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Chester Hotels

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Our top choices for Chester hotels

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, (1,008 reviews)
"great stay"
United States
Annette
The price is P7,280
P8,963 total
includes taxes & fees
Jul 2 - Jul 3
Holiday Inn Express Hotel & Suites Chester by IHG

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 P13,153
P14,879 total
includes taxes & fees
Jul 2 - Jul 3
The Dominion House Bed & Breakfast

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)
"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 P6,708
P7,924 total
includes taxes & fees
Jul 5 - Jul 6
Courtyard by Marriott Middletown Goshen

High Point Motel

High Point Motel
2.0 star property
Sussex
9.2 out of 10, Wonderful, (157 reviews)
"Great place if looking for pet friendly quiet stat"
United States
John H
The price is P5,628
P6,282 total
includes taxes & fees
Jul 2 - Jul 3
High Point Motel

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,046 reviews)
"Another great stay!"
United States
Kimberly
The price is P7,497
P8,856 total
includes taxes & fees
Jul 28 - Jul 29
Sleep Inn & Suites Middletown - Goshen

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, (879 reviews)
"Our stay for a day was great."
United States
Chime
The price is P6,423
P7,266 total
includes taxes & fees
Jul 5 - Jul 6
Holiday Inn Express & Suites Montgomery by IHG

Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook
2.5 star property
Montgomery
6.4 out of 10, (1,004 reviews)
"Simple and easy quiet stay for overnight"
United States
Jose
The price is P4,845
P5,481 total
includes taxes & fees
Jul 1 - Jul 2
Super 8 by Wyndham Montgomery Maybrook

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 P7,047
P7,964 total
includes taxes & fees
Jul 19 - Jul 20
Days Inn by Wyndham Wurtsboro

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, (1,004 reviews)
"We stopped here for the night and it was perfect. Clean room and courteous staff."
United States
Kathleen
The price is P6,001
P7,088 total
includes taxes & fees
Jul 19 - Jul 20
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Appalachian Motel

Appalachian Motel
2.0 star property
Vernon
7.6 out of 10, Good, (541 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 P4,129
P4,734 total
includes taxes & fees
Jul 7 - Jul 8
Appalachian Motel

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very Good, (63 reviews)
"Family trip with 3 kids and we love it"
Canada
Pheng Theam
The price is P6,398
P7,877 total
includes taxes & fees
Jul 20 - Jul 21
Comfort Suites Central Valley - Woodbury

Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah
2.5 star property
Mahwah
8.8 out of 10, Excellent, (1,503 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 P8,432
P9,665 total
includes taxes & fees
Jul 26 - Jul 27
Hampton Inn & Suites Mahwah

Rolling Hills Motel

Rolling Hills Motel
2.0 star property
Sussex
8.6 out of 10, Excellent, (217 reviews)
"Great staff and clean."
United States
John
The price is P5,628
P6,282 total
includes taxes & fees
Jul 15 - Jul 16
Rolling Hills Motel

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,120 reviews)
"I enjoyed my stay. The place was absolutely clean. Free breakfast was amazing and I will be going again"
United States
Khaleem
The price is P7,977
P9,822 total
includes taxes & fees
Jul 26 - Jul 27
Hampton Inn Harriman Woodbury

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,104 reviews)
"The room was pristine, breakfast great, ample and easy parking, very warm staff!"
United States
Akunna
The price is P7,392
P8,363 total
includes taxes & fees
Jul 26 - Jul 27
Sleep Inn & Suites Monroe - Woodbury

The Hamlet Inn at Warwick

The Hamlet Inn at Warwick
2.5 star property
Warwick
7.6 out of 10, Good, (169 reviews)
"The location was very convenient"
United States
Stephen
The price is P5,230
P5,917 total
includes taxes & fees
Jul 2 - Jul 3
The Hamlet Inn at Warwick

Holiday Inn Express Haskell - Wayne Area by IHG

Holiday Inn Express Haskell - Wayne Area by IHG
2.5 star property
Wanaque
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean and confortable, we will go back"
United States
damari
The price is P8,809
P10,098 total
includes taxes & fees
Jul 30 - Jul 31
Holiday Inn Express Haskell - Wayne Area by IHG

