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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)
"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 £104
includes taxes & fees
16 Apr - 17 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 £179
includes taxes & fees
20 Apr - 21 Apr
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, (1,047 reviews)
"Wonderful staff, clean and perfect for family, business or leisure stay. And budget friendly."
United States
Jawanda
The price is £84
includes taxes & fees
23 Apr - 24 Apr
Sleep Inn & Suites Monroe - Woodbury

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very good, (34 reviews)
"The hotel is new and clean"
United States
FENGMING
The price is £97
includes taxes & fees
23 Apr - 24 Apr
Comfort Suites Central Valley - Woodbury

High Point Motel

High Point Motel
2.0 star property
Sussex
9.2 out of 10, Wonderful, (123 reviews)
"Amazing easy check in/out and very kind staff. Had a wonderful stay, thank you! "
United States
Amanda
The price is £72
includes taxes & fees
29 Apr - 30 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, (1,001 reviews)
"Amazing stay with great amenities!"
United States
Audrey
The price is £93
includes taxes & fees
10 May - 11 May
Overlook Lodge at Bear Mountain

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 £80
includes taxes & fees
29 Apr - 30 Apr
Hampton Inn by Hilton Middletown

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 £100
includes taxes & fees
29 Apr - 30 Apr
Fairfield Inn & Suites by Marriott Goshen Middletown

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, (1,003 reviews)
"Great overall stay, nice restaurant beside hotel"
Canada
Dale
The price is £73
includes taxes & fees
3 May - 4 May
Quality Inn & Suites Fishkill South near I-84

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.6 out of 10, Excellent, (1,014 reviews)
"Great stay!!! "
United States
diana
The price is £95
includes taxes & fees
19 Apr - 20 Apr
Courtyard by Marriott Middletown Goshen

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, (846 reviews)
"Easy check in and beautiful room"
United States
CORETHA
The price is £83
includes taxes & fees
26 Apr - 27 Apr
Holiday Inn Express & Suites Montgomery by IHG

Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (997 reviews)
"Friendly staff and clean rooms"
United States
Magaly
The price is £82
includes taxes & fees
29 Apr - 30 Apr
Tru by Hilton Middletown

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,004 reviews)
"Best Hotel in area so far 😁 "
United States
Debi
The price is £93
includes taxes & fees
28 Apr - 29 Apr
Sleep Inn & Suites Middletown - Goshen

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
8.0 out of 10, Very good, (64 reviews)
"The place was spotless and the staff were very friendly. The bed was so comfortable lovely stay "
United States
sharon
The price is £85
includes taxes & fees
23 Apr - 24 Apr
Spark by Hilton Fishkill

The Hamlet Inn at Warwick

The Hamlet Inn at Warwick
2.5 star property
Warwick
7.6 out of 10, Good, (156 reviews)
"good accommodations "
United States
Alejandro
The price is £79
includes taxes & fees
19 Apr - 20 Apr
The Hamlet Inn at Warwick

Appalachian Motel

Appalachian Motel
2.0 star property
Vernon
7.6 out of 10, Good, (528 reviews)
"It's a very pleasant, comfortable place to stay with very nice inn keepers. The rooms are very clean and spacious. The views around the motel are beautiful...and you are very close to wonderful hiking trails and ski resorts."
United States
Colleen
The price is £57
includes taxes & fees
19 Apr - 20 Apr
Appalachian Motel

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,088 reviews)
"Clean, quiet and great breakfast."
United States
Dawn
The price is £116
includes taxes & fees
26 Apr - 27 Apr
Hampton Inn Harriman Woodbury

West Point Motel

West Point Motel
2.5 star property
Highland Falls
8.6 out of 10, Excellent, (686 reviews)
"Room was clean, staff was courteous and very good location "
United States
Georgina
The price is £91
includes taxes & fees
29 Apr - 30 Apr
West Point Motel

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (1,003 reviews)
"A lot to do over there, good for a whole weekend, or even more. Had great time. "
United States
illay
The price is £78
includes taxes & fees
4 May - 5 May
Quality Inn near Mountain Creek

Americas Best Value Inn at Central Valley-Woodbury

Americas Best Value Inn at Central Valley-Woodbury
2.0 star property
Central Valley
7.2 out of 10, Good, (1,004 reviews)
"Old "
United States
Roxana
The price is £74
includes taxes & fees
19 Apr - 20 Apr
Americas Best Value Inn at Central Valley-Woodbury
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.
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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

  • Stunning Outdoor Adventures: Explore beautiful national and state parks, picturesque lakes, and urban parks, perfect for nature enthusiasts.
  • Family-Friendly Attractions: Chester is packed with activities suitable for all ages, ensuring fun for the entire family.
  • Vibrant Shopping Experiences: Indulge in retail therapy at local shopping centres and malls, offering a wide range of options.
  • Warm Local Hospitality: Enjoy the charm and friendliness of the locals, enhancing your travel experience.
  • Diverse Accommodation Options: Choose from family-friendly hotels to luxury stays, catering to all types of travellers.

