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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 Rp1.754.245
Rp2.159.915 total
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 Rp3.883.330
Rp4.393.040 total
includes taxes & fees
16 Nov - 17 Nov
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, (1,127 reviews)
"Great stay, thanks"
United States
Gina
The price is Rp2.055.722
Rp2.325.535 total
includes taxes & fees
22 Nov - 23 Nov
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, (1,000 reviews)
"Clean rooms, nice staff, and convenience to Lego Land"
United States
Aeron
The price is Rp2.329.998
Rp2.868.810 total
includes taxes & fees
12 Nov - 13 Nov
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 Rp1.610.010
Rp4.267.280 total
includes taxes & fees
20 Nov - 21 Nov
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, (1,151 reviews)
"Close to restaurants and shopping, grocery store close as well."
United States
Timothy
The price is Rp2.013.765
Rp2.479.449 total
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn Harriman Woodbury

7. 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 Rp1.534.693
Rp1.812.856 total
includes taxes & fees
29 Nov - 30 Nov
Tru by Hilton Middletown

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 Rp2.044.509
Rp2.415.077 total
includes taxes & fees
6 Dec - 7 Dec
La Quinta Inn & Suites by Wyndham Middletown-Goshen

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 Rp1.733.952
Rp2.048.230 total
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express & Suites Middletown - Goshen by IHG

10. 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 Rp1.903.735
Rp2.248.787 total
includes taxes & fees
19 Nov - 20 Nov
Courtyard by Marriott Middletown Goshen

11. 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 Rp2.748.133
Rp3.309.450 total
includes taxes & fees
25 Nov - 26 Nov
Home2 Suites by Hilton Middletown

12. 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 Rp4.321.333
Rp5.320.643 total
includes taxes & fees
10 Dec - 11 Dec
The Orange Inn Boutique Hotel

13. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,255 reviews)
"Great stay"
Canada
Justine
The price is Rp1.928.299
Rp2.277.804 total
includes taxes & fees
10 Dec - 11 Dec
Sleep Inn & Suites Middletown - Goshen

14. 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 Rp2.080.742
Rp2.561.912 total
includes taxes & fees
12 Nov - 13 Nov
Parkway House Goshen Family-Friendly Bed & Breakfast

15. 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 Rp2.015.392
Rp2.481.452 total
includes taxes & fees
15 Nov - 16 Nov
Comfort Suites Central Valley - Woodbury

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 Rp1.581.328
Rp1.867.944 total
includes taxes & fees
10 Dec - 11 Dec
Hampton Inn by Hilton Middletown

17. Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1,017 reviews)
"Great place, but was super crowded."
United States
Mike P
The price is Rp2.099.669
Rp2.480.233 total
includes taxes & fees
29 Nov - 30 Nov
Overlook Lodge at Bear Mountain

18. 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 Rp1.788.138
Rp2.201.577 total
includes taxes & fees
12 Nov - 13 Nov
Americas Best Value Inn at Central Valley-Woodbury

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 Rp2.041.006
Rp2.410.916 total
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express & Suites Montgomery by IHG

20. 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 Rp1.673.444
Rp1.976.756 total
includes taxes & fees
15 Nov - 16 Nov
Microtel Inn & Suites by Wyndham Middletown
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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

More cheap stays in Chester

Find out more about Chester

Top reasons to visit Chester

  • Family-Friendly Attractions: Chester boasts a variety of family-oriented activities, from the Chester Zoo to local parks, ensuring fun for all ages.
  • Charming City Centre: Stroll through the delightful city centre filled with friendly locals, shops, and eateries that reflect the town's vibrant character.
  • Picturesque Countryside: The beautiful Cheshire countryside offers serene landscapes, perfect for leisurely walks and outdoor activities.
  • Diverse Accommodation: Chester provides a range of lodging options, from cosy hotels to agritourism properties, catering to various needs and preferences.
  • Unique Leisure Experiences: Enjoy local leisure centres and a distinctive cinema experience for relaxation and entertainment during your stay.

Find great hotels near Chester

Discover a range of delightful accommodation options in Chester, New York, where you'll find hotels that cater to business travellers, families, and pet owners alike. With an emphasis on comfort and a welcoming atmosphere, these lodgings provide the perfect base for exploring the area. Whether you're seeking a cosy hotel or an agritourism property, Chester offers a variety of choices to suit your needs.

  • Super 8 by Wyndham Middletown: Nestled just 14km from Chester, Super 8 by Wyndham Middletown offers a budget-friendly motel experience ideal for travellers seeking comfort without breaking the bank. Guests can unwind in rooms equipped with premium TV channels, satellite TV, and standard televisions, ensuring entertainment options are at hand. The motel’s proximity to nearby outlets allows for an engaging shopping experience, making it a practical choice for those who appreciate accessibility to local attractions.
  • Howard Johnson by Wyndham Newburgh/West Point: Located 23km away from Chester, Howard Johnson by Wyndham Newburgh/West Point provides a budget-conscious lodging option tailored for business travellers. This hotel features essential amenities catering to those on professional trips, ensuring a seamless stay. With a focus on convenience and practicality, it is an ideal choice for guests looking to balance work commitments with relaxation.
  • Hampton Inn Harriman Woodbury: Situated a mere 13km from Chester, the Hampton Inn Harriman Woodbury boasts an impressive guest rating of 9.2 out of 10. This welcoming hotel is conducive for both pet owners and business travellers, offering a pet-friendly environment with specific policies in place. Guests can enjoy comfortable accommodations alongside a range of amenities tailored to enhance their stay, making this property a top choice for those seeking a friendly and efficient experience.