Days Inn by Wyndham Middletown

Days Inn by Wyndham Middletown
2.0 star property
New Hampton
6.4 out of 10, (694 reviews)
"Location was close to wedding venue I wouldn't stay here otherwise."
United States
Arthur
The price is P6,188
P7,309 total
includes taxes & fees
Jul 5 - Jul 6
Days Inn by Wyndham Middletown

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (1,004 reviews)
"Perfect for my weekend at the spartan race."
United States
Anthony
The price is P6,250
P7,164 total
includes taxes & fees
Jul 26 - Jul 27
Quality Inn near Mountain Creek

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, (1,006 reviews)
"Had a pleasant stay very clean and alot of options for the breakfast."
United States
IMRAN
The price is P6,239
P7,152 total
includes taxes & fees
Jul 7 - Jul 8
Best Western The Inn at Ramsey-Mahwah
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 delightful mix of attractions suitable for all ages, ensuring a memorable holiday for families.
  • Stunning Natural Parks: Explore beautiful national and state parks, serene lakes, and urban parks, perfect for outdoor enthusiasts.
  • Charming City Centre: The inviting Chester city centre features friendly locals and various shopping opportunities for every budget.
  • Accommodations for All: A range of hotels, including family-friendly and pet-friendly options, cater to diverse traveller needs.
  • Rich Cultural Experiences: Discover historic sites such as Chester Cathedral and enjoy local entertainment, enhancing your visit.

Find great hotels near Chester

Chester, New York offers a delightful selection of accommodations to suit all types of travellers. Whether you prefer a family-friendly hotel, a pet-friendly stay, or an agritourism property, you’ll find options that cater to your specific needs. With an emphasis on business travel and leisure experiences, Chester's hotels provide comfort and convenience, making it an ideal destination for your next vacation.

  • Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point: A welcoming choice for families and business travellers alike, Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point offers a budget-friendly lodging experience just 21km from Chester. With a commendable guest rating of 8.4 out of 10, this hotel features pet-friendly amenities, allowing dogs and cats with certain restrictions. Families travelling with young children will appreciate the availability of complimentary cribs. The property is committed to providing a comfortable stay while being conveniently located for access to local attractions and activities.
  • Super 8 by Wyndham Middletown: Located a mere 14km from Chester, Super 8 by Wyndham Middletown is an economical motel that caters to guests seeking simplicity and convenience. The hotel boasts entertainment options, including premium TV channels and satellite television, ensuring guests can unwind after a day of exploration. With nearby outlet shopping options, this establishment is ideal for those looking to enjoy a bit of retail therapy, while its straightforward amenities make it a suitable choice for budget-conscious travellers.
  • Howard Johnson by Wyndham Newburgh/West Point: Situated 23km from Chester, Howard Johnson by Wyndham Newburgh/West Point is a practical option for business travellers. This budget-friendly hotel offers essential amenities tailored for those visiting for work purposes. Guests can expect a comfortable atmosphere that prioritises convenience and accessibility to local business districts, making it a reliable choice for individuals looking to balance work and leisure during their stay in the Newburgh area.

Where to stay near Chester

Chester, New York, offers a delightful blend of family-friendly activities and vibrant city life. Explore the charming Chester city centre, where friendly locals enhance your experience. Venture into the picturesque Cheshire countryside for a relaxing escape, and indulge in various shopping opportunities that cater to all budgets. Whether you're seeking luxury or a budget-friendly getaway, Chester provides an inviting atmosphere for every traveller to enjoy.