Find great hotels near Chester

Discover the charm of Chester, New York, with a variety of accommodation options that cater to every type of traveller. From family-friendly hotels to pet-friendly lodgings, the area offers a warm welcome for all. Whether you're seeking a business-themed stay or a relaxing getaway, Chester's hotels promise comfort and convenience, ensuring a delightful experience during your visit.

  • Super 8 by Wyndham Middletown: A convenient and budget-friendly lodging option, Super 8 by Wyndham Middletown is situated a mere 5.6km from Chester. This motel is ideal for travellers seeking a straightforward stay with essential amenities. Guests can start their day with complimentary breakfast options available on weekdays and weekends, including wrapped food for those on the go. The property boasts entertainment features such as premium TV channels, satellite TV, and a television in each room. With nearby outlet shopping, it's perfect for those looking to explore local attractions.
  • Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point: Located 8.7km from Chester, the Red Roof Inn & Suites Newburgh offers a welcoming atmosphere for families and business travellers alike. This hotel prides itself on being LGBTQIA-friendly and provides a selection of amenities tailored for business needs, including a meeting room and business centre. Families will appreciate the complimentary cribs available for younger guests. With its commitment to inclusivity and comfort, this property is a fantastic choice for diverse groups looking for a pleasant stay near the scenic Hudson Valley.
  • Howard Johnson by Wyndham Newburgh/West Point: Positioned 8.7km from Chester, the Howard Johnson by Wyndham Newburgh is an excellent choice for business-minded travellers. This hotel features a range of facilities designed to support corporate needs, ensuring a productive stay. With a focus on comfort and convenience, guests can take advantage of spacious accommodations and essential amenities, making it a suitable base for those visiting the West Point area or conducting business in Newburgh.

Where to stay near Chester

Chester, New York, offers a delightful blend of family-friendly attractions and vibrant city life. Discover the picturesque scenery as you explore nearby towns and enjoy the warm hospitality of the locals. Ideal for both budget-conscious travellers and those seeking luxury, Chester serves as a perfect base to experience the charm of New York City and its popular destinations. From entertainment to relaxation, this friendly city promises a memorable getaway for all.

  • Middletown: Situated approximately 6.2km from Chester, Middletown is a vibrant city offering a mix of family-friendly entertainment and urban experiences. While its visitor numbers remain fairly consistent throughout the year, the peak months of April and June to July see an influx of tourists eager to explore its array of attractions. From shopping centres to resorts, there's something for everyone. Local highlights include a lively theme park and picturesque lakes, perfect for a day out with family or friends. With its bustling atmosphere, Middletown invites you to immerse yourself in a truly enjoyable city-themed experience.
  • Goshen: Located a mere 2.5km from Chester, Goshen is a charming city that draws visitors year-round, with notable peaks in March, July, and September. Known for its family-friendly vibe and entertainment options, Goshen boasts a range of shopping centres and resorts. The city is also home to a delightful tourist precinct and a vibrant town square, making it an excellent spot for leisurely strolls and dining experiences. Whether you're looking to shop or simply enjoy the local culture, Goshen offers a welcoming atmosphere and unique attractions that are sure to delight.
  • Monroe: Just 3.1km from Chester, Monroe is a city that combines business and leisure, appealing to a diverse range of travellers. The peak visitor months of June to July and September highlight its attractiveness as a destination. Popular for its shopping malls and resorts, Monroe also features stunning natural landmarks, including lakes and mountains, making it perfect for outdoor enthusiasts. With a family-oriented vibe and a variety of activities on offer, Monroe provides a balanced travel experience that caters to both relaxation and adventure.

Things to do in and around Chester

Chester offers a delightful mix of family-friendly activities and city-themed attractions. Visitors can enjoy a relaxing stay at local resorts, explore vibrant shopping centres, and indulge in retail therapy at the shopping mall. With its variety of entertainment options, Chester is an ideal destination for a memorable holiday experience.

Shopping

For a delightful shopping experience in Chester, visit Monroe Federal Plaza Shopping Center, just 3.7km away, offering a vibrant atmosphere. Soons Orchards, located 4.3km away, provides a charming market feel. If you're up for a drive, Harriman Plaza Shopping Center, also 4.3km away, awaits with more family-friendly options.

