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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, (1,006 reviews)
"great stay"
United States
Annette
The price is NT$3,796
NT$4,674 total
includes taxes & fees
Jun 14 - Jun 15
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 NT$6,799
NT$7,692 total
includes taxes & fees
Jun 24 - Jun 25
The Dominion House Bed & Breakfast

3. Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very Good, (54 reviews)
"Clean nice new hotel"
United States
Amjad
The price is NT$3,481
NT$4,286 total
includes taxes & fees
Jun 14 - Jun 15
Comfort Suites Central Valley - Woodbury

4. Tin Brook Bed & Breakfast

Tin Brook Bed & Breakfast
3.0 star property
Walden
9.4 out of 10, Exceptional, (122 reviews)
"Very nice accommodations & staff."
United States
Laurie
The price is NT$4,348
NT$4,919 total
includes taxes & fees
Jun 22 - Jun 23
Tin Brook Bed & Breakfast

5. High Point Motel

High Point Motel
2.0 star property
Sussex
9.2 out of 10, Wonderful, (150 reviews)
"My mom and I stayed here and it was a great experience. We were very happy with the room and when we needed batteries late at night they were quick to provide them. Definitely would stay here again."
United States
Stephanie
The price is NT$2,909
NT$3,248 total
includes taxes & fees
Jun 16 - Jun 17
High Point Motel

6. 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, (1,013 reviews)
"Clean, comfortable, safe, nice breakfast"
United States
Brett
The price is NT$3,478
NT$4,022 total
includes taxes & fees
Jul 13 - Jul 14
Quality Inn & Suites Fishkill South near I-84

7. Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1,025 reviews)
"Gorgeous setting, beautiful and comfortable room and easy access."
United States
Gwen
The price is NT$5,346
NT$6,582 total
includes taxes & fees
Jun 14 - Jun 15
Overlook Lodge at Bear Mountain

8. The Hamlet Inn at Warwick

The Hamlet Inn at Warwick
2.5 star property
Warwick
7.6 out of 10, Good, (166 reviews)
"The location was very convenient"
United States
Stephen
The price is NT$2,704
NT$3,059 total
includes taxes & fees
Jun 14 - Jun 15
The Hamlet Inn at Warwick

9. Budget Motor Inn - Stony Point

Budget Motor Inn - Stony Point
1.5 star property
Stony Point
5.2 out of 10, (562 reviews)
"Excellent "
United States
Tariq
The price is NT$1,968
NT$2,192 total
includes taxes & fees
Jun 24 - Jun 25
Budget Motor Inn - Stony Point

10. Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,095 reviews)
"The room was pristine, breakfast great, ample and easy parking, very warm staff!"
United States
Akunna
The price is NT$3,756
NT$4,249 total
includes taxes & fees
Jun 16 - Jun 17
Sleep Inn & Suites Monroe - Woodbury

11. Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (624 reviews)
"Very clean and staff helpful "
United States
Kaiden
The price is NT$3,638
NT$4,111 total
includes taxes & fees
Jun 14 - Jun 15
Days Inn by Wyndham Wurtsboro

12. 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, (1,013 reviews)
"We stopped here for the night and it was perfect. Clean room and courteous staff."
United States
Kathleen
The price is NT$3,103
NT$3,665 total
includes taxes & fees
Jun 28 - Jun 29
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

13. Sussex Motel

Sussex Motel
2.5 star property
Sussex
8.8 out of 10, Excellent, (405 reviews)
"Very convenient stay on our roadtrip-- simple check in/check out, the room was very tidy, parking was out front, area was quiet and felt safe :)"
United States
Mitchell
The price is NT$2,688
NT$3,000 total
includes taxes & fees
Jun 17 - Jun 18
Sussex Motel

14. Appalachian Motel

Appalachian Motel
2.0 star property
Vernon
7.6 out of 10, Good, (536 reviews)
"The rooms are very basic, but we had everything we needed for our stay. A really nice surprise was how comfortable the beds were. The motel is close to hiking trails. The parking lot for hiking Stairway to Heaven was a 2 minute drive from the motel. If you stay here in the winter, it is only a 5 minute drive from Mountain Creek ski resort. We would stay here again."
United States
Lorrie
The price is NT$2,135
NT$2,447 total
includes taxes & fees
Jun 16 - Jun 17
Appalachian Motel

15. Rolling Hills Motel

Rolling Hills Motel
2.0 star property
Sussex
8.6 out of 10, Excellent, (214 reviews)
"Great staff and clean."
United States
John
The price is NT$2,688
NT$3,001 total
includes taxes & fees
Jun 24 - Jun 25
Rolling Hills Motel

16. Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (1,001 reviews)
"Perfect for my weekend at the spartan race."
United States
Anthony
The price is NT$3,145
NT$3,604 total
includes taxes & fees
Jul 2 - Jul 3
Quality Inn near Mountain Creek

17. Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
8.2 out of 10, Very Good, (127 reviews)
"Easy check in, comfortable bed, minimal breakfast but enough to get us going."
United States
William
The price is NT$3,172
NT$3,668 total
includes taxes & fees
Jul 2 - Jul 3
Spark by Hilton Fishkill

18. Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,014 reviews)
"Nice Clean Hotel"
United States
James
The price is NT$3,568
NT$4,215 total
includes taxes & fees
Jun 17 - Jun 18
Hampton Inn by Hilton Middletown

19. Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook
2.5 star property
Montgomery
6.4 out of 10, (1,003 reviews)
"Simple and easy quiet stay for overnight"
United States
Jose
The price is NT$2,758
NT$3,120 total
includes taxes & fees
Jun 24 - Jun 25
Super 8 by Wyndham Montgomery Maybrook

20. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,032 reviews)
"Very comfortable stay! One night only, just passing through. Very nice breakfast layout and assortment. Would stay again!"
United States
David
The price is NT$3,877
NT$4,579 total
includes taxes & fees
Jun 16 - Jun 17
Sleep Inn & Suites 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 Center for go-karts, mini-golf, and arcade games.

The Queens Park Bridge, a landmark of Chester

Top Chester Hotel Reviews

More cheap stays in Chester

Hotels in Chester with star-rating

Find out more about Chester

Top reasons to visit Chester

  • Outdoor Adventures: Chester boasts stunning national and state parks, perfect for hiking and exploring nature's beauty.
  • Family-Friendly Activities: The town offers a variety of attractions and entertainment options suitable for all ages.
  • Charming Neighborhoods: Experience the warm hospitality of Chester's friendly locals in its quaint neighborhoods.
  • Variety of Accommodations: Choose from family-friendly, pet-friendly, and luxury stays to suit any traveler's needs.
  • Scenic Lakes and Parks: Relax by picturesque lakes or enjoy leisure activities in urban parks.

Find great hotels near Chester

Discover a variety of hotel accommodations in Chester, New York, perfect for every traveler. Whether you're seeking family-friendly options, pet-friendly stays, or business-oriented services, Chester offers a range of choices to suit your needs. Enjoy the charm of agritourism properties and the comfort of well-reviewed hotels, ensuring a delightful vacation experience in this picturesque town.

  • Super 8 by Wyndham Middletown: This motel offers a convenient and budget-friendly lodging option located 14.5km from Chester. Super 8 by Wyndham Middletown is designed for travelers seeking comfort without breaking the bank. Guests can enjoy a variety of entertainment options with premium TV channels and satellite TV in their rooms. The nearby outlets provide a great opportunity for shopping enthusiasts, ensuring a delightful stay filled with leisure and fun.
  • Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point: Situated 22.5km away from Chester, this hotel caters to a diverse range of travelers, including those traveling with pets and LGBTQIA individuals. Red Roof Inn & Suites is recognized for its warm, welcoming atmosphere and commitment to inclusivity, making it a standout choice for business or leisure visitors. The hotel features a pet-friendly policy, allowing dogs and cats, along with various amenities to ensure a comfortable stay for both you and your furry companions.
  • Howard Johnson by Wyndham Newburgh/West Point: Also located 22.5km from Chester, Howard Johnson is tailored for business travelers seeking modern conveniences during their stay. This hotel combines practicality with comfort, offering amenities designed to support work and relaxation. With its strategic location, guests can easily access nearby attractions while enjoying a professional environment that meets their needs.

Where to stay near Chester

Chester, New York, offers a delightful mix of family-friendly activities and charming local spots. Visitors can enjoy low crowds while exploring the city's vibrant atmosphere, perfect for entertainment and leisure. From quaint neighborhoods to convenient accommodations, Chester provides a warm welcome with friendly locals. Nearby attractions also enhance the experience, ensuring there's something for every traveler. Whether you're seeking budget-friendly options or a touch of luxury, Chester is a charming destination worth exploring.

  • Middletown: Located a short drive from Chester, Middletown is a vibrant city known for its family-friendly atmosphere and entertainment options. The city offers a variety of attractions, including a popular resort and bustling shopping malls. Visitors can enjoy outdoor activities at local lakes or thrill-seeking adventures at nearby theme parks. With a peak in visitors during the warmer months, Middletown has something for everyone, making it a fantastic stop for those seeking a lively city experience.
  • Goshen: Just a few miles from Chester, Goshen is a charming city that draws travelers with its blend of family fun and urban experiences. Known for its inviting shopping centers and resorts, Goshen also features modern squares that become lively hubs for social gatherings. The city sees a surge of visitors in the spring and summer months, inviting you to explore its local attractions, including an exciting theme park and a vibrant tourist precinct, perfect for families and city explorers alike.
  • Monroe: Monroe, positioned conveniently close to Chester, is a delightful city that offers a mix of family-oriented activities and business opportunities. Visitors flock to Monroe for its shopping centers and ski resorts, which provide both winter sports and retail therapy. The city is surrounded by beautiful landscapes, including lakes and mountains, making it ideal for outdoor enthusiasts. With peak travel times in late spring and early fall, Monroe is an excellent destination for those seeking a well-rounded experience.

