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Top hotels and accommodation in Chester

Countryside Motel

2.0 star property
7.2 out of 10, Good, (243)
"My husband Randy stayed at the hotel for pleasure. The hotel was clean, staff were friendly. It was quiet during the evening hours and it was convenient to restaurants and shops. The price was very good compared to all the other hotels."
The price is AU$160
includes taxes & fees
3 Aug - 4 Aug
Countryside Motel

Sussex Motel

2.5 star property
8.8 out of 10, Excellent, (322)
"Enjoyed our stay."
The price is AU$148
includes taxes & fees
1 Sept - 2 Sept
Sussex Motel

Hampton Inn & Suites Mahwah

2.5 star property
8.8 out of 10, Excellent, (1267)
"Will stay here again."
The price is AU$207
includes taxes & fees
17 Aug - 18 Aug
Hampton Inn & Suites Mahwah

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 star property
8.4 out of 10, Very good, (1003)
"Very clean and breakfast was worthy."
The price is AU$217
includes taxes & fees
7 Aug - 8 Aug
Holiday Inn Express Hotel & Suites Chester by IHG

The Dominion House Bed & Breakfast

2.0 star property
9.2 out of 10, Wonderful, (226)
"Amazing hospitality,"
The price is AU$377
includes taxes & fees
6 Aug - 7 Aug
The Dominion House Bed & Breakfast

SpringHill Suites by Marriott Fishkill

3.0 star property
9.6 out of 10, Exceptional, (967)
"Location was key to our visit. "
The price is AU$267
includes taxes & fees
24 Aug - 25 Aug
SpringHill Suites by Marriott Fishkill

High Point Motel

2.0 star property
8.6 out of 10, Excellent, (55)
"Location was great, cimfortable beds, friendly staff"
The price is AU$149
includes taxes & fees
3 Aug - 4 Aug
High Point Motel

Sleep Inn & Suites Monroe - Woodbury

2.5 star property
9.4 out of 10, Exceptional, (1004)
"Staff was friendly, room was very nice and clean, beds were very comfortable "
The price is AU$197
includes taxes & fees
10 Aug - 11 Aug
Sleep Inn & Suites Monroe - Woodbury

Rolling Hills Motel

2.0 star property
8.4 out of 10, Very good, (162)
"Very nice rooms and staff very quiet place for family Staff was very inviting "
The price is AU$149
includes taxes & fees
17 Aug - 18 Aug
Rolling Hills Motel

TAPA HOTEL

2.5 star property
9.0 out of 10, Wonderful, (322)
"Renovated and up-to-date, and clean. Good basic accomodations located off Rt. 17 and near NYS Thruway and GSP. Friendly staff / management."
The price is AU$229
includes taxes & fees
3 Aug - 4 Aug
TAPA HOTEL

Quality Inn & Suites Fishkill South near I-84

2.5 star property
8.8 out of 10, Excellent, (1006)
"Nice staff, short driving distance to eateries, quiet environment, clean and nice room for a short stay."
The price is AU$180
includes taxes & fees
7 Aug - 8 Aug
Quality Inn & Suites Fishkill South near I-84

Super 8 by Wyndham Montgomery Maybrook

2.5 star property
6.4 out of 10, (1009)
"Very nice clean and quit location. Staff was very accommodating and friendly."
The price is AU$150
includes taxes & fees
4 Aug - 5 Aug
Super 8 by Wyndham Montgomery Maybrook

Hampton Inn Fishkill

2.5 star property
8.6 out of 10, Excellent, (1000)
"Two good restaurants on site"
The price is AU$237
includes taxes & fees
17 Aug - 18 Aug
Hampton Inn Fishkill

Hampton Inn Harriman Woodbury

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Great stay great staff great accommodations "
The price is AU$229
includes taxes & fees
7 Aug - 8 Aug
Hampton Inn Harriman Woodbury

HYATT house Fishkill/Poughkeepsie

3.0 star property
8.8 out of 10, Excellent, (1003)
"Great place "
The price is AU$209
includes taxes & fees
10 Aug - 11 Aug
HYATT house Fishkill/Poughkeepsie

Appalachian Motel

2.0 star property
7.6 out of 10, Good, (487)
"If you looking for quite and convenient place, its for you"
The price is AU$120
includes taxes & fees
3 Aug - 4 Aug
Appalachian Motel

Wingate by Wyndham Fishkill

3.0 star property
7.6 out of 10, Good, (458)
"Very friendly staff"
The price is AU$183
includes taxes & fees
3 Aug - 4 Aug
Wingate by Wyndham Fishkill

Best Western Fishkill Inn & Suites

3.5 star property
8.8 out of 10, Excellent, (882)
"It was easy to get to and the staff was very courteous "
The price is AU$220
includes taxes & fees
10 Aug - 11 Aug
Best Western Fishkill Inn & Suites

Cadet Motel

2.0 star property
6.4 out of 10, (288)
"Great stay always. The staff are wonderful people. My go to when vist twice a year. Thank you again. See ya soon "
The price is AU$139
includes taxes & fees
5 Aug - 6 Aug
Cadet Motel

Comfort Suites Fishkill near Interstate 84

2.5 star property
9.0 out of 10, Wonderful, (1002)
"A relaxing experience there with the staff and easy navigating "
The price is AU$208
includes taxes & fees
17 Aug - 18 Aug
Comfort Suites Fishkill near Interstate 84
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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Learn more about Chester

Escape to relaxing Chester! Enjoy its dining and skiing.

