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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
8.6 out of 10, Excellent, (1,001 reviews)
"great stay"
United States
Annette
The price is ᅣ20,703
ᅣ25,492 total
includes taxes & fees
Jul 2 - Jul 3
Holiday Inn Express Hotel & Suites Chester by IHG

2. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 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 ᅣ34,774
ᅣ39,338 total
includes taxes & fees
Jun 30 - Jul 1
The Dominion House Bed & Breakfast

3. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,042 reviews)
"Another great stay!"
United States
Kimberly
The price is ᅣ20,282
ᅣ23,958 total
includes taxes & fees
Jul 26 - Jul 27
Sleep Inn & Suites Middletown - Goshen

4. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very Good, (1,000 reviews)
"I spoiled myself and had a room with a little balcony that overlooked very well landscaped garden/outdoor seating areas. This was definitely an escape from home restful stay!"
United States
Diane
The price is ᅣ17,735
ᅣ20,949 total
includes taxes & fees
Jul 26 - Jul 27
Courtyard by Marriott Middletown Goshen

5. 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, (1,003 reviews)
"We stopped here for the night and it was perfect. Clean room and courteous staff."
United States
Kathleen
The price is ᅣ15,865
ᅣ18,741 total
includes taxes & fees
Jul 12 - Jul 13
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

6. Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (630 reviews)
"Very clean and staff helpful "
United States
Kaiden
The price is ᅣ17,759
ᅣ20,067 total
includes taxes & fees
Jun 29 - Jun 30
Days Inn by Wyndham Wurtsboro

7. The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh
3.0 star property
Newburgh
7.2 out of 10, Good, (795 reviews)
"Very clean room parking was safe and easy and the staff was helpful"
United States
Michael
The Crossroads Hotel, Newburgh

8. Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,005 reviews)
"Nice Clean Hotel"
United States
James
The price is ᅣ18,244
ᅣ21,550 total
includes taxes & fees
Jul 6 - Jul 7
Hampton Inn by Hilton Middletown

9. Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very Good, (62 reviews)
"Family trip with 3 kids and we love it"
Canada
Pheng Theam
The price is ᅣ17,840
ᅣ21,968 total
includes taxes & fees
Jul 26 - Jul 27
Comfort Suites Central Valley - Woodbury

10. Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,002 reviews)
"staff was very friendly, hotel was very clean, breakfast was nice"
United States
Victoria
The price is ᅣ19,003
ᅣ22,447 total
includes taxes & fees
Jul 12 - Jul 13
Tru by Hilton Middletown

11. The Hamlet Inn at Warwick

The Hamlet Inn at Warwick
2.5 star property
Warwick
7.6 out of 10, Good, (168 reviews)
"The location was very convenient"
United States
Stephen
The price is ᅣ13,829
ᅣ15,645 total
includes taxes & fees
Jun 29 - Jun 30
The Hamlet Inn at Warwick

12. High Point Motel

High Point Motel
2.0 star property
Sussex
9.2 out of 10, Wonderful, (156 reviews)
"Great place if looking for pet friendly quiet stat"
United States
John H
The price is ᅣ14,233
ᅣ15,888 total
includes taxes & fees
Jun 30 - Jul 1
High Point Motel

13. Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,101 reviews)
"The room was pristine, breakfast great, ample and easy parking, very warm staff!"
United States
Akunna
The price is ᅣ19,553
ᅣ22,119 total
includes taxes & fees
Jul 26 - Jul 27
Sleep Inn & Suites Monroe - Woodbury

14. 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, (1,005 reviews)
"Our room was clean and comfortable. It was just what we wanted for a short overnight stay. The staff were very friendly and accommodating. I would definitely stay there again."
United States
ANNE
The price is ᅣ16,365
ᅣ18,922 total
includes taxes & fees
Jul 26 - Jul 27
Quality Inn & Suites Fishkill South near I-84

15. Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook
2.5 star property
Montgomery
6.4 out of 10, (1,002 reviews)
"Simple and easy quiet stay for overnight"
United States
Jose
The price is ᅣ12,292
ᅣ13,906 total
includes taxes & fees
Jun 29 - Jun 30
Super 8 by Wyndham Montgomery Maybrook

16. Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah
2.5 star property
Mahwah
8.8 out of 10, Excellent, (1,499 reviews)
"Great hotel and in an area where you have access to necessities like food or drinks and gas!"
United States
Carl
The price is ᅣ22,307
ᅣ25,570 total
includes taxes & fees
Jul 12 - Jul 13
Hampton Inn & Suites Mahwah

