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Top 10 Chester hotels and places to stay

Our top choices for Chester hotels

Super 8 by Wyndham Middletown

2.5 star property
6.2 out of 10, (1013)
"I had a wonderful stay and hope to see you again soon."
The price is £64
includes taxes & fees
7 Sept - 8 Sept
Super 8 by Wyndham Middletown

Candlewood Suites Middletown Goshen by IHG

2.5 star property
8.4 out of 10, Very good, (22)
"The hotel was amazing keep up the good work "
The price is £102
includes taxes & fees
7 Sept - 8 Sept
Candlewood Suites Middletown Goshen by IHG

Sleep Inn & Suites Middletown - Goshen

2.5 star property
8.4 out of 10, Very good, (1025)
"Great stay"
The price is £90
includes taxes & fees
28 Sept - 29 Sept
Sleep Inn & Suites Middletown - Goshen

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 star property
8.4 out of 10, Very good, (1009)
"Great staff and rooms "
The price is £117
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn Express Hotel & Suites Chester by IHG

The Dominion House Bed & Breakfast

2.0 star property
9.2 out of 10, Wonderful, (229)
"Amazing hospitality,"
The price is £180
includes taxes & fees
2 Sept - 3 Sept
The Dominion House Bed & Breakfast

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3.0 star property
9.4 out of 10, Exceptional, (814)
"Place was great have stayed here many times."
The price is £109
includes taxes & fees
1 Sept - 2 Sept
La Quinta Inn & Suites by Wyndham Middletown-Goshen

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2.0 star property
8.4 out of 10, Very good, (1011)
"Great hotel!"
The price is £96
includes taxes & fees
1 Sept - 2 Sept
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Americas Best Value Inn at Central Valley-Woodbury

2.0 star property
7.0 out of 10, Good, (1008)
"nice place to stay in "
The price is £82
includes taxes & fees
1 Sept - 2 Sept
Americas Best Value Inn at Central Valley-Woodbury

Sleep Inn & Suites Monroe - Woodbury

2.5 star property
9.4 out of 10, Exceptional, (1011)
"great place to stay"
The price is £94
includes taxes & fees
3 Sept - 4 Sept
Sleep Inn & Suites Monroe - Woodbury

Appalachian Motel

2.0 star property
7.6 out of 10, Good, (496)
"This is a privately owned hotel the manager didn't bother you It was a quiet place very clean however be careful turning into the driveway it's a very sharp turn but overall it was a great stay and a great value"
The price is £57
includes taxes & fees
1 Sept - 2 Sept
Appalachian Motel

High Point Motel

2.0 star property
8.8 out of 10, Excellent, (64)
"Peaceful and a nice views staff was very friendly and nice definitely will return"
The price is £73
includes taxes & fees
1 Sept - 2 Sept
High Point Motel

Fairfield Inn & Suites by Marriott Goshen Middletown

2.5 star property
8.8 out of 10, Excellent, (1005)
"Great place to stay when you’re in need of relaxation and some family time!"
The price is £92
includes taxes & fees
28 Sept - 29 Sept
Fairfield Inn & Suites by Marriott Goshen Middletown

The Crossroads Hotel, Newburgh

3.0 star property
7.4 out of 10, Good, (530)
"Had a good time there "
The price is £81
includes taxes & fees
2 Sept - 3 Sept
The Crossroads Hotel, Newburgh

Harvest Inn

2.5 star property
9.4 out of 10, Exceptional, (552)
"Lovely hotel with wonderful staff. Very close to great dining eg Classic diner and Pine Bush Chinese . It’s positioned in a lovely area and has a very nice outdoor seating area where you can sit outside and enjoy the sun sets . I removed one star as the air conditioner in our room was very noisy with a musty smell but everything else was perfect ."
Harvest Inn

Hampton Inn by Hilton Middletown

2.5 star property
8.6 out of 10, Excellent, (1009)
"Property was clean and staff was friendly. "
The price is £92
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn by Hilton Middletown

Days Inn by Wyndham Wurtsboro

2.0 star property
7.6 out of 10, Good, (541)
"The staff was helpful. The location was convenient. The room was clean."
The price is £83
includes taxes & fees
28 Sept - 29 Sept
Days Inn by Wyndham Wurtsboro