Top Chester Hotel Reviews

Find out more about Chester

Find out more about Chester

Top reasons to visit Chester

  • Family-Friendly Activities: Chester boasts a range of attractions that cater to families, ensuring a fun-filled getaway for all ages.
  • Outdoor Adventures: Explore national parks, picturesque lakes, and urban parks perfect for nature lovers and those seeking scenic beauty.
  • Charming Neighbourhoods: Wander through friendly local communities and enjoy unique shopping opportunities.
  • Accommodation Variety: From budget-friendly hotels to luxurious stays, Chester offers diverse lodging options for every traveller.
  • Local Zoo: A visit to the local zoo promises a delightful day out for families and animal lovers.

Find great hotels near Chester

Explore a variety of accommodation options in Chester, New York, ideal for your holiday getaway. From family-friendly hotels to pet-friendly stays and agritourism properties, Chester offers a range of choices to suit any traveller's needs. Whether you're seeking a business-themed hotel or a cozy retreat, you'll find the perfect Chester hotel for a memorable experience.

  • Super 8 by Wyndham Middletown: Located a mere 14.5km from Chester, Super 8 by Wyndham Middletown offers a no-frills motel experience perfect for budget-conscious travellers. Enjoy complimentary dining options including a free breakfast on weekdays and weekends, along with wrapped food for on-the-go meals. The property features entertainment amenities such as satellite TV and premium channels, ensuring you stay connected during your visit. With nearby outlet shopping, this motel caters to those looking for convenience and affordability while exploring the area.
  • Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point: Situated 22.5km from Chester, this hotel is ideal for those seeking a welcoming atmosphere, especially for LGBTQIA travellers. With a pet-friendly policy and business-themed services, including a business centre and meeting rooms, it caters to both leisure and corporate guests. The property provides a unique blend of comfort and professionalism, allowing you to bring your furry companions along for the adventure. Enjoy a stay that respects diversity while delivering top-notch amenities.
  • Howard Johnson by Wyndham Newburgh/West Point: Also located 22.5km from Chester, Howard Johnson by Wyndham Newburgh/West Point focuses on providing a business-centric experience. Ideal for business travellers, this hotel offers dedicated services and facilities tailored to meet your corporate needs. With a commitment to comfort and convenience, guests can enjoy a pleasant stay equipped with essential amenities, making it an excellent choice for those visiting the area for work while being close to local attractions.

Where to stay near Chester

Chester, New York, offers a delightful blend of family-friendly fun and vibrant city experiences. Explore charming neighborhoods with friendly locals, indulge in unique shopping opportunities, and savour the serene beauty of the Cheshire countryside. Whether you're after budget-friendly options or a touch of luxury, Chester caters to all. Don't miss the chance to create unforgettable memories in this welcoming community, making it a perfect getaway for families and adventurers alike!

  • Middletown: Located a mere 16.1km from Chester, Middletown offers a vibrant city experience that caters to families and entertainment seekers alike. The city's attractions peak during the delightful months of April and from June to July, making it a popular summer destination. Visitors can enjoy a range of activities, from exploring the local theme park to shopping at the bustling malls and centres. With its tourist precinct and picturesque lake, Middletown is perfect for a day of family fun or a leisurely stroll.
  • Goshen: Just 6.4km from Chester, Goshen is a charming city known for its family-friendly atmosphere and lively entertainment options. With visitor numbers spiking in March, July, and September, it's a great spot for those looking to enjoy city life with a touch of nature. The local shopping centres and resorts provide plenty of options for relaxation and recreation. Don't miss exploring the historic square and nearby attractions, including the popular theme park, which offers excitement for all ages.
  • Monroe: Monroe is located 8.0km from Chester and is known for its mix of family-friendly activities, business opportunities, and city charm. The peak travel seasons are June to July and September, drawing visitors to its shopping malls and centres. Outdoor enthusiasts can explore nearby mountains and lakes, making it ideal for both relaxation and adventure. With a thriving theme park nearby, Monroe is perfect for families looking to blend leisure with a bit of thrill.

Things to do in and around Chester

Chester offers a fantastic blend of family-friendly activities and entertainment options, making it ideal for a city-themed getaway. You can enjoy some sightseeing, explore local shopping centres and malls, or tee off at nearby golf courses. With its appealing resorts, Chester ensures a fun-filled vacation for everyone.

