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Chester Hotels

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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 P6,895
P8,489 total
includes taxes & fees
Nov 15 - Nov 16
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, (241 reviews)
"Amazing! The historic home sits on 40 acres of beautiful land inviting all guests to sit back and unwind. The beautiful home is decorated exquisitely and the hosts are warm and welcoming. If you are visiting West Point this place is a short drive away. It is nestled in a beautiful area making it an excellent option for a weekend get away-whether you are going to watch an Army football game or just want to get away, you will not be disappointed."
United States
Sally
The price is P13,600
P15,385 total
includes taxes & fees
Nov 16 - Nov 17
The Dominion House Bed & Breakfast

3. Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,128 reviews)
"Great stay, thanks"
United States
Gina
The price is P7,262
P8,215 total
includes taxes & fees
Nov 24 - Nov 25
Sleep Inn & Suites Monroe - Woodbury

4. 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)
"Clean rooms, nice staff, and convenience to Lego Land"
United States
Aeron
The price is P8,160
P10,047 total
includes taxes & fees
Nov 15 - Nov 16
Fairfield Inn & Suites by Marriott Goshen Middletown

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 P5,638
P14,944 total
includes taxes & fees
Nov 20 - Nov 21
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, (1,152 reviews)
"The room and bathroom were clean"
United States
Scott
The price is P6,990
P8,606 total
includes taxes & fees
Dec 1 - Dec 2
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, (1,001 reviews)
"Nice, laid back hotel with great staff."
United States
William
The price is P7,151
P8,447 total
includes taxes & fees
Dec 6 - Dec 7
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, (1,000 reviews)
"Great stay, great play area for the family in the lobby"
United States
Jarrod
The price is P5,228
P6,176 total
includes taxes & fees
Nov 29 - Nov 30
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, (796 reviews)
"My favorite to be staying in there"
United States
Md
The price is P6,072
P7,173 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express & Suites Middletown - Goshen by IHG

10. Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
3.0 star property
Middletown
9.0 out of 10, Wonderful, (799 reviews)
"The room with two beds are very spacious and clean. I have stayed here 4 times this year!"
United States
Nyowa
The price is P9,624
P11,590 total
includes taxes & fees
Nov 19 - Nov 20
Home2 Suites by Hilton Middletown

11. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very good, (1,011 reviews)
"We love taking our daughter here to swim, pool is nice & the rooms are always clean!"
United States
Jailene
The price is P6,442
P7,609 total
includes taxes & fees
Dec 13 - Dec 14
Courtyard by Marriott Middletown Goshen

12. Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (353 reviews)
"Great quick stay!"
United States
Lady
The price is P12,588
P14,869 total
includes taxes & fees
Nov 29 - Nov 30
Residence Inn by Marriott Middletown Goshen

13. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,256 reviews)
"Great stay"
Canada
Justine
The price is P6,455
P7,624 total
includes taxes & fees
Dec 10 - Dec 11
Sleep Inn & Suites Middletown - Goshen

14. 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 P9,140
P10,797 total
includes taxes & fees
Dec 11 - Dec 12
Homewood Suites Stewart Airport

15. Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport
2.5 star property
Newburgh
9.2 out of 10, Wonderful, (1,001 reviews)
"Clean good breakfast friendly staff"
United States
CAREN
The price is P8,549
P10,098 total
includes taxes & fees
Nov 22 - Nov 23
Hampton Inn & Suites Newburgh Stewart Airport

16. Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.4 out of 10, Very good, (1,000 reviews)
"Room was clean, bed was comfortable."
United States
Amanda
The price is P5,592
P6,605 total
includes taxes & fees
Dec 10 - Dec 11
Hampton Inn by Hilton Middletown

17. 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 P15,308
P18,848 total
includes taxes & fees
Nov 16 - Nov 17
The Orange Inn Boutique Hotel

18. Microtel Inn & Suites by Wyndham Middletown

Microtel Inn & Suites by Wyndham Middletown
2.0 star property
Middletown
6.8 out of 10, (1,000 reviews)
"Very loud and quite run down"
United States
Christine
The price is P5,861
P6,923 total
includes taxes & fees
Nov 15 - Nov 16
Microtel Inn & Suites by Wyndham Middletown

19. Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG
2.5 star property
Montgomery
8.8 out of 10, Excellent, (941 reviews)
"Good stay"
United States
Mike
The price is P7,133
P8,425 total
includes taxes & fees
Dec 13 - Dec 14
Holiday Inn Express & Suites Montgomery by IHG

20. Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very good, (217 reviews)
"Our stay was great !"
United States
Vu andyvu
The price is P7,088
P8,726 total
includes taxes & fees
Nov 22 - Nov 23
Comfort Suites Central Valley - Woodbury
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.

Hotels recommended for families in Chester

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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 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.