Overlook Lodge at Bear Mountain

2.5 star property
8.4 out of 10, Very good, (1018)
"3rd stay at this cottage and we love it. Will definitely be staying here in the future "
The price is £113
includes taxes & fees
3 Sept - 4 Sept
Overlook Lodge at Bear Mountain

Courtyard by Marriott Middletown Goshen

3.0 star property
8.6 out of 10, Excellent, (976)
"Great location for a trip to Legoland. Convenient, clean and close to good food options."
The price is £88
includes taxes & fees
7 Sept - 8 Sept
Courtyard by Marriott Middletown Goshen

Quality Inn & Suites Fishkill South near I-84

2.5 star property
8.8 out of 10, Excellent, (1020)
"Good place to stay"
The price is £83
includes taxes & fees
14 Sept - 15 Sept
Quality Inn & Suites Fishkill South near I-84

Holiday Inn Express & Suites Montgomery by IHG

2.5 star property
8.8 out of 10, Excellent, (759)
"Super clean and breakfast was amazing "
The price is £84
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Express & Suites Montgomery by IHG
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Accommodation near Chester attractions

The Rock Sports Complex

The Rock Sports Complex

Explore the great outdoors at The Rock Sports Complex, a lovely green space in Chester. While you're in the area, find time to visit its shops.

Top Chester Hotel Reviews

More cheap stays in Chester

More cheap stays in Chester

Find out more about Chester

Find out more about Chester

Top reasons to visit Chester

  • Stunning Outdoor Adventures: Explore beautiful national and state parks, picturesque lakes, and urban parks, perfect for nature enthusiasts.
  • Family-Friendly Attractions: Chester is packed with activities suitable for all ages, ensuring fun for the entire family.
  • Vibrant Shopping Experiences: Indulge in retail therapy at local shopping centres and malls, offering a wide range of options.
  • Warm Local Hospitality: Enjoy the charm and friendliness of the locals, enhancing your travel experience.
  • Diverse Accommodation Options: Choose from family-friendly hotels to luxury stays, catering to all types of travellers.

Find great hotels near Chester

Discover the charm of Chester, New York, with a variety of accommodation options that cater to every type of traveller. From family-friendly hotels to pet-friendly lodgings, the area offers a warm welcome for all. Whether you're seeking a business-themed stay or a relaxing getaway, Chester's hotels promise comfort and convenience, ensuring a delightful experience during your visit.

  • Super 8 by Wyndham Middletown: A convenient and budget-friendly lodging option, Super 8 by Wyndham Middletown is situated a mere 5.6km from Chester. This motel is ideal for travellers seeking a straightforward stay with essential amenities. Guests can start their day with complimentary breakfast options available on weekdays and weekends, including wrapped food for those on the go. The property boasts entertainment features such as premium TV channels, satellite TV, and a television in each room. With nearby outlet shopping, it's perfect for those looking to explore local attractions.
  • Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point: Located 8.7km from Chester, the Red Roof Inn & Suites Newburgh offers a welcoming atmosphere for families and business travellers alike. This hotel prides itself on being LGBTQIA-friendly and provides a selection of amenities tailored for business needs, including a meeting room and business centre. Families will appreciate the complimentary cribs available for younger guests. With its commitment to inclusivity and comfort, this property is a fantastic choice for diverse groups looking for a pleasant stay near the scenic Hudson Valley.
  • Howard Johnson by Wyndham Newburgh/West Point: Positioned 8.7km from Chester, the Howard Johnson by Wyndham Newburgh is an excellent choice for business-minded travellers. This hotel features a range of facilities designed to support corporate needs, ensuring a productive stay. With a focus on comfort and convenience, guests can take advantage of spacious accommodations and essential amenities, making it a suitable base for those visiting the West Point area or conducting business in Newburgh.

Where to stay near Chester

Chester, New York, offers a delightful blend of family-friendly attractions and vibrant city life. Discover the picturesque scenery as you explore nearby towns and enjoy the warm hospitality of the locals. Ideal for both budget-conscious travellers and those seeking luxury, Chester serves as a perfect base to experience the charm of New York City and its popular destinations. From entertainment to relaxation, this friendly city promises a memorable getaway for all.