Things to do in and around Chester

Chester, New York, offers a delightful mix of family-friendly activities and entertainment options. Enjoy a stay at a local resort, explore shopping centers and malls, and check out event calendars for festive activities. Don’t miss out on typical sightseeing opportunities and ensure you’re equipped with hiking essentials to explore the scenic surroundings. Chester is perfect for creating memorable vacation experiences.

Shopping

In Chester, you can visit Monroe Federal Plaza Shopping Center, just 9.7km away, for a family-friendly experience. Soons Orchards, 11.3km away, offers a charming public market vibe. Old Glory Mall, located 12.9km away, combines entertainment and shopping for a fun day out.

Recreation

The Rock Sports Complex in Chester offers an energetic atmosphere with various sports activities to engage in. For a touch of luxury, visit The Golf Club at Mansion Ridge, where you can enjoy a round of golf amidst picturesque views. Thomas Bull Memorial Park provides a serene environment perfect for relaxation and wellness.

Adventure

Experience the thrill of racing at the Orange County Fair Speedway, located 14.5km from Chester, where adrenaline meets excitement. For winter sports enthusiasts, Mount Peter Ski Area, 12.9km away, offers fantastic skiing opportunities. Alternatively, explore the scenic Continental Road Trailhead, 12.9km from Chester, perfect for outdoor adventures.

Nightlife

Experience the fun at Castle Fun Center, where family vibes and adventure await. For a more romantic evening, catch a show at the nearby Paramount Theatre or Ritz Theater, both offering captivating performances that blend culture and entertainment just a short drive from Chester.

*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 entry to attractions like Sterling Forest State Park, and consider traveling between January and March for lower accommodation rates. Tuesdays are the most affordable days to stay, while Saturdays tend to be pricier. Utilize Expedia’s search tool to find budget-friendly hotels by sorting prices and filtering for eco-friendly options. Additionally, save by bundling your hotel, flights, and activities. Be on the lookout for last-minute deals and compare room rates for the best 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: Expedia's search tool enables you to specify your budget, choose your desired location, and much more. You can easily arrange your search results to display prices from the lowest to the highest, ensuring you find the most affordable hotels first. Additionally, you can refine your selections by hotel type; for instance, checking the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that are available for booking.
  • 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 in and around Chester

Chester, New York, is perfect for family and entertainment-themed vacations, offering a variety of attractions like national and state parks, lakes, and urban parks. Visitors can enjoy outdoor activities, cultural experiences, and beautiful scenery. Whether you're hiking through lush landscapes or relaxing by the water, Chester provides a delightful escape for travelers seeking both adventure and tranquility.

  • Bear Mountain State Park: Experience the breathtaking scenery and adventure opportunities at Bear Mountain State Park, located 24.1km from Chester. With hiking trails, picnicking areas, and stunning views of the Hudson River, it's a perfect spot for nature lovers and outdoor enthusiasts.
  • United States Military Academy: Situated 22.5km from Chester, the United States Military Academy at West Point offers a rich history and a chance to explore the prestigious institution that trains future leaders. Guided tours highlight its remarkable architecture and scenic grounds.
  • Museum Village: Right in Chester, Museum Village is a charming historic village that immerses you in local culture. Experience hands-on exhibits and demonstrations that showcase 19th-century life, making it a delightful visit for history buffs and families alike.

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

When visiting Chester, New York, you have several major airports to choose from. John F. Kennedy International Airport (JFK) is located 90.1km away and features nearby hotels like Arlo Williamsburg, The William Vale, and The Boro Hotel, all approximately 17.7km from the airport. Newark Liberty International Airport (EWR) is 75.6km from Chester, with luxury options such as The Dominick, The Beekman, and Pendry Manhattan West, situated about 9 to 16.1km from the airport. Lastly, LaGuardia Airport (LGA), located 74.0km away, offers accommodations like Virgin Hotels New York City and The Plaza, both within 5 to 9.7km of the airport.

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 Spark by Hilton Fishkill and DoubleTree by Hilton Hotel Nanuet. See all available top hotels, or 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. Top sights around the area include LEGOLAND® New York and Woodbury Common Premium Outlets. In Chester, there are 18 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 LEGOLAND® New York and 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.

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