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Our top choices for Chester hotels

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark
4.0 star property
Monticello
8.2 out of 10, Very good, (2,230 reviews)
"My family's and I love this resort."
United States
Arcadio
The price is AU$342
includes taxes & fees
14 June - 15 June
The Kartrite Resort & Indoor Waterpark

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1,146 reviews)
"Convenient location, clean room, staff friendly and helpful."
United States
Thomas
The price is AU$214
includes taxes & fees
21 June - 22 June
DoubleTree by Hilton Hotel Nanuet

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,114 reviews)
"Breakfast was ok parking and staff where excellent "
United States
Victor
The price is AU$233
includes taxes & fees
11 June - 12 June
Hampton Inn Harriman Woodbury

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, (1,003 reviews)
"Nice place"
United States
Akashdeep
The price is AU$200
includes taxes & fees
15 June - 16 June
Holiday Inn Express Hotel & Suites Chester by IHG

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
3.0 star property
Goshen
9.0 out of 10, Wonderful, (1,001 reviews)
"100% recommend this hotel. The continental breakfast was delicious. The staff was amazing and the location was ideal."
United States
Megan
The price is AU$248
includes taxes & fees
10 June - 11 June
Fairfield Inn & Suites by Marriott Goshen Middletown

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,026 reviews)
"Great breakfast, clean rooms "
United States
KASEY
The price is AU$203
includes taxes & fees
17 June - 18 June
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,088 reviews)
"The room was pristine, breakfast great, ample and easy parking, very warm staff!"
United States
Akunna
The price is AU$178
includes taxes & fees
17 June - 18 June
Sleep Inn & Suites Monroe - Woodbury

Stagecoach Inn

Stagecoach Inn
3.5 star property
Goshen
9.6 out of 10, Exceptional, (79 reviews)
"We only stayed one night, but it was very comfortable and the staff was friendly. "
United States
Kathryn
The price is AU$506
includes taxes & fees
6 July - 7 July
Stagecoach Inn

West Gate Inn Nyack

West Gate Inn Nyack
3.0 star property
Nyack
7.4 out of 10, Good, (1,319 reviews)
"Breakfast was ok. Rooms were very neat and the staff were awesome."
United States
Edmund
The price is AU$157
includes taxes & fees
7 June - 8 June
West Gate Inn Nyack

LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.8 out of 10, Excellent, (46 reviews)
"Clean room, friendly staff, plentiful breakfast "
United States
Michelle
The price is AU$760
includes taxes & fees
5 July - 6 July
LEGOLAND Hotel NEW York

Villa Verde BB Greenwood Lake NY

Villa Verde BB Greenwood Lake NY
4.0 star property
Monroe
10.0 out of 10, Exceptional, (21 reviews)
"Very nice B&B, with a very gracious host who served us a wonderful breakfast."
United States
Peter
The price is AU$351
includes taxes & fees
28 June - 29 June
Villa Verde BB Greenwood Lake NY

The Orange Inn Boutique Hotel

The Orange Inn Boutique Hotel
2.0 star property
Goshen
9.8 out of 10, Exceptional, (162 reviews)
"Great place to stay."
United States
Michael
The price is AU$427
includes taxes & fees
8 June - 9 June
The Orange Inn Boutique Hotel

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (235 reviews)
"I had a perfect stay with my girlfriend for a long weekend. Eric and Susie were amazing hosts, serving delicious breakfast each day. The hot tub was luxurious and the area was beautiful. I’d 100% come back."
United States
Anna
The price is AU$341
includes taxes & fees
8 June - 9 June
The Dominion House Bed & Breakfast

Inn at Stony Creek

Inn at Stony Creek
3.0 star property
Warwick
9.2 out of 10, Wonderful, (458 reviews)
"An extremely lovely property. Staff were amazing and caring. The best so far and will be returning very soon."
United States
Jose
The price is AU$366
includes taxes & fees
8 June - 9 June
Inn at Stony Creek

Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (59 reviews)
"Very friendly staff. Room was spacious and clean. Will return again!"
United States
Pasquale
The price is AU$230
includes taxes & fees
8 June - 9 June
Candlewood Suites Middletown Goshen by IHG

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)
"Safe area not too far from restaurants and stores."
United States
Richard
The price is AU$171
includes taxes & fees
7 June - 8 June
Americas Best Value Inn at Central Valley-Woodbury

Resorts World Catskills Casino

Resorts World Catskills Casino
4.5 star property
Monticello
8.8 out of 10, Excellent, (1,133 reviews)
"Room was very clean, staff were friendly."
United States
Deirdra
The price is AU$290
includes taxes & fees
10 June - 11 June
Resorts World Catskills Casino

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (1,004 reviews)
"The hotel was clean, breakfast had quite a few choices, staff was friendly and helpful Very much would stay here again."
United States
Michele
The price is AU$207
includes taxes & fees
7 June - 8 June
La Quinta Inn & Suites by Wyndham Middletown-Goshen

Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection
5.0 star property
Gardiner
9.4 out of 10, Exceptional, (67 reviews)
"Amazing stay! Will be back"
United States
Alison
The price is AU$2,115
includes taxes & fees
21 June - 22 June
Wildflower Farms, Auberge Collection

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very good, (1,003 reviews)
"Breakfast is over at 10am, the pool is open in the evening very small but overall good for kids. Great stay and price."
United States
Stacey
The price is AU$189
includes taxes & fees
10 June - 11 June
Courtyard by Marriott Middletown Goshen
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 accommodation in 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.

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?
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 Spark by Hilton Fishkill and DoubleTree by Hilton Hotel 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 a coffee maker, 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's the best family accommodation in Chester?
The Dominion House Bed & Breakfast is a B&B with an outdoor pool and free parking, and it's a top choice on Expedia for families. Also, children of all ages will enjoy a visit to Castle Fun Center. Find more child-friendly accommodations 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. Top sights around the area include LEGOLAND® New York and Woodbury Common Premium Outlets. 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 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.

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