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Compare 974 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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."
$73 nightly
The price is $86
Sep 14 - Sep 15
Total with taxes and fees
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 "
$116 nightly
The price is $137
Sep 7 - Sep 8
Total with taxes and fees
Candlewood Suites Middletown Goshen by IHG

Sleep Inn & Suites Middletown - Goshen

2.5 star property
8.4 out of 10, Very Good, (1026)
"great stay"
$102 nightly
The price is $121
Sep 28 - Sep 29
Total with taxes and fees
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 "
$134 nightly
The price is $158
Sep 2 - Sep 3
Total with taxes and fees
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,"
$215 nightly
The price is $243
Sep 4 - Sep 5
Total with taxes and fees
The Dominion House Bed & Breakfast

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3.0 star property
9.4 out of 10, Exceptional, (815)
"Place was great have stayed here many times."
$127 nightly
The price is $150
Sep 7 - Sep 8
Total with taxes and fees
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, (1013)
"Great hotel!"
$115 nightly
The price is $130
Sep 2 - Sep 3
Total with taxes and fees
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 "
$84 nightly
The price is $104
Sep 21 - Sep 22
Total with taxes and fees
Americas Best Value Inn at Central Valley-Woodbury

Sleep Inn & Suites Monroe - Woodbury

2.5 star property
9.4 out of 10, Exceptional, (1013)
"great place to stay"
$113 nightly
The price is $127
Sep 7 - Sep 8
Total with taxes and fees
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"
$75 nightly
The price is $86
Sep 2 - Sep 3
Total with taxes and fees
Appalachian Motel

High Point Motel

2.0 star property
8.8 out of 10, Excellent, (65)
"Peaceful and a nice views staff was very friendly and nice definitely will return"
$80 nightly
The price is $90
Sep 14 - Sep 15
Total with taxes and fees
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!"
$101 nightly
The price is $124
Sep 28 - Sep 29
Total with taxes and fees
Fairfield Inn & Suites by Marriott Goshen Middletown

The Crossroads Hotel, Newburgh

3.0 star property
7.4 out of 10, Good, (531)
"Had a good time there "
$93 nightly
The price is $109
Sep 2 - Sep 3
Total with taxes and fees
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 ."
$134 nightly
The price is $151
Sep 15 - Sep 16
Total with taxes and fees
Harvest Inn

Hampton Inn by Hilton Middletown

2.5 star property
8.6 out of 10, Excellent, (1010)
"Nice hotel"
$105 nightly
The price is $125
Sep 14 - Sep 15
Total with taxes and fees
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."
$99 nightly
The price is $112
Sep 28 - Sep 29
Total with taxes and fees
Days Inn by Wyndham Wurtsboro

Overlook Lodge at Bear Mountain

2.5 star property
8.4 out of 10, Very Good, (1018)
"Quiet cabin/room and lovely grounds around the lake; easy hiking in the area. "
$131 nightly
The price is $149
Sep 14 - Sep 15
Total with taxes and fees
Overlook Lodge at Bear Mountain

Courtyard by Marriott Middletown Goshen

3.0 star property
8.6 out of 10, Excellent, (978)
"Great location for a trip to Legoland. Convenient, clean and close to good food options."
$101 nightly
The price is $119
Sep 7 - Sep 8
Total with taxes and fees
Courtyard by Marriott Middletown Goshen

Quality Inn & Suites Fishkill South near I-84

2.5 star property
8.8 out of 10, Excellent, (1021)
"Good place to stay"
$99 nightly
The price is $112
Sep 14 - Sep 15
Total with taxes and fees
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 "
$100 nightly
The price is $113
Sep 7 - Sep 8
Total with taxes and fees
Holiday Inn Express & Suites Montgomery by IHG
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

Top Chester Hotel Reviews

More cheap stays in Chester

More cheap stays in Chester

Hotels in Chester with star-rating

Hotels in Chester with star-rating

Find out more about Chester

Find out more about Chester

Top reasons to visit Chester

  • Outdoor Adventures: Chester is perfect for hiking, exploring national and state parks, and enjoying beautiful lakes.
  • Family-Friendly Attractions: The area offers a variety of entertainment options suitable for all ages.
  • Vibrant Events: Chester hosts numerous festive events throughout the year, adding local charm to your visit.
  • Charming Atmosphere: Experience the serene landscapes and friendly community, ideal for relaxation.
  • Diverse Accommodations: Chester provides a range of lodging options, from pet-friendly to family-oriented stays.

