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Our top choices for Chester hotels

1. Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.8 out of 10, Excellent, (1,002 reviews)
"Good place to stay."
United States
Stephanie
The price is SAR 364
SAR 448 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express Hotel & Suites Chester by IHG

2. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.6 out of 10, Exceptional, (240 reviews)
"The owners were so kind and attentive, and the grounds are absolutely beautiful! Delicious food, gorgeous mountain air, and the horses were adorable. Thank you for having us!"
United States
Sinead
The price is SAR 404
SAR 457 total
includes taxes & fees
11 Nov - 12 Nov
The Dominion House Bed & Breakfast

3. 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, (1,004 reviews)
"Clean rooms, nice staff, and convenience to Lego Land"
United States
Aeron
The price is SAR 484
SAR 596 total
includes taxes & fees
9 Nov - 10 Nov
Fairfield Inn & Suites by Marriott Goshen Middletown

4. Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,124 reviews)
"Great stay, thanks"
United States
Gina
The price is SAR 399
SAR 452 total
includes taxes & fees
29 Nov - 30 Nov
Sleep Inn & Suites Monroe - Woodbury

5. LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.2 out of 10, Very good, (139 reviews)
"Love this place and so does my kids. The food is not good so make sure you eat off the resort and out of the park"
United States
danielle
The price is SAR 478
SAR 1,056 total
includes taxes & fees
13 Nov - 14 Nov
LEGOLAND Hotel NEW York

6. Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,156 reviews)
"Close to restaurants and shopping, grocery store close as well."
United States
Timothy
The price is SAR 444
SAR 546 total
includes taxes & fees
15 Nov - 16 Nov
Hampton Inn Harriman Woodbury

7. 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, (1,003 reviews)
"Nice, laid back hotel with great staff."
United States
William
The price is SAR 424
SAR 501 total
includes taxes & fees
6 Dec - 7 Dec
La Quinta Inn & Suites by Wyndham Middletown-Goshen

8. Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,006 reviews)
"Great stay, great play area for the family in the lobby"
United States
Jarrod
The price is SAR 323
SAR 382 total
includes taxes & fees
22 Nov - 23 Nov
Tru by Hilton Middletown

9. Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG
2.5 star property
Middletown
8.8 out of 10, Excellent, (794 reviews)
"My favorite to be staying in there"
United States
Md
The price is SAR 334
SAR 395 total
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express & Suites Middletown - Goshen by IHG

10. Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (352 reviews)
"Great quick stay!"
United States
Lady
The price is SAR 672
SAR 794 total
includes taxes & fees
29 Nov - 30 Nov
Residence Inn by Marriott Middletown Goshen

11. The Orange Inn Boutique Hotel

The Orange Inn Boutique Hotel
2.0 star property
Goshen
9.8 out of 10, Exceptional, (184 reviews)
"Lovely hotel. Wonderful location, excellent restaurant"
United States
Judy
The price is SAR 863
SAR 1,063 total
includes taxes & fees
9 Nov - 10 Nov
The Orange Inn Boutique Hotel

12. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very good, (1,009 reviews)
"We love taking our daughter here to swim, pool is nice & the rooms are always clean!"
United States
Jailene
The price is SAR 396
SAR 467 total
includes taxes & fees
19 Nov - 20 Nov
Courtyard by Marriott Middletown Goshen

13. Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
3.0 star property
Middletown
9.0 out of 10, Wonderful, (797 reviews)
"My stay with my family here was fantastic."
United States
Carl
The price is SAR 571
SAR 688 total
includes taxes & fees
16 Nov - 17 Nov
Home2 Suites by Hilton Middletown

14. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,255 reviews)
"Great stay"
Canada
Justine
The price is SAR 394
SAR 466 total
includes taxes & fees
9 Nov - 10 Nov
Sleep Inn & Suites Middletown - Goshen

15. Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very good, (212 reviews)
"Our stay was great !"
United States
Vu andyvu
The price is SAR 419
SAR 516 total
includes taxes & fees
22 Nov - 23 Nov
Comfort Suites Central Valley - Woodbury

16. Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.4 out of 10, Very good, (1,002 reviews)
"Room was clean, bed was comfortable."
United States
Amanda
The price is SAR 341
SAR 403 total
includes taxes & fees
3 Dec - 4 Dec
Hampton Inn by Hilton Middletown

17. Homewood Suites Stewart Airport

Homewood Suites Stewart Airport
3.0 star property
New Windsor
9.2 out of 10, Wonderful, (1,000 reviews)
"Great breakfast selection, very clean property overall"
United States
Victoria
The price is SAR 593
SAR 701 total
includes taxes & fees
4 Dec - 5 Dec
Homewood Suites Stewart Airport

18. 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 SAR 1,261
SAR 1,552 total
includes taxes & fees
5 Dec - 6 Dec
Stagecoach Inn

19. Microtel Inn & Suites by Wyndham Middletown

Microtel Inn & Suites by Wyndham Middletown
2.0 star property
Middletown
6.8 out of 10, (1,001 reviews)
"Very loud and quite run down"
United States
Christine
The price is SAR 348
SAR 411 total
includes taxes & fees
15 Nov - 16 Nov
Microtel Inn & Suites by Wyndham Middletown

20. Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG
2.5 star property
Middletown
9.4 out of 10, Exceptional, (93 reviews)
"Great hotel to stay very clean and friendly"
United States
Antonio
The price is SAR 443
SAR 523 total
includes taxes & fees
7 Dec - 8 Dec
Candlewood Suites Middletown Goshen by IHG
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 Center for go-karts, mini-golf, and arcade games.

A bridge with a plaque reading "City of Chester Queens Park Bridge 1923".

Top Chester Hotel Reviews

More cheap stays in Chester

Find out more about Chester

Top reasons to visit Chester

  • Family-Friendly Activities: Chester offers numerous entertainment options, perfect for a fun-filled family vacation.
  • Scenic Natural Attractions: Explore national and state parks, scenic lakes, and urban parks for outdoor adventures.
  • Charming Accommodations: Enjoy a variety of lodgings, from family-friendly hotels to unique agritourism properties.
  • Low Crowds and Warm Atmosphere: Experience the friendly locals and serene environment, ideal for relaxation.
  • Shopping and Entertainment: Discover local resorts, shopping centers, and event calendars for a vibrant city experience.

Find great hotels near Chester

Discover the charming lodging options in Chester, New York, where a variety of accommodations await to enhance your stay. From family-friendly hotels to pet-friendly agritourism properties, you'll find the perfect spot for your vacation needs. Whether you're traveling for business or leisure, Chester offers a selection of hotels that prioritize comfort and convenience. Explore top-rated hotels and read reviews to ensure a memorable experience in this picturesque town.

  • Red Roof Inn & Suites Newburgh – Stewart Airport/West Point: Nestled 22.5km from Chester, the Red Roof Inn & Suites Newburgh is an inviting hotel that perfectly caters to pet lovers and families. With its commitment to being pet-friendly and LGBTQIA welcoming, this hotel proudly aligns with LGBTQI travel guides, making it an inclusive choice for all travelers. The property offers amenities tailored for children, including complimentary cribs, ensuring a family-friendly atmosphere. Guests can enjoy the convenience of pet accommodations, allowing dogs and cats to join in on the fun. Experience a warm and welcoming environment designed for relaxation and enjoyment.
  • Super 8 by Wyndham Middletown: Located just 14.5km from Chester, Super 8 by Wyndham Middletown presents an affordable and comfortable motel option for those seeking convenience. Guests can unwind with entertainment options like television, premium TV channels, and satellite TV, perfect for evening relaxation. The proximity to nearby outlets offers shopping enthusiasts an exciting outing, making it an ideal choice for travelers looking to explore the local area. This motel’s combination of affordability and leisure activities makes it a great pick for budget-conscious visitors.
  • Howard Johnson by Wyndham Newburgh/West Point: Situated 22.5km from Chester, the Howard Johnson by Wyndham Newburgh is tailored for business travelers seeking comfort and convenience. With a focus on providing essential amenities for work and leisure, this hotel ensures a productive stay. Its strategic location allows for easy access to local businesses and attractions, making it a practical choice for those in town for meetings or conferences. Guests can expect a reliable experience that balances comfort and functionality for a seamless travel experience.