Where to stay near Chester

Chester, New York, offers a delightful blend of family-friendly activities and vibrant city life. Explore the charming city centre, where friendly locals welcome you to an array of shops and eateries. Just a stone's throw away, the picturesque Cheshire countryside beckons with its serene landscapes. Whether you're seeking a leisurely shopping experience or a luxurious retreat, Chester provides the perfect backdrop for your memorable vacation.

  • Middletown: Situated approximately 16km from Chester, Middletown is a vibrant city that offers a diverse range of experiences for travellers. Known for its family-friendly atmosphere, visitors flock here for city-themed entertainment, particularly during the peak months of April and June to July. The area boasts a variety of popular venues, including resorts and shopping centres, ensuring ample opportunities for leisure and retail therapy. Notable local landmarks, such as a theme park and a lively tourist precinct, make Middletown a delightful destination for families and anyone seeking a fun-filled day out.
  • Goshen: Located a mere 6km from Chester, Goshen is a charming city known for its welcoming environment and diverse entertainment options. Visitors are drawn to Goshen for its family-friendly and city-themed experiences, with peak travel seasons occurring in March, July, and September. The city's attractions include shopping malls and resorts, making it ideal for those looking to indulge in some retail therapy or relaxation. Local highlights, such as a theme park and an inviting tourist precinct, provide a perfect backdrop for creating memorable experiences with loved ones.
  • Monroe: Just 8km from Chester, Monroe presents a delightful mix of family, city, and business-themed experiences. The city sees a rise in traveller numbers during June to July and September, making it a popular choice for quick getaways. Monroe offers numerous shopping centres and a ski area for winter sports enthusiasts. Moreover, its proximity to local attractions like a theme park, scenic lakes, and majestic mountains makes Monroe an excellent choice for those looking to explore the great outdoors while enjoying urban conveniences.

Things to do near Chester

Shopping

In Chester, you can explore charming local shops for unique souvenirs. If you're up for a drive, head to the Woodbury Common Premium Outlets, offering a variety of designer brands, or the Galleria at White Plains for an extensive shopping experience.

Recreation

In Chester, the Mohonk Mountain House offers a serene environment with its spa featuring treatments inspired by nature. Nearby, the Minnewaska State Park Preserve invites you to explore scenic trails and tranquil lakes, allowing for relaxation amidst stunning landscapes.

Adventure

At the Orange County Fair Speedway, located 14km from Chester, experience the thrill of motor racing amidst an energetic atmosphere. For an exhilarating day outdoors, head to Zoom Ziplines, 27km away, or Palisades Climb Adventure, 40km away, both offering adventurous ziplining experiences in scenic settings.

Nightlife

In Chester, the lively atmosphere at The Chester Theatre offers engaging performances, while local pubs like The Black Bear provide a cosy setting for socialising with friends. For a relaxed evening, the nearby wine bars feature exquisite selections, making for a delightful night out.

*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 for tourists. Enjoy free entry to attractions like Sterling Forest State Park and explore the town at no cost. For accommodation, consider visiting between January and March for lower prices, avoiding the busier August to October period. Tuesdays are typically the cheapest days to stay, while Saturdays are pricier. Use Expedia's search tool to filter by budget and location, and consider booking package deals that combine hotels, flights, and activities for additional 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: Utilise Expedia's search tool to refine your preferences, such as your budget, preferred location, and desired hotel type. To discover the best prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You may find that you can save money by combining your Chester hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions in and around Chester

Chester is ideal for family and entertainment-themed holidays, offering a variety of attractions such as national and state parks, lakes, and urban parks. Visitors can enjoy outdoor activities and cultural experiences while exploring the Chester Zoo, Chester Cathedral, and the famous Chester Racecourse. Additionally, finding suitable accommodation in Liverpool is convenient for those wanting to explore this charming city and its scenic surroundings.

  • Algonquin Park: Located 26km from Chester, Algonquin Park offers a vibrant urban atmosphere, ideal for family outings and outdoor activities. Enjoy leisurely strolls, picnics, and the chance to connect with nature amidst the city’s hustle.
  • National Purple Heart Hall of Honor: Situated 21km away, this military museum is steeped in cultural significance. Visitors can explore the rich history of the Purple Heart and pay tribute to the sacrifices of U.S. military veterans, making it a poignant experience.
  • Goosepond Mountain State Park: Nestled within Chester, this national state park is a haven for outdoor enthusiasts. With stunning scenery and numerous trails, it presents an opportunity for adventure, hiking, and appreciating nature’s beauty.

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

Reaching Chester, New York, is convenient with several major airports nearby. John F. Kennedy International Airport (JFK) is located 90km away, with notable hotels such as The William Vale and Arlo Williamsburg, both 18km from the airport. LaGuardia Airport (LGA) is 74km from Chester, offering luxury options like Hilton Club The Quin and The Plaza, both within 10km. White Plains Airport (HPN) is the closest at 58km, with excellent hotels including The Opus Westchester, only 6km away. Transportation services from these hotels to the airports generally include shuttles and transfers to ensure a smooth journey.

Frequently asked questions

What's the best place to stay in Chester?
Based on our traveller 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 choices for your stay in 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 that most room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to 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 family accommodation 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. Also, children of all ages will enjoy a visit to Castle Fun Center. Find more child-friendly accommodations in Chester.
What is the favourite LGBTQ-friendly accommodation in Chester?
Holiday Inn Express Hotel & Suites Chester by IHG is a top LGBTQ-friendly hotel that features free breakfast and free Wi-Fi. 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 accommodation options 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 will definitely enjoy the shopping and restaurants. Tourists can also enjoy the city's ski areas and coffee shops. A top sight in the area is Woodbury Common Premium Outlets. In Chester, there are 21 hotels and other accommodation options 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. Take a look at what more there is 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 temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Chester are January, February, March and April, with each month seeing an average of 16 cm of snowfall.