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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, (1,000 reviews)
"Good place to stay."
United States
Stephanie
The price is NZ$212
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, (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 NZ$432
includes taxes & fees
12 Nov - 13 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, (1,000 reviews)
"Clean rooms, nice staff, and convenience to Lego Land"
United States
Aeron
The price is NZ$282
includes taxes & fees
12 Nov - 13 Nov
Fairfield Inn & Suites by Marriott Goshen Middletown

4. 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 NZ$419
includes taxes & fees
13 Nov - 14 Nov
LEGOLAND Hotel NEW York

5. Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,131 reviews)
"Great stay, thanks"
United States
Gina
The price is NZ$228
includes taxes & fees
22 Nov - 23 Nov
Sleep Inn & Suites Monroe - Woodbury

6. Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,158 reviews)
"Close to restaurants and shopping, grocery store close as well."
United States
Timothy
The price is NZ$243
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn Harriman Woodbury

7. 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 NZ$201
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express & Suites Middletown - Goshen by IHG

8. 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, (1,009 reviews)
"Nice, laid back hotel with great staff."
United States
William
The price is NZ$237
includes taxes & fees
6 Dec - 7 Dec
La Quinta Inn & Suites by Wyndham Middletown-Goshen

9. Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,008 reviews)
"Great stay, great play area for the family in the lobby"
United States
Jarrod
The price is NZ$178
includes taxes & fees
29 Nov - 30 Nov
Tru by Hilton Middletown

10. 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 NZ$244
includes taxes & fees
15 Nov - 16 Nov
Comfort Suites Central Valley - Woodbury

11. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very good, (1,010 reviews)
"We love taking our daughter here to swim, pool is nice & the rooms are always clean!"
United States
Jailene
The price is NZ$221
includes taxes & fees
23 Nov - 24 Nov
Courtyard by Marriott Middletown Goshen

12. 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 NZ$325
includes taxes & fees
19 Nov - 20 Nov
Home2 Suites by Hilton Middletown

13. 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 NZ$235
includes taxes & fees
22 Nov - 23 Nov
Candlewood Suites Middletown Goshen by IHG

14. Microtel Inn & Suites by Wyndham Middletown

Microtel Inn & Suites by Wyndham Middletown
2.0 star property
Middletown
6.8 out of 10, (1,004 reviews)
"Very loud and quite run down"
United States
Christine
The price is NZ$194
includes taxes & fees
29 Nov - 30 Nov
Microtel Inn & Suites by Wyndham Middletown

15. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,257 reviews)
"Great stay"
Canada
Justine
The price is NZ$225
includes taxes & fees
10 Dec - 11 Dec
Sleep Inn & Suites Middletown - Goshen

16. Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.4 out of 10, Very good, (1,003 reviews)
"Room was clean, bed was comfortable."
United States
Amanda
The price is NZ$184
includes taxes & fees
10 Dec - 11 Dec
Hampton Inn by Hilton Middletown

17. 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 NZ$237
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express & Suites Montgomery by IHG

18. 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 NZ$375
includes taxes & fees
29 Nov - 30 Nov
Residence Inn by Marriott Middletown Goshen

19. Parkway House Goshen Family-Friendly Bed & Breakfast

Parkway House Goshen Family-Friendly Bed & Breakfast
3.0 star property
Goshen
9.8 out of 10, Exceptional, (49 reviews)
"One of the best places we’ve stayed at, highly recommended!"
United States
Aakif
The price is NZ$252
includes taxes & fees
12 Nov - 13 Nov
Parkway House Goshen Family-Friendly Bed & Breakfast

20. Americas Best Value Inn at Central Valley-Woodbury

Americas Best Value Inn at Central Valley-Woodbury
2.0 star property
Central Valley
7.2 out of 10, Good, (1,006 reviews)
"Great place, clean quiet, helpful staff"
United States
Marlon
The price is NZ$216
includes taxes & fees
12 Nov - 13 Nov
Americas Best Value Inn at Central Valley-Woodbury
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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 Centre 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

Recent Reviews in Chester

More cheap accommodation in Chester

Find out more about Chester

Top reasons to visit Chester

  • Charming City Centre: Chester boasts a welcoming city centre filled with friendly locals, perfect for leisurely strolls and shopping.
  • Family-Friendly Activities: Enjoy a mix of entertainment options, including a delightful cinema and a leisure centre catering to all ages.
  • Stunning Outdoor Adventures: Explore the beautiful Cheshire countryside, national parks, and lakes for unforgettable outdoor experiences.
  • Diverse Accommodation: Choose from a range of lodging options, from agritourism to modern hotels, catering to various needs.
  • Rich Cultural Experiences: Visit local attractions like Chester Zoo and Chester Cathedral for a taste of the area's heritage.

