entertainment seekers and families alike. Discover the unique vibes of this charming city and its nearby regions for an unforgettable vacation experience.

• Middletown: Located 10 miles from Chester, Middletown is a vibrant city that offers a blend of family-friendly activities and urban experiences. With a consistent flow of visitors year-round, the city sees peak travel during the months of April through July. Travelers flock to Middletown for its entertainment options, including a variety of resorts and shopping centers. Local highlights include a lively theme park and a picturesque tourist precinct, perfect for leisurely strolls and family outings.
• Goshen: Just 4 miles away from Chester, Goshen is another charming city known for its family-oriented atmosphere and entertainment offerings. With visitor numbers peaking in March, July, and September, the city remains an appealing destination throughout the year. Here, you'll find excellent shopping centers and a welcoming resort scene. Notable attractions include a fun-filled theme park and a quaint tourist precinct, making it an ideal spot for family adventures and leisure.
• Monroe: Situated 5 miles from Chester, Monroe is a lively city that caters to families and business travelers alike. The city experiences a surge in visitors during the summer months of June and July, as well as September. Monroe boasts a variety of shopping centers and ski facilities, making it a popular destination for those seeking both retail therapy and outdoor fun. Nearby, you can enjoy the beauty of a local lake and explore scenic mountain areas, perfect for hiking and relaxation.

Things to do near Chester

Chester, New York, offers a delightful mix of family-friendly and entertainment-themed activities. You can enjoy a relaxing stay at local resorts, indulge in shopping at various centers and malls, and create unforgettable memories during family reunions. With ample sightseeing opportunities, Chester is a perfect destination for a well-rounded vacation that caters to all interests.

Shopping

In Chester, you can explore local shops for unique gifts and souvenirs. If you're up for a drive, head to the Woodbury Common Premium Outlets for a variety of brand-name stores or visit the nearby Galleria at Crystal Run for a larger shopping experience.

Recreation

The Golf Club at Mansion Ridge, located 6 miles from Chester, offers a luxurious retreat with picturesque views and a serene atmosphere. Enjoy a round of golf or relax at the clubhouse, all while soaking in the exclusive country club vibes perfect for a rejuvenating getaway.

Adventure

In Chester, explore the breathtaking landscapes at Lake Minnewaska State Park with hiking and biking trails. Experience thrilling water sports like kayaking and paddleboarding on the nearby Hudson River, or enjoy a heart-pounding zip line adventure at the local adventure park for an unforgettable day outdoors.

Nightlife

In Chester, New York, the nightlife offers a cozy atmosphere with local bars like The Stonehouse and The Barn. Enjoy live music, craft beers, and friendly conversation, while nearby, the scenic views of the Hudson River enhance your evening experience.

Booking tips and Expedia advantages for Chester

• 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: Expedia's search tool enables you to specify your budget, preferred destination, and additional preferences. You can arrange your search results by price, starting from the lowest, to easily find the most affordable hotel options. Additionally, you have the option to narrow your search by hotel category; for instance, selecting the Eco-certified filter will display sustainable and environmentally-friendly hotels that you can book.
• Consider bundling your trip: You can save money by combining your hotel stay in Chester with your flights and activities through an Expedia package deal.

Find the best attractions in and around Chester

Chester, New York, offers a delightful vacation for families and city enthusiasts alike, featuring a mix of outdoor adventures and cultural experiences. Visitors can explore scenic national and state parks, enjoy the tranquility of local lakes, and relax in urban parks. With a variety of attractions catering to those seeking nature, culture, and stunning landscapes, Chester is an ideal destination for travelers looking to unwind and explore.

• Museum Village: Step back in time at Museum Village, a charming historic village in Chester. This immersive experience showcases 19th-century life with authentic buildings, artifacts, and engaging exhibits that reflect the rich culture and history of the region.
• Bear Mountain State Park: Located 15 miles from Chester, Bear Mountain State Park is a breathtaking natural retreat. With stunning scenery, hiking trails, and outdoor adventures, it's perfect for those looking to explore the great outdoors and enjoy activities like picnicking and wildlife watching.
• Storm King Art Center: Just 12 miles from Chester, Storm King Art Center is a remarkable outdoor sculpture park. Visitors can wander through beautifully landscaped grounds while admiring large-scale contemporary artworks set against a backdrop of rolling hills, making it a unique cultural experience.

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.

The nearest major airports for your trip to Chester

For your visit to Chester, NY, you can fly into three major airports. John F. Kennedy International Airport (JFK) is located 56 miles away, with luxury options like the 5-star Arlo Williamsburg and The William Vale nearby. Newark Liberty International Airport (EWR) is 47 miles away, featuring top hotels such as The Dominick and Four Seasons Hotel New York Downtown, both 9 miles from the airport. LaGuardia Airport (LGA) is 46 miles from Chester, with excellent accommodations like The Plaza and The Pierre, both 5 miles away, offering convenient transportation services. Each airport provides various hotel options to enhance your travel experience.