Recreation

Experience the vibrant atmosphere at The Rock Sports Complex, where you can engage in various sports activities. Indulge in luxury at The Golf Club at Mansion Ridge, offering exquisite surroundings for a round of golf. For more sports excitement, visit Michie Stadium, known for its energetic vibe.

Adventure

Experience the thrill of motor racing at Orange County Fair Speedway, located 5.6km from Chester, where the adrenaline rush meets a vibrant atmosphere. Alternatively, enjoy skiing at Mount Peter Ski Area, 5.0km away, or explore the scenic Continental Road Trailhead, also 5.0km from Chester, for outdoor adventures.

Nightlife

For a lively night in Chester, visit Castle Fun Center for family-friendly arcade fun. Just 6.2km away, the Paramount Theatre offers a charming blend of culture and romance. For thrill-seekers, the Alpine Mountain Coaster, located 10.6km away, promises an exhilarating ride under the stars.

Booking tips and Expedia advantages for Chester

Chester, New York, offers numerous ways to save during your visit. Enjoy free entry to attractions like Sterling Forest State Park and explore the town without spending a penny. For budget-friendly accommodation, consider visiting between January and March, with Tuesday being the cheapest day to stay. Use Expedia to compare prices and find eco-certified hotels, and take advantage of package deals that combine flights and activities for better savings. Remember to filter prices from lowest to highest for the best rates available.

  • 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 selections based on your budget, preferred location, and desired hotel type. For instance, selecting the Eco-certified option will showcase sustainable and environmentally friendly hotels that are currently available. To discover the best prices and offers, 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 near Chester

Chester, New York, is an ideal destination for families and those seeking entertainment or urban experiences. Visitors can explore stunning national and state parks, picturesque lakes, and urban parks, all offering a mix of outdoor adventures, scenic beauty, and cultural experiences. With a variety of attractions to discover, Chester promises an enjoyable getaway for all travellers looking to immerse themselves in nature and local charm.

  • Bear Mountain State Park: Located 9.3km from Chester, this national park offers a stunning blend of adventure and outdoor activities. You can hike scenic trails, enjoy breathtaking views of the Hudson River, and experience the natural beauty that makes this park a haven for nature enthusiasts.
  • Storm King Art Center: Just 7.5km away, this renowned arts centre features expansive outdoor installations set against a picturesque landscape. The combination of large-scale sculptures and rolling hills provides a unique cultural experience that celebrates both art and nature.
  • Harriman State Park: Situated 8.1km from Chester, this state park is steeped in history and offers a variety of recreational opportunities. Explore its rich heritage through hiking, picnicking, and discovering the remnants of old estates amidst the lush woodlands.

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 a visit to Chester, New York, you have several major airports to consider. John F. Kennedy International Airport (JFK) is situated 34.8km away, with nearby hotels such as the luxurious Arlo Williamsburg and The William Vale, both 6.8km from the airport. Newark Liberty International Airport (EWR) is 29.2km from Chester, offering upscale options like The Dominick and 33 Hotel, both located 5.6km away. LaGuardia Airport (LGA) is the closest at 28.6km, featuring top-rated accommodations like Virgin Hotels New York City and Hilton Club The Quin, both 3.7km from the airport, ensuring convenient access to your travel needs.

Frequently asked questions

What is the best area to stay in Chester?
The best area to stay in Chester is the village centre, particularly around Main Street and the surrounding blocks.

This area is the heart of Chester, offering a pleasant and convenient experience for visitors. Main Street is lined with local shops, eateries, and historic buildings, creating a welcoming feel. You'll find attractions like the Chester Historical Society Museum and the Sugar Loaf Performing Arts Center nearby. The village is also known for its strong community spirit and regular events.

Couples looking for a relaxing getaway will appreciate the village centre. It offers a selection of cosy bed and breakfasts and boutique hotels, providing a more personal touch. You can enjoy strolls through the village, browse antique shops, and dine at local restaurants without needing to drive. The nearby Black Dirt Region is also easily accessible for wine tasting or farm visits, making for enjoyable day trips.

For families, staying within the village centre provides easy access to the local parks and ice cream parlours. The village green often hosts community gatherings and is a pleasant spot for children to play.
What are the best hotels in Chester that travellers recommend?
For hotels in Chester that travellers recommend, the Holiday Inn Express Hotel & Suites Chester by IHG is a superb choice.