Find great hotels near Chester

Discover a variety of lodging options in Chester, New York, catering to all types of travelers. Whether you're seeking pet-friendly accommodations, family-friendly experiences, or business-focused amenities, Chester has something for everyone. Explore the best hotels in the area to find the perfect fit for your vacation, complete with helpful hotel reviews to guide your choice.

  • Super 8 by Wyndham Middletown: Super 8 by Wyndham Middletown offers a cozy and budget-friendly motel experience, located 9 miles away from Chester. This property caters to travelers looking for a straightforward stay without sacrificing comfort. Guests can kick-start their day with a complimentary breakfast and unwind while enjoying entertainment options like satellite TV and premium channels. Nearby outlets provide easy shopping opportunities, making it a convenient choice for leisure travelers and families alike.
  • Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point: Located 14 miles from Chester, Red Roof Inn & Suites is an inclusive and family-friendly hotel that warmly welcomes LGBTQIA guests and their furry friends. This property features a variety of amenities designed for families, including free cribs, and a pet-friendly policy that allows dogs and cats. The hotel’s commitment to ensuring a comfortable stay for all types of travelers makes it an ideal choice for those seeking a relaxed environment with a personal touch.
  • Howard Johnson by Wyndham Newburgh/West Point: Situated 14 miles from Chester, Howard Johnson by Wyndham is perfect for business travelers seeking a productive stay. This hotel offers essential services and facilities tailored for corporate needs, ensuring guests can conduct business efficiently while enjoying a comfortable atmosphere. With its convenient location and business-friendly amenities, it’s a top choice for professionals looking to balance work and leisure during their visit.

Where to stay near Chester

Chester, New York, offers a delightful blend of charm and convenience for families and leisure travelers alike. Explore the serene landscapes and friendly atmosphere while enjoying low crowds in this picturesque city. Discover the best spots for relaxation, outdoor activities, and local dining. Nearby attractions provide a budget-friendly escape, ensuring a memorable vacation experience filled with friendly people and a welcoming vibe. Chester is truly a hidden gem waiting to be explored.

  • Middletown: Located approximately 10 miles from Chester, Middletown is a vibrant city that offers a blend of family-friendly activities and entertainment options. Visitors can enjoy a variety of attractions including a theme park and beautiful lakes, making it ideal for those looking to create lasting memories. The shopping centers and malls cater to retail enthusiasts, while the city's resorts provide a relaxing getaway. With peak travel seasons in April and from June to July, it’s a great spot to experience city life intertwined with leisure.
  • Goshen: Just 4 miles from Chester, Goshen is a charming city that draws travelers seeking family-oriented and entertainment-themed experiences. With a modern square at its heart, visitors can explore shops and enjoy the bustling atmosphere. The town’s proximity to a theme park and various resorts adds to its appeal, especially during peak travel times in March and July. Whether you're looking for a quick shopping trip or a fun family day out, Goshen offers a delightful mix of activities.
  • Monroe: Situated 5 miles away from Chester, Monroe is a lively city that caters to both families and business travelers. Its shopping centers and malls provide ample opportunities for retail therapy, while the nearby theme park, lake, and mountains offer exciting recreational activities. The travel experience peaks in the summer months, particularly from June to July and September, making it a popular destination. Whether you're on a family vacation or a business trip, Monroe has something for everyone.

Things to do in and around Chester

Chester, New York, is a fantastic destination for family-friendly vacations and entertainment seekers. Visitors can enjoy a range of activities, including exploring local resorts, shopping at the mall center, and participating in festive events. Don’t miss the vibrant event calendars and typical sightseeing opportunities that showcase the area’s charm. For outdoor enthusiasts, hiking essentials are readily available, making Chester a perfect blend of relaxation and adventure.

Shopping

In Chester, you can explore Monroe Federal Plaza Shopping Center, only 6 miles away, for a vibrant shopping experience. Soons Orchards, 7 miles away, offers local produce and unique gifts. Old Glory Mall Shopping Center, 8 miles away, combines entertainment and shopping for the whole family.

Recreation

Experience the energetic atmosphere at The Rock Sports Complex, where you can engage in various sports activities. For a touch of luxury, visit The Golf Club at Mansion Ridge, offering