Chester Hotels

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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, (1,000 reviews)
"timely & courteous check-in; clean rooms; quiet environment; perfect location for our needs "
United States
Orlando
The price is €91
includes taxes & fees
22 Jan - 23 Jan
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 €209
includes taxes & fees
20 Jan - 21 Jan
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, (1,005 reviews)
"The room was very clean, comfortable bed, good service and at a reasonable price."
Canada
DIMITRIOS
The price is €79
includes taxes & fees
12 Feb - 13 Feb
Sleep Inn & Suites Monroe - Woodbury

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)
"The stone lodges are cute and cozy and the staff were quick and helpful if you needed anything. Great for a short stay at a reasonable price."
United States
Judith
The price is €116
includes taxes & fees
21 Jan - 22 Jan
Overlook Lodge at Bear Mountain

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, (813 reviews)
"The staff was great! The room was clean and the breakfast was excellent."
Canada
Joey
The price is €86
includes taxes & fees
18 Jan - 19 Jan
Holiday Inn Express & Suites Montgomery by IHG

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, (1,001 reviews)
"Good low-cost hotel with decent continental breakfast."
United States
Nancy
The price is €89
includes taxes & fees
23 Jan - 24 Jan
Quality Inn & Suites Fishkill South near I-84

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1,031 reviews)
"Nice clean hotel with friendly staff. "
United States
michelle
The price is €93
includes taxes & fees
1 Feb - 2 Feb
DoubleTree by Hilton Hotel Nanuet

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,000 reviews)
"Clean Rooms, clean hotel overall. Plenty of parking."
United States
KenNETH
The price is €82
includes taxes & fees
29 Jan - 30 Jan
Hampton Inn by Hilton Middletown

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
7.2 out of 10, Good, (21 reviews)
"Nice clean rooms. Updated by Hilton. Well priced, good value "
United States
Lewis
The price is €87
includes taxes & fees
23 Jan - 24 Jan
Spark by Hilton Fishkill

Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (966 reviews)
"Was a nice stay for a week"
United States
Laura
The price is €87
includes taxes & fees
26 Jan - 27 Jan
Tru by Hilton Middletown

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
10.0 out of 10, Exceptional, (2 reviews)
" Desde nuestra llegada, tuvimos una experiencia maravillosa en este magnífico hotel nuevo. La atención de todos y cada uno de los colaboradores fue excepcional, pero quiero destacar especialmente a Ángel, quien nos trató de una manera increíble. Gracias a su amabilidad y dedicación, realmente nos sentimos como en casa. Recomiendo ampliamente este hotel. Sin duda, un lugar maravilloso para hospedarse. Nos íbamos a quedar 2 noches y nos quedamos 3. "
Mexico
JUVENTINO
The price is €98
includes taxes & fees
15 Feb - 16 Feb
Comfort Suites Central Valley - Woodbury

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
2.5 star property
Goshen
8.8 out of 10, Excellent, (1,001 reviews)
"Great place to stay when you’re in need of relaxation and some family time!"
United States
Cynthia
The price is €98
includes taxes & fees
1 Feb - 2 Feb
Fairfield Inn & Suites by Marriott Goshen Middletown

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG
3.5 star property
Suffern
8.8 out of 10, Excellent, (1,002 reviews)
"Great staff and clean room. "
United States
Jordon
The price is €112
includes taxes & fees
23 Jan - 24 Jan
Crowne Plaza Suffern - Mahwah by IHG

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (146 reviews)
"Had a great stay at the the Borland House Inn a historical setting in a cute town with wonderful staff and a delicious breakfast"
United States
Deborah
Borland House Inn

Holiday Inn Express Ramsey-Mahwah by IHG

Holiday Inn Express Ramsey-Mahwah by IHG
2.5 star property
Ramsey
9.2 out of 10, Wonderful, (1,002 reviews)
"Best spot to book"
United States
Oscar
The price is €117
includes taxes & fees
17 Jan - 18 Jan
Holiday Inn Express Ramsey-Mahwah by IHG

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (989 reviews)
"Good breakfast, and everything was clean in a great room. "
United States
Steven
The price is €82
includes taxes & fees
28 Jan - 29 Jan
Quality Inn near Mountain Creek

Sussex Motel

Sussex Motel
2.5 star property
Sussex
8.8 out of 10, Excellent, (375 reviews)
"Perfect for the price. Nice personel."
United States
Adam
The price is €76
includes taxes & fees
25 Jan - 26 Jan
Sussex Motel

The Thayer Hotel at West Point

The Thayer Hotel at West Point
3.5 star property
West Point
9.0 out of 10, Wonderful, (681 reviews)
"Location was great & staying at a historic hotel was delightful."
United States
Bobby
The price is €153
includes taxes & fees
18 Jan - 19 Jan
The Thayer Hotel at West Point

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, (1,022 reviews)
"Superb place to stay."
United States
Denessy
The price is €96
includes taxes & fees
18 Jan - 19 Jan
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Inn on the Hudson

Inn on the Hudson
2.0 star property
Peekskill
7.0 out of 10, Good, (1,001 reviews)
"The staff was really welcoming!"
United States
Devis
The price is €87
includes taxes & fees
18 Jan - 19 Jan
Inn on the Hudson
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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 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?
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Chester 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 an electric kettle, so that 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 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 Goosepond Mountain State Park. Additionally, you might want to add Museum Village 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.

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