Find great hotels near Chester

Discover a variety of accommodation options in Chester, New York, where you can enjoy a perfect blend of comfort and convenience. Whether you’re seeking a family-friendly getaway, a pet-friendly stay, or a space tailored for business travel, Chester's hotels cater to all types of visitors. With options ranging from charming agritourism properties to modern hotels, you're sure to find the ideal base for your adventure in this picturesque region.

  • Red Roof Inn & Suites Newburgh – Stewart Airport/West Point: Located 20.9km from Chester, Red Roof Inn & Suites Newburgh – Stewart Airport/West Point offers a budget-friendly accommodation that caters to families, business travellers, and those with pets. Guests appreciate the welcoming atmosphere and the convenience of free cribs for children. The hotel embraces a pet-friendly policy, accommodating your furry companions with various restrictions. With a guest rating of 8.4 out of 10, this property ensures a comfortable stay while providing essential amenities that cater to both business and leisure needs.
  • Super 8 by Wyndham Middletown: Just 14.5km from Chester, Super 8 by Wyndham Middletown is a budget motel that delivers a straightforward and comfortable lodging experience. Guests can unwind with entertainment options including television, satellite TV, and premium channels. The nearby outlet shopping adds a touch of excitement for those looking to explore the local scene. This property is an excellent choice for budget-conscious travellers seeking a convenient base from which to experience the surrounding area.
  • Howard Johnson by Wyndham Newburgh/West Point: Situated 22.5km from Chester, Howard Johnson by Wyndham Newburgh/West Point provides a budget-friendly option tailored for business travellers. With a focus on practicality and comfort, this hotel features essential amenities designed to meet the needs of those on work-related trips. The property offers a convenient location, making it easy for guests to access key business areas and attractions in the vicinity.

Where to stay near Chester

Chester, New York, offers a delightful blend of family-friendly experiences and vibrant city life. Explore the charming Chester city centre, where friendly locals create a welcoming atmosphere. Venture into the stunning Cheshire countryside for outdoor adventures, and indulge in a varied shopping experience that caters to all budgets. Whether you're seeking a relaxing getaway or a lively family vacation, Chester promises a memorable stay filled with warmth and hospitality.

  • Middletown: Situated a mere 16.1km from Chester, Middletown is a vibrant city perfect for family adventures and entertainment. With a diverse range of attractions, visitors can enjoy the lively shopping mall centre and various resorts. The city is particularly bustling during the peak months of April and June to July, making it an excellent time to explore local landmarks such as the theme park and tourist precinct. Whether you're looking for a fun day out or a shopping spree, Middletown offers a rich urban experience amidst its charming surroundings.
  • Goshen: Just 6.4km from Chester, Goshen is a delightful city that appeals to families and entertainment seekers alike. Known for its welcoming atmosphere, the city draws visitors throughout the year, with peak times in March, July, and September. Goshen features a variety of popular activities, including visits to its shopping mall centre and local resorts. The nearby theme park and tourist precinct offer exciting escapades for all ages, ensuring that your time in Goshen is filled with memorable experiences.
  • Monroe: Only 8.0km from Chester, Monroe is a charming city that balances family fun with business opportunities. The city experiences a steady stream of visitors, peaking in June to July and September. Monroe boasts a mix of shopping centres and ski venues, making it a great destination for both leisure and business travellers. Nature lovers will appreciate the proximity to stunning landmarks such as the lake and mountain, providing a perfect backdrop for outdoor activities. Monroe's unique offerings make it an ideal spot for exploring the great outdoors while enjoying city conveniences.

Things to do near Chester

Shopping

Chester offers a charming shopping experience with local boutiques and gift shops. For a wider selection, if you're up for a drive, head to nearby shopping malls like Woodbury Common Premium Outlets, about 24.1km away, where you can find an array of designer brands at discounted prices.