  • Middletown: Situated approximately 6.2km from Chester, Middletown is a vibrant city offering a mix of family-friendly entertainment and urban experiences. While its visitor numbers remain fairly consistent throughout the year, the peak months of April and June to July see an influx of tourists eager to explore its array of attractions. From shopping centres to resorts, there's something for everyone. Local highlights include a lively theme park and picturesque lakes, perfect for a day out with family or friends. With its bustling atmosphere, Middletown invites you to immerse yourself in a truly enjoyable city-themed experience.
  • Goshen: Located a mere 2.5km from Chester, Goshen is a charming city that draws visitors year-round, with notable peaks in March, July, and September. Known for its family-friendly vibe and entertainment options, Goshen boasts a range of shopping centres and resorts. The city is also home to a delightful tourist precinct and a vibrant town square, making it an excellent spot for leisurely strolls and dining experiences. Whether you're looking to shop or simply enjoy the local culture, Goshen offers a welcoming atmosphere and unique attractions that are sure to delight.
  • Monroe: Just 3.1km from Chester, Monroe is a city that combines business and leisure, appealing to a diverse range of travellers. The peak visitor months of June to July and September highlight its attractiveness as a destination. Popular for its shopping malls and resorts, Monroe also features stunning natural landmarks, including lakes and mountains, making it perfect for outdoor enthusiasts. With a family-oriented vibe and a variety of activities on offer, Monroe provides a balanced travel experience that caters to both relaxation and adventure.

Things to do in and around Chester

Chester offers a delightful mix of family-friendly activities and city-themed attractions. Visitors can enjoy a relaxing stay at local resorts, explore vibrant shopping centres, and indulge in retail therapy at the shopping mall. With its variety of entertainment options, Chester is an ideal destination for a memorable holiday experience.

Shopping

For a delightful shopping experience in Chester, visit Monroe Federal Plaza Shopping Center, just 3.7km away, offering a vibrant atmosphere. Soons Orchards, located 4.3km away, provides a charming market feel. If you're up for a drive, Harriman Plaza Shopping Center, also 4.3km away, awaits with more family-friendly options.

Recreation

Experience the vibrant atmosphere at The Rock Sports Complex, where you can engage in various sports activities. Indulge in luxury at The Golf Club at Mansion Ridge, offering exquisite surroundings for a round of golf. For more sports excitement, visit Michie Stadium, known for its energetic vibe.

Adventure

Experience the thrill of motor racing at Orange County Fair Speedway, located 5.6km from Chester, where the adrenaline rush meets a vibrant atmosphere. Alternatively, enjoy skiing at Mount Peter Ski Area, 5.0km away, or explore the scenic Continental Road Trailhead, also 5.0km from Chester, for outdoor adventures.

Nightlife

For a lively night in Chester, visit Castle Fun Center for family-friendly arcade fun. Just 6.2km away, the Paramount Theatre offers a charming blend of culture and romance. For thrill-seekers, the Alpine Mountain Coaster, located 10.6km away, promises an exhilarating ride under the stars.

Booking tips and Expedia advantages for Chester

Chester, New York, offers numerous ways to save during your visit. Enjoy free entry to attractions like Sterling Forest State Park and explore the town without spending a penny. For budget-friendly accommodation, consider visiting between January and March, with Tuesday being the cheapest day to stay. Use Expedia to compare prices and find eco-certified hotels, and take advantage of package deals that combine flights and activities for better savings. Remember to filter prices from lowest to highest for the best rates available.

  • 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 July to August and 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 selections based on your budget, preferred location, and desired hotel type. For instance, selecting the Eco-certified option will showcase sustainable and environmentally friendly hotels that are currently available. To discover the best prices and offers, simply arrange the price filter from lowest to highest.
  • 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 near Chester

Chester, New York, is an ideal destination for families and those seeking entertainment or urban experiences. Visitors can explore stunning national and state parks, picturesque lakes, and urban parks, all offering a mix of outdoor adventures, scenic beauty, and cultural experiences. With a variety of attractions to discover, Chester promises an enjoyable getaway for all travellers looking to immerse themselves in nature and local charm.