17. Best Western The Inn at Ramsey-Mahwah

Best Western The Inn at Ramsey-Mahwah
3.0 star property
Ramsey
7.2 out of 10, Good, (1,003 reviews)
"Had a pleasant stay very clean and alot of options for the breakfast."
United States
IMRAN
The price is ᅣ16,496
ᅣ18,909 total
includes taxes & fees
Jul 6 - Jul 7
Best Western The Inn at Ramsey-Mahwah

18. Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point
2.0 star property
Newburgh
4.8 out of 10, (1,011 reviews)
"It’s close to Dennys, this place needs serious update and cleaning."
United States
Albert
The price is ᅣ11,645
ᅣ13,757 total
includes taxes & fees
Jun 30 - Jul 1
Ramada by Wyndham Newburgh/West Point

19. 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)
"Great staff and breakfast"
United States
Giovanni
The price is ᅣ19,797
ᅣ23,386 total
includes taxes & fees
Jul 26 - Jul 27
La Quinta Inn & Suites by Wyndham Middletown-Goshen

20. Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG
2.5 star property
Montgomery
8.6 out of 10, Excellent, (877 reviews)
"Our stay for a day was great."
United States
Chime
The price is ᅣ18,924
ᅣ21,408 total
includes taxes & fees
Jul 12 - Jul 13
Holiday Inn Express & Suites Montgomery 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 a variety of attractions perfect for families, ensuring everyone has fun.
  • Beautiful Outdoor Scenery: Explore local national and state parks, lakes, and urban parks for stunning views and outdoor adventures.
  • Unique Shopping Experiences: Discover charming shops in the city center that reflect the vibrant local charm.
  • Engaging Entertainment: Enjoy recreational activities at the leisure center and a delightful cinema for a fun night out.
  • Diverse Accommodations: Choose from a range of hotels, including pet-friendly and agritourism options, catering to all travel needs.

Find great hotels near Chester

Discover a variety of hotel accommodations in Chester, New York, perfect for every type of traveler. Whether you're seeking a pet-friendly stay, a family vacation experience, or business travel amenities, Chester offers options to suit your needs. Explore agritourism properties and traditional hotels that provide comfort and convenience, along with favorable reviews to help you make the best choice for your getaway.

  • Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point: This budget-friendly hotel offers a welcoming atmosphere for families and business travelers alike, located 21km from Chester. With a guest rating of 8.4 out of 10, it excels in providing essential amenities and services tailored to those traveling with children and pets. Guests can enjoy complimentary cribs for infants and a pet-friendly policy that accommodates dogs and cats. The hotel's convenient location near Stewart Airport and West Point makes it an ideal choice for visitors to the Hudson Valley area.
  • Super 8 by Wyndham Middletown: Situated 14km from Chester, Super 8 by Wyndham Middletown is a budget-friendly motel that combines comfort with convenience. Guests can unwind with a variety of entertainment options, including premium TV channels and satellite TV. The nearby shopping outlets provide an opportunity for leisure activities and exploration. This motel is designed for travelers looking for straightforward accommodations with essential amenities, making it a practical choice for a relaxed stay.
  • Howard Johnson by Wyndham Newburgh/West Point: Located 23km from Chester, Howard Johnson by Wyndham Newburgh/West Point caters to business travelers seeking affordable lodging with essential conveniences. This budget-friendly hotel provides a comfortable environment for those visiting the area for work or leisure. Its strategic location allows easy access to local attractions and business hubs, making it a solid choice for individuals and groups needing a reliable base during their stay in the Hudson Valley region.

Where to stay near Chester

Chester, New York, offers a delightful blend of family-friendly activities and vibrant local charm. Explore the city center for unique shopping experiences and enjoy the warm atmosphere created by friendly locals. Venture into the picturesque Cheshire countryside for scenic views and outdoor fun, ensuring a memorable vacation. Whether you seek relaxation or adventure, Chester provides the perfect backdrop for a friendly getaway filled with diverse experiences.