Where to stay near Chester

Chester, New York, offers a delightful blend of charm and family-friendly vibes, making it an ideal vacation spot. Explore the scenic beauty and low crowds while enjoying the warm atmosphere filled with friendly locals. Nearby regions provide a range of experiences, from budget-friendly options to luxurious escapes. Discover the best spots for entertainment and relaxation, ensuring a memorable stay in this quaint city.

  • Middletown: Located 16.1km from Chester, Middletown is a vibrant city that draws visitors with its family-friendly atmosphere and entertainment options. The travel experience here is enriched by access to shopping malls and resorts, making it a great spot for both leisure and retail therapy. Notable attractions include a nearby theme park and scenic lakes, perfect for family outings and outdoor activities. With peak visitor numbers in April and from June to July, the city offers a lively atmosphere during these months, making it an exciting destination for travelers.
  • Goshen: Situated just 6.4km from Chester, Goshen is a charming city that welcomes visitors year-round. Known for its family-oriented and entertainment-themed experiences, it features a variety of shopping centers and resorts. The city's attractions include a popular theme park and a picturesque town square, ideal for leisurely strolls and community events. With peaks in visitor numbers during March, July, and September, Goshen provides a lively yet pleasant atmosphere, making it a delightful stop for tourists seeking both adventure and relaxation.
  • Monroe: Monroe is located 8.0km from Chester and is known for its family-friendly, business, and city-themed experiences. Visitors can enjoy a variety of shopping options, including malls and ski resorts, catering to diverse interests. The proximity to a theme park, lake, and mountains adds to Monroe's appeal, offering outdoor and recreational activities. With peak travel times in June to July and September, Monroe is a bustling city that balances business and leisure, making it a great choice for a well-rounded vacation.

Things to do in and around Chester

Chester offers a variety of family-friendly activities and entertainment options, perfect for a city-themed vacation. Visitors can enjoy local resorts, shopping centers, and malls. Essential experiences include exploring event calendars, typical sightseeing spots, festive activities, and hiking trails. Whether you're looking for relaxation or adventure, Chester has something for everyone.

Shopping

The Monroe Federal Plaza Shopping Center, 9.7km from Chester, offers a vibrant mix of businesses and entertainment. Soons Orchards, 11.3km away, is perfect for local goods. The Old Glory Mall Shopping Center, 12.9km from Chester, features family-friendly shopping options. If you're up for a drive, check out other malls nearby.

Recreation

At The Rock Sports Complex, immerse yourself in an energetic atmosphere perfect for sports enthusiasts. Experience luxury at The Golf Club at Mansion Ridge, where you can enjoy pristine golf courses. For relaxation, visit Thomas Bull Memorial Park, offering serene trails and a peaceful retreat in nature.

Adventure

Experience the thrill of motor racing at Orange County Fair Speedway, located 14.5km from Chester, where adrenaline and excitement abound. Alternatively, hit the slopes at Mount Peter Ski Area, 12.9km away, for skiing adventures amidst stunning snowy landscapes. Enjoy the great outdoors at Continental Road Trailhead, also 12.9km from Chester.

Nightlife

In Chester, the Castle Fun Center offers an exciting arcadeAdventureZone filled with adventure vibes for a fun night out. For a more romantic evening, the Paramount Theatre and Ritz Theater, both nearby, provide captivating performances that blend entertainment and culture.

*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 several ways to save during your visit. Enjoy free access to attractions like Sterling Forest State Park and take advantage of public transport or car rentals for budget-friendly travel. For the best rates, plan your trip between January and March, as prices are lower during these months, with Tuesday being the least expensive day to stay. Use Expedia's search tool to find great hotel deals and consider bundling your hotel, flights, and activities for extra savings.

  • 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: Utilize Expedia's search tool to tailor your options based on your budget, desired location, and preferred hotel type. To discover the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel reservations in Chester with your flights and activities through an Expedia package deal.