This hotel, with an 8.6 rating, offers comfortable and clean rooms with premium bedding, ensuring a restful stay. Guests frequently praise the friendly and great staff, as well as the delicious and good complimentary breakfast, including convenient to-go options. The indoor pool is known for being clean, and there are pool sun loungers available for relaxation. The hotel is also located within a shopping district and is just 0.6 km from Castle Fun Centre and 3.2 km from LEGOLAND® New York.
What are the best family hotels in Chester?
For families visiting Chester, the Holiday Inn Express Hotel & Suites Chester by IHG and The Dominion House Bed & Breakfast are both excellent choices.

The Holiday Inn Express Hotel & Suites Chester by IHG, with a rating of 8.6, is a highly recommended option for families. Guests frequently mention the friendly staff and delicious complimentary breakfast. The hotel offers comfortable and clean rooms, some with sofa beds and connecting room options, which are ideal for families. A clean pool is also available for guests to enjoy. It is conveniently located just 0.6 km from the Castle Fun Centre and 3.2 km from LEGOLAND® New York. Free self-parking and free WiFi are also provided.

Another superb choice is The Dominion House Bed & Breakfast, which boasts an outstanding rating of 9.6. This accommodation provides amenities such as cribs and a shared children's playground, suiting families. Guests can also benefit from free breakfast, free self-parking, and free wired internet in public areas.
What hotels in Chester offer free breakfast?
Two excellent hotels in Chester offering complimentary breakfast are The Dominion House Bed & Breakfast and the Holiday Inn Express Hotel & Suites Chester by IHG.

The Dominion House Bed & Breakfast, with an impressive 9.6 rating, provides a delightful free breakfast to start your day. Guests also benefit from complimentary wired internet in public areas, free RV, bus, and truck parking, and free toiletries.

Another great option is the Holiday Inn Express Hotel & Suites Chester by IHG, a 3-star hotel with an 8.6 rating. This hotel offers a free breakfast, including a convenient to-go option, along with free self-parking and complimentary wired internet in public areas. Guests frequently praise the friendly staff, delicious breakfast, and comfortable, clean rooms.
What are the best budget hotels in Chester?
For budget hotels in Chester, consider the Holiday Inn Express Hotel & Suites Chester by IHG or The Dominion House Bed & Breakfast.

The Holiday Inn Express Hotel & Suites Chester by IHG, with an 8.6 rating, offers comfortable and clean rooms, and guests frequently highlight the friendly and great staff. The hotel provides free Wi-Fi, free wired internet in public areas, and complimentary toiletries. A delicious and good breakfast is included, and a to-go breakfast option is also available. Free self-parking is another convenient feature.

Another excellent option is The Dominion House Bed & Breakfast, which boasts an impressive 9.6 rating. This charming bed and breakfast provides free wired internet in public areas, free toiletries, and complimentary breakfast. Guests will also appreciate the free self-parking and the availability of free RV, bus, and truck parking.
What are the best hotels in Chester near LEGOLAND® New York?
For a highly-rated hotel in Chester near LEGOLAND® New York, the Holiday Inn Express Hotel & Suites Chester by IHG is an excellent option.

This hotel, with an 8.6 rating, is conveniently located just 3.2 kilometres from LEGOLAND® New York. Guests frequently praise the friendly and great staff, delicious and good breakfast, and comfortable and clean rooms. It has features friendly for families such as connecting rooms and sofa beds, as well as complimentary breakfast with a to-go option, free self-parking, and free Wi-Fi. The clean pool is also a popular feature.
When is the best time to go to Chester?
The best time to visit Chester, New York, is generally during the late spring (May to June) and early autumn (September to October) when the weather is pleasant for outdoor activities and exploring the region.

Late spring offers comfortable temperatures, typically ranging from 15°C to 25°C, making it ideal for walking, visiting local farms, and enjoying the natural beauty of the Hudson Valley. The foliage is lush and green, and many local attractions, such as farmers' markets and outdoor events, begin to open for the season. This period is particularly good for solo travellers or couples looking for a relaxed getaway with opportunities for scenic drives and light outdoor recreation without the peak summer crowds.

Early autumn provides a spectacular display of fall colours, especially from late September through October, with temperatures usually between 10°C and 20°C. This is a prime time for couples or solo travellers who appreciate picturesque landscapes and outdoor activities like apple picking at local orchards or exploring nearby state parks. The crisp air and vibrant scenery make it a popular time for wine tasting tours at local vineyards.

While summer (July to August) is also a popular time with warmer weather for lakes and outdoor adventures, it can be busier and hotter.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chester.
How can I save on a Chester hotel booking with Expedia?
Members always get our best prices. Find our best Chester hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Chester hotel?
Prices for hotels in Chester often vary, but you can find a great deal from £49 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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