  • Middletown: Situated about 16km from Chester, Middletown is a vibrant city known for its family-friendly attractions and entertainment options. Visitors often flock here for a city-themed experience, making it a great spot for shopping and leisure. The city features a bustling shopping mall, resorts, and a variety of dining establishments. Popular local landmarks include a theme park and a lively tourist precinct, providing ample opportunities for fun and relaxation. With visitor numbers peaking in spring and summer, Middletown offers a lively atmosphere that caters to families and entertainment seekers alike.
  • Goshen: Just 6km from Chester, Goshen is a charming city that attracts visitors year-round. Known for its family-oriented and entertainment-themed experiences, Goshen is home to shopping centers and resorts that appeal to all ages. The city’s landmarks, including a popular theme park and a vibrant tourist square, make it a delightful destination for a day trip or an extended visit. Peak travel times occur in March, July, and September, ensuring a lively environment filled with activities for everyone.
  • Monroe: Located 8km away from Chester, Monroe offers a unique blend of family-friendly and business-themed experiences. This city is perfect for travelers looking to enjoy shopping centers and ski resorts during the winter months. Monroe is also surrounded by stunning natural landmarks, including a picturesque lake and mountain views, ideal for outdoor enthusiasts. With peak visitor times in the summer and early fall, Monroe provides a charming atmosphere for both leisure and business travelers alike.

Things to do near Chester

Shopping

In Chester, you can explore local shops for unique gifts and souvenirs. If you're up for a drive, visit the Woodbury Common Premium Outlets, located about 16km away, featuring a variety of popular brand-name stores at discounted prices.

Recreation

Discover the tranquility of the Hudson Valley at the Monticello Wellness Center, where you can indulge in yoga classes and rejuvenating spa treatments. For outdoor enthusiasts, the nearby hiking trails offer scenic views and a chance to connect with nature, promoting relaxation and well-being.

Adventure

Experience the thrill of motor racing at the Orange County Fair Speedway, located 14km from Chester, where you can immerse yourself in the excitement of high-speed events. For a rush of adrenaline, head to Zoom Ziplines, 27km away, and soar through the treetops in an outdoor adventure.

Nightlife

In Chester, the nightlife offers a cozy atmosphere with local bars and live music venues. Enjoy craft cocktails at the Village Tavern or catch a show at the Chester Theatre. The laid-back vibe invites you to unwind and connect with friendly locals after a day of exploring.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Chester

Chester, New York, offers a variety of attractions perfect for family and city-themed vacations. Visitors can explore the beautiful scenery at local national and state parks, lakes, and urban parks. Notable points of interest include the Chester Zoo, Chester Racecourse, and the historic Chester Cathedral. For accommodations, Liverpool hotels are available nearby, making it easy for travelers to enjoy both outdoor adventures and cultural experiences in this charming area.

  • Bear Mountain State Park: Located 24km from Chester, Bear Mountain State Park offers stunning views and outdoor adventures. Hike the scenic trails, enjoy picnicking by the lake, or explore the park’s rich wildlife. It’s an ideal spot for nature lovers seeking both tranquility and adventure.
  • Harriman State Park: Just 21km away, Harriman State Park is steeped in history, featuring remnants of old structures and beautiful landscapes. Wander through the park’s extensive trail system that showcases its historical significance while enjoying the serene environment.
  • Algonquin Park: Situated 26km from Chester, Algonquin Park is a vibrant urban park perfect for families. Enjoy outdoor activities, playgrounds, and picnic areas amidst the city vibes, providing a refreshing escape for both relaxation and recreation.

Best time to go to Chester

The best time to visit Chester is dependent 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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 several major airports nearby. John F. Kennedy International Airport (JFK) is located 90km away, with luxurious hotel options like The William Vale and Arlo Williamsburg, both 18km from the airport. Newark Liberty International Airport (EWR) is 76km away, offering top-rated hotels such as The Dominick and Four Seasons Hotel New York Downtown, both just 14km from EWR. LaGuardia Airport (LGA) is 74km from Chester, featuring upscale accommodations like The Plaza, A Fairmont Hotel, and Hilton Club The Quin New York, both within 10km of the airport. Each airport provides accessible transport options to these hotels.

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?
Lakefront Paradise Pool + Paddle Boats Sleeps 12: Visitors like this Chester vacation home rental. It offers an outdoor pool, a balcony, and air-conditioning to help you feel perfectly comfortable in your new surroundings. You can relax into your vacation 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 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. See all available hotels listed as LGBTQ-friendly in Chester.
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 LEGOLANDĀ® New York. In Chester, there are 22 hotels and other accommodations to choose from. Find out more about Chester.
What are the top places to visit in Chester?
Favorite places to visit include Castle Fun Center, The Rock Sports Complex, and Museum Village. Additionally, you'll find LEGOLANDĀ® New York 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.

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