Find the best attractions in and around Chester

Chester, New York, is perfect for family vacations and offers a blend of entertainment and city-themed experiences. Visitors can explore a variety of attractions, including national and state parks, scenic lakes, and urban parks. The area's points of interest cater to outdoor enthusiasts and culture seekers alike, providing a chance to enjoy the beautiful scenery and engage with the local environment.

  • Bear Mountain State Park: Experience the great outdoors at Bear Mountain State Park, just 24.1km from Chester. This stunning park offers breathtaking scenery, hiking trails, and opportunities for adventure like rock climbing and boating, making it perfect for nature enthusiasts.
  • United States Military Academy: Located 22.5km from Chester, the United States Military Academy is a prestigious institution with rich history. Explore its beautiful campus, learn about military traditions, and enjoy guided tours that provide insight into the training of future leaders.
  • Museum Village: Situated in Chester, Museum Village is a charming historic village that immerses visitors in local culture. With its authentic buildings and engaging exhibits, you can step back in time and discover the region's heritage.

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.

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

Traveling to Chester, New York, is convenient with access to three major airports. John F. Kennedy International Airport (JFK) is 90.1km away, with nearby hotels like Arlo Williamsburg, The William Vale, and The Boro Hotel, all rated 5 stars. Newark Liberty International Airport (EWR) is located 75.6km from Chester, featuring luxury options like The Dominick and Pendry Manhattan West, both 5 stars. Lastly, LaGuardia Airport (LGA) is 74.0km away, with top-rated hotels such as Virgin Hotels New York City and The Plaza - A Fairmont Managed Hotel. All airports offer various transportation services for easy access to these accommodations.

Frequently asked questions

What's the best place to stay in Chester?
Based on our traveler 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 options for your trip to the area are Overlook Lodge at Bear Mountain and Sleep Inn & Suites Middletown - Goshen. See all available top hotels, or vacation rentals in Chester.
What's the top vacation rental in Chester?
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: Visitors like this Chester vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill 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 most hotel bookings are refundable if you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, you might be able to still cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
Where can I learn more about changing or cancelling my trip to Chester?
For more details about updating your trip to Chester or cancelling it, click here.
What's the best place to stay for families 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. Kids of all ages will also enjoy a visit to Castle Fun Center. Find more child-friendly accommodations in Chester.
What is the favorite LGBTQ-friendly place to stay in Chester?
Holiday Inn Express Hotel & Suites Chester by IHG is a top LGBTQ-friendly hotel that features free breakfast and free WiFi. The Dominion House Bed & Breakfast is another good option for your trip.
Where is the best hotel to stay with easy access to The Rock Sports Complex?
Holiday Inn Express Hotel & Suites Chester, an IHG Hotel is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and an indoor pool. It's located just a short 0.8 mi (1.3 km) from The Rock Sports Complex. Other good options within 5 miles include Fairfield Inn & Suites by Marriott Goshen Middletown and NATURE'S NIRVANA FOR FAMILY AND FRIEND.
What about the best place to stay near Castle Fun Center?
One of the top choices for your stay is Holiday Inn Express Hotel & Suites Chester, an IHG Hotel, located a short 0.4 mi (0.6 km) from Castle Fun Center, and this hotel offers free breakfast and an indoor pool. Fairfield Inn & Suites by Marriott Goshen Middletown and Stagecoach Inn are two other good options within a few miles.
What are some accommodations 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 hotel near Stewart International Airport (SWF)?
Howard Johnson by Wyndham Newburgh is a popular hotel, featuring free breakfast and free WiFi. It's located a short 0.8 mi (1.2 km) from Stewart Intl. Airport. Other options within close proximity to the airport include Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport and Super 8 by Wyndham Newburgh/West Point Near Stewart Airport.
What is staying in Chester like?
Visitors to Chester are sure to enjoy the shopping and restaurants. Tourists can also enjoy the city's ski areas and coffeehouses. A top sight in the area is Woodbury Common Premium Outlets. In Chester, there are 21 hotels and other accommodations to choose from. Find out more about Chester.
What are the top places to visit in Chester?
Cultural venues include Museum Village and Sugar Loaf Performing Arts Center. Additionally, you'll find Woodbury Common Premium Outlets in the area. Check out what more 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 temp of 70°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Chester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.