Shopping

The nearest shopping spot is Monroe Federal Plaza Shopping Center, just 9.7km away, offering a lively blend of entertainment and family vibes. Soons Orchards, a charming public market 11.3km from Chester, features local produce and gifts. Harriman Plaza Shopping Center, also 11.3km away, has a variety of retail options.

Recreation

Experience the energetic atmosphere at Michie Stadium, perfect for sports enthusiasts. Indulge in luxury at The Golf Club at Mansion Ridge, where you can enjoy exquisite golfing. For a peaceful retreat, Thomas Bull Memorial Park offers serene walking trails and tranquil spots for relaxation amidst nature.

Adventure

Mount Peter Ski Area, located 12.9km from Chester, offers thrilling skiing experiences amid stunning snowy landscapes. For adrenaline-pumping action, visit Orange County Fair Speedway, 14.5km away, where you can witness exciting motor racing. Alternatively, explore the Continental Road Trailhead, 12.9km away, for scenic outdoor adventures.

Nightlife

In Chester, Castle Fun Center is perfect for family fun with its arcade and adventure activities. For a touch of culture, head to Paramount Theatre, 16.1km away, or Eisenhower Hall Theater, 25.7km away, both offering a mix of entertainment and romance in a charming setting.

*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 budget-friendly options for tourists, including free entry to attractions like Sterling Forest State Park. To save on accommodation, consider visiting between January and March when prices drop, and aim for a Tuesday stay, the cheapest day of the week. Utilize Expedia to find great deals on hotels and package options that combine flights and activities, ensuring you sort results by price from lowest to highest for the best bargains. Opt for public transport or car rentals to explore the area without overspending.

  • 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: Utilise Expedia’s search tool to refine your choices based on your budget, preferred location, and the type of accommodation you’re after. To find the best bargains and lowest prices, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save a bit of cash by combining your Chester hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Chester

Chester, New York, is perfect for family and city-themed vacations, offering a blend of outdoor adventures and cultural experiences. Explore national parks, picturesque lakes, and urban parks that cater to nature lovers and those seeking scenic beauty. Don't miss visiting the local zoo for a fun day out. For a comfortable stay, consider the best hotels in Chester to enhance your trip.

  • United States Military Academy: Located 22.5km from Chester, this prestigious institution offers a glimpse into the training of future military leaders. Take a guided tour to explore its historic grounds and learn about its significant role in American history.
  • Bear Mountain State Park: Just 24.1km away, this stunning national park is perfect for outdoor enthusiasts. With hiking trails, breathtaking views, and diverse wildlife, it offers a fantastic escape into nature.
  • Orange County Fairgrounds: Only 14.5km from Chester, these fairgrounds host a variety of events, from fairs to concerts, providing a lively atmosphere for families. Enjoy rides, games, and local food stalls for a fun day out.

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 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

For a visit to Chester, New York, you have several airport options. John F. Kennedy International Airport (JFK) is situated 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 from Chester, offering luxurious stays at The Dominick and 33 Hotel, both 14.5km away. Lastly, LaGuardia Airport (LGA) is 74.0km from Chester, with excellent hotels such as Virgin Hotels New York City and the Hilton Club The Quin, both just 9.7km away. Each airport provides convenient access to Chester for your holiday.

Frequently asked questions

What's the best place to stay in Chester?

The Dominion House Bed & Breakfast is ranked highly by Expedia customers. This B&B offers free breakfast and an outdoor pool. Holiday Inn Express Hotel & Suites Chester by IHG is another top choice for your trip based on traveller reviews. See all available top hotels, or vacation rentals in Chester.

What are some of the best holiday rentals that Chester has to offer?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This holiday home rental outside of Chester is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. 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's the best place to stay on a budget in Chester?

Based on reviews, Holiday Inn Express Hotel & Suites Chester, an IHG Hotel is a popular 2.5-star hotel for our travellers looking for an economical choice, and features free breakfast and free WiFi. View all budget hotels in Chester.

What's the best accommodation for a romantic getaway to Chester?

The Dominion House Bed & Breakfast is a favourite 3.5-star B&B for couples, and features wedding services and free breakfast. See all romantic hotels 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's the best accommodation option for a ski holiday in Chester?

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel is a top hotel for hitting the ski slopes, and features free breakfast and free WiFiThis hotel is located 21 minutes by car from Mount Peter Ski Area. See all ski hotels 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 the best spa hotel in Chester?

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel is a highly recommended spa hotel with a pool. See all spa hotels 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. Top sights around the area include LEGOLAND® New York and Woodbury Common Premium Outlets. In Chester, there are 17 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 Museum Village. Additionally, you'll find LEGOLAND® New York and Woodbury Common Premium Outlets in the area. 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.