  • Bear Mountain State Park: Located 9.3km from Chester, this national park offers a stunning blend of adventure and outdoor activities. You can hike scenic trails, enjoy breathtaking views of the Hudson River, and experience the natural beauty that makes this park a haven for nature enthusiasts.
  • Storm King Art Center: Just 7.5km away, this renowned arts centre features expansive outdoor installations set against a picturesque landscape. The combination of large-scale sculptures and rolling hills provides a unique cultural experience that celebrates both art and nature.
  • Harriman State Park: Situated 8.1km from Chester, this state park is steeped in history and offers a variety of recreational opportunities. Explore its rich heritage through hiking, picnicking, and discovering the remnants of old estates amidst the lush woodlands.

Best time to go to Chester

The best time to visit Chester is dependant 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.

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 HighSlightly High
August72.0°F (22.2°C)Light RainMostly SunnyAverageSlightly High
September64.9°F (18.3°C)Light RainMostly SunnySlightly HighAverage
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 planning a visit to Chester, New York, you have several major airports to consider. John F. Kennedy International Airport (JFK) is situated 34.8km away, with nearby hotels such as the luxurious Arlo Williamsburg and The William Vale, both 6.8km from the airport. Newark Liberty International Airport (EWR) is 29.2km from Chester, offering upscale options like The Dominick and 33 Hotel, both located 5.6km away. LaGuardia Airport (LGA) is the closest at 28.6km, featuring top-rated accommodations like Virgin Hotels New York City and Hilton Club The Quin, both 3.7km from the airport, ensuring convenient access to your travel needs.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What is the best area to stay in Chester?
Blooming Grove is the ideal area to stay for travellers seeking a blend of tranquility and convenience in New York. Nestled amidst scenic landscapes, this charming neighbourhood offers a peaceful retreat while still being just a short drive from the vibrant attractions of the Hudson Valley. With its picturesque parks and outdoor activities, Blooming Grove is great for those who appreciate nature without sacrificing accessibility to urban adventures.

For couples, Blooming Grove provides a serene atmosphere great for a romantic getaway. Imagine enjoying leisurely strolls through lush greenery or picnicking by the lakeside, creating a great backdrop for intimate moments together. The nearby wineries and quaint local restaurants offer delightful opportunities to indulge in fine dining or wine tasting, adding to the romantic experience.

Families will also find Blooming Grove appealing, as it boasts a range of outdoor activities that cater to children of all ages. The local parks feature playgrounds and spacious areas for recreational activities, ensuring that young ones remain entertained. Plus, the proximity to family-friendly attractions in the Hudson Valley means there's always something new to explore.
What are the best budget hotels in Chester?
The Holiday Inn Express Hotel & Suites Chester by IHG is a fantastic option for travellers seeking budget-friendly accommodations without compromising on quality. With an excellent review score of 8.6, this hotel offers a warm and friendly setting, superb for families and couples alike. View all budget hotels in Chester.
When is the best time to go to Chester?
The most popular time to visit Chester is during the summer months, particularly in July. At this time, the city comes alive with vibrant festivals and events, while the weather typically ranges from 17 to 22°C, making it superb for exploring the historic streets and picturesque riverside.

From July to September, Chester experiences its high tourist season, attracting visitors keen to discover its unique blend of Roman history and medieval architecture. The city's charming shops, delightful cafés, and the famous Chester Zoo are bustling with activity, creating an energetic atmosphere ideal for families and couples alike. The pleasant climate encourages outdoor activities, allowing you to enjoy leisurely walks along the River Dee or through the beautiful Grosvenor Park.

For those who prefer a quieter experience, consider visiting in November. This month offers a unique charm, with fewer crowds and the opportunity to enjoy the city's rich history and cultural offerings at a more leisurely pace. You can explore the iconic Chester Rows or visit the stunning Chester Cathedral, all while enjoying the beautiful autumn scenery.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Chester hotel for you.
How can I save on a Chester hotel booking with Expedia?
With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Chester hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings.
How much is the nightly rate at a Chester hotel?
Prices for hotels in Chester often vary, but you can find a great deal from £57 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 the cheapest rate.