  • Middletown: Situated 16km from Chester, Middletown offers a vibrant city atmosphere perfect for families and entertainment seekers. The travel experience here is dynamic, with visitor numbers peaking during the spring and summer months, particularly in April and from June to July. Popular venues include shopping centres and resort facilities that cater to all ages. Notable local attractions include a theme park and a bustling tourist precinct, making it an ideal spot for those looking to enjoy a mix of leisure and fun.
  • Goshen: Located a mere 6km from Chester, Goshen is a charming city known for its family-friendly environment and entertainment options. Visitors can expect a pleasant travel experience year-round, with peaks in March, July, and September. The city features shopping centres and resorts that provide a variety of attractions, including a delightful square and a theme park. Goshen is perfect for those seeking a blend of city life and recreational activities, ensuring a memorable stay for all.
  • Monroe: Just 8km from Chester, Monroe is a bustling city that combines family fun with business opportunities. The travel experience here is consistent throughout the year, with peak visitor numbers from June to July and September. Monroe boasts shopping centres and ski facilities, catering to a diverse range of interests. Nature enthusiasts will appreciate the proximity of local landmarks such as a picturesque lake and scenic mountains, making Monroe an excellent choice for those looking to explore both urban and natural attractions.

Things to do near Chester

Shopping

In Chester, you can explore local shops and boutiques for unique gifts and souvenirs. If you're up for a drive, visit the Woodbury Common Premium Outlets, about 19km away, where you'll find a variety of branded goods at discounted prices.

Recreation

Explore the serene atmosphere at The Spa at Glenmere Manor, where you can indulge in rejuvenating treatments and unwind in the tranquil gardens. For outdoor enthusiasts, the nearby Harriman State Park offers scenic hiking trails and opportunities for meditation amidst nature's beauty.

Adventure

For an adrenaline rush, visit Orange County Fair Speedway, located 14km from Chester, where you can experience the thrill of motor racing. Alternatively, Zoom Ziplines, 27km away, offers an exhilarating zipline ropes course, perfect for outdoor enthusiasts seeking adventure in the treetops.

For motor racing aficionados, Monticello Motor Club is a premier destination located 45km from Chester, providing an exciting environment for those eager to push the limits of speed and performance.

Nightlife

Chester's nightlife offers a quaint charm with local pubs like the iconic Chester Tavern for a laid-back pint, while The Chester Theatre Company often hosts engaging performances for a unique evening. For a lively atmosphere, explore music events at nearby venues that showcase local talent.

*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 various ways to save money during your visit. Enjoy free entry to attractions like Sterling Forest State Park, and consider travelling during the cheaper months of January to March, with Tuesdays being the most affordable days for accommodation. Use Expedia to compare hotel rates and find eco-friendly options. Bundling your hotel stay with flights and activities can also yield significant savings. For transportation, utilise public transport where possible to keep costs down while exploring this charming town.

  • 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, desired location, and other preferences. You can organise your results to display prices in ascending order, allowing you to view the most affordable hotels first. Additionally, you have the option to refine your search by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that you can book.
  • 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 offers a delightful mix of family-friendly activities and vibrant entertainment, ideal for city-themed getaways. Visitors can explore stunning national and state parks, serene lakes, and urban parks. Noteworthy attractions include the Chester Zoo, Chester Racecourse, and the historic Chester Cathedral. For comfortable stays, consider hotels in Liverpool, which is conveniently nearby. This region caters to those seeking outdoor adventures, cultural experiences, and scenic beauty.

  • Charles J. Everett Memorial: Situated 6km from Chester, this monument pays homage to local history and culture. Its serene setting makes it an ideal spot for reflection and appreciation of the community's heritage.
  • Ochs Orchard: Located 16km from Chester, this charming farm offers a delightful escape into nature. Visitors can enjoy picking seasonal fruits, indulging in freshly made treats, and experiencing the rustic beauty of the countryside.
  • Museum Village: Nestled within Chester, this historic village showcases the rich cultural tapestry of the area. With living history exhibits and period buildings, it provides an immersive glimpse into the past.

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

For a visit to Chester, New York, you can choose from several major airports. John F. Kennedy International Airport (JFK) is situated 90km away, with nearby hotels like The William Vale and Arlo Williamsburg, both 18km from the airport. Newark Liberty International Airport (EWR) is 76km away, offering luxurious stays at The Dominick and Four Seasons Hotel New York Downtown, both just 14km from the airport. LaGuardia Airport (LGA), located 74km from Chester, features top-notch hotels such as Hilton Club The Quin New York and The Plaza, A Fairmont Hotel, both within 10km of the airport. Each airport provides convenient access to Chester.

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.
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.
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.
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 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.