Recreation

In Chester, the Mohonk Mountain House offers a serene spa experience with treatments inspired by nature, surrounded by breathtaking mountain views. Nearby, the Hudson Valley offers hiking trails and peaceful lakes, perfect for leisurely strolls and reconnecting with nature's beauty.

Adventure

Experience thrilling motor racing at Orange County Fair Speedway, located 14.5km from Chester, where the adrenaline rush of the track awaits. For a different adventure, head to Zoom Ziplines, 27.4km away, and soar through the trees, enjoying the outdoor scenery. Palisades Climb Adventure, 40.2km from Chester, offers a fun-filled ropes course and zipline experience.

Nightlife

Explore the lively atmosphere at The Chester Tavern, where you can enjoy a variety of beers and local bands. For a more laid-back vibe, visit The Copper Door for tasty cocktails and a welcoming ambience. Both spots offer a taste of Chester's vibrant nightlife scene.

*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, is perfect for family and entertainment-themed getaways, offering a variety of attractions like national parks, lakes, and urban parks. Visitors can enjoy outdoor activities, cultural experiences, and stunning scenery. While exploring the area, consider staying at local hotels and visiting attractions such as Chester Zoo, Chester Racecourse, and Chester Cathedral for a memorable experience.

  • Bear Mountain State Park: Located 24.1km from Chester, this expansive park offers stunning landscapes and a variety of outdoor activities. Enjoy scenic hikes, wildlife spotting, and breathtaking views from the summit, making it ideal for adventure seekers and nature lovers alike.
  • Algonquin Park: Just 25.7km away, this urban park blends city life with natural beauty. Families can enjoy spacious picnic areas, walking paths, and playgrounds, providing a perfect escape from the hustle and bustle of urban living.
  • Arrow Park Lake and Lodge: Situated 11.3km from Chester, this picturesque lake features a charming beach and scenic surroundings. It's a romantic spot for couples looking to relax, swim, or enjoy a peaceful day by the water.

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.

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

Flying into Chester, New York, is convenient with three major airports nearby. John F. Kennedy International Airport (JFK) is 90.1km away, with excellent hotels like The William Vale and Arlo Williamsburg, both 17.7km from the airport. Newark Liberty International Airport (EWR) is 75.6km away, offering luxury options such as The Dominick and Four Seasons Hotel New York Downtown, situated 14.5km from the airport. LaGuardia Airport (LGA) is 74.0km from Chester, featuring top-rated hotels like Hilton Club The Quin New York and The Plaza, both approximately 5 to 9.7km from the airport. Each airport provides accessible transportation to these accommodations, ensuring a pleasant arrival experience.

Frequently asked questions

What is the best area to stay in Chester?
The best area to stay in Chester is the village centre, particularly around Main Street and the surrounding blocks.

This area is the heart of Chester, offering a pleasant and convenient experience for visitors. Main Street is lined with local shops, eateries, and historic buildings, creating a welcoming feel. You'll find attractions like the Chester Historical Society Museum and the Sugar Loaf Performing Arts Center nearby. The village is also known for its strong community spirit and regular events.

Couples looking for a relaxing getaway will appreciate the village centre. It offers a selection of cosy bed and breakfasts and boutique hotels, providing a more personal touch. You can enjoy strolls through the village, browse antique shops, and dine at local restaurants without needing to drive. The nearby Black Dirt Region is also easily accessible for wine tasting or farm visits, making for enjoyable day trips.

For families, staying within the village centre provides easy access to the local parks and ice cream parlours. The village green often hosts community gatherings and is a pleasant spot for children to play.
What are the best hotels in Chester that travellers recommend?
For hotels in Chester that travellers recommend, the Holiday Inn Express Hotel & Suites Chester by IHG is a superb choice.

This hotel, with an 8.6 rating, offers comfortable and clean rooms with premium bedding, ensuring a restful stay. Guests frequently praise the friendly and great staff, as well as the delicious and good complimentary breakfast, including convenient to-go options. The indoor pool is known for being clean, and there are pool sun loungers available for relaxation. The hotel is also located within a shopping district and is just 0.6 km from Castle Fun Centre and 3.2 km from LEGOLAND® New York.
What are the best family hotels in Chester?
For families visiting Chester, the Holiday Inn Express Hotel & Suites Chester by IHG and The Dominion House Bed & Breakfast are both excellent choices.

The Holiday Inn Express Hotel & Suites Chester by IHG, with a rating of 8.6, is a highly recommended option for families. Guests frequently mention the friendly staff and delicious complimentary breakfast. The hotel offers comfortable and clean rooms, some with sofa beds and connecting room options, which are ideal for families. A clean pool is also available for guests to enjoy. It is conveniently located just 0.6 km from the Castle Fun Centre and 3.2 km from LEGOLAND® New York. Free self-parking and free WiFi are also provided.

Another superb choice is The Dominion House Bed & Breakfast, which boasts an outstanding rating of 9.6. This accommodation provides amenities such as cribs and a shared children's playground, suiting families. Guests can also benefit from free breakfast, free self-parking, and free wired internet in public areas.
What hotels in Chester offer free breakfast?
Two excellent hotels in Chester offering complimentary breakfast are The Dominion House Bed & Breakfast and the Holiday Inn Express Hotel & Suites Chester by IHG.

The Dominion House Bed & Breakfast, with an impressive 9.6 rating, provides a delightful free breakfast to start your day. Guests also benefit from complimentary wired internet in public areas, free RV, bus, and truck parking, and free toiletries.

Another great option is the Holiday Inn Express Hotel & Suites Chester by IHG, a hotel with an 8.6 rating. This hotel offers a free breakfast, including a convenient to-go option, along with free self-parking and complimentary wired internet in public areas. Guests frequently praise the friendly staff, delicious breakfast, and comfortable, clean rooms.
What are the best budget hotels in Chester?
For budget hotels in Chester, consider the Holiday Inn Express Hotel & Suites Chester by IHG or The Dominion House Bed & Breakfast.

The Holiday Inn Express Hotel & Suites Chester by IHG, with an 8.6 rating, offers comfortable and clean rooms, and guests frequently highlight the friendly and great staff. The hotel provides free Wi-Fi, free wired internet in public areas, and complimentary toiletries. A delicious and good breakfast is included, and a to-go breakfast option is also available. Free self-parking is another convenient feature.

Another excellent option is The Dominion House Bed & Breakfast, which boasts an impressive 9.6 rating. This charming bed and breakfast provides free wired internet in public areas, free toiletries, and complimentary breakfast. Guests will also appreciate the free self-parking and the availability of free RV, bus, and truck parking.
What are the best hotels in Chester near LEGOLAND® New York?
For a highly-rated hotel in Chester near LEGOLAND® New York, the Holiday Inn Express Hotel & Suites Chester by IHG is an excellent option.

This hotel, with an 8.6 rating, is conveniently located just 3.2 kilometres from LEGOLAND® New York. Guests frequently praise the friendly and great staff, delicious and good breakfast, and comfortable and clean rooms. It has features friendly for families such as connecting rooms and sofa beds, as well as complimentary breakfast with a to-go option, free self-parking, and free Wi-Fi. The clean pool is also a popular feature.
When is the best time to go to Chester?
The best time to visit Chester, New York, is generally during the late spring (May to June) and early autumn (September to October) when the weather is pleasant for outdoor activities and exploring the region.

Late spring offers comfortable temperatures, typically ranging from 15°C to 25°C, making it ideal for walking, visiting local farms, and enjoying the natural beauty of the Hudson Valley. The foliage is lush and green, and many local attractions, such as farmers' markets and outdoor events, begin to open for the season. This period is particularly good for solo travellers or couples looking for a relaxed getaway with opportunities for scenic drives and light outdoor recreation without the peak summer crowds.

Early autumn provides a spectacular display of fall colours, especially from late September through October, with temperatures usually between 10°C and 20°C. This is a prime time for couples or solo travellers who appreciate picturesque landscapes and outdoor activities like apple picking at local orchards or exploring nearby state parks. The crisp air and vibrant scenery make it a popular time for wine tasting tours at local vineyards.

While summer (July to August) is also a popular time with warmer weather for lakes and outdoor adventures, it can be busier and hotter.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to 'My Trips' and selecting your reservation. To find flexible deals, filter your search by 'Fully refundable property' for hotels in Chester.
How can I save on a hotel booking in Chester with Expedia?
One Key™—Expedia's free travel rewards programme—gives you instant access to discounts with Member Prices on Chester hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Chester?
Prices for hotels in Chester often vary, but you can find a great deal from NZ$168 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by 'Price: low to high' for our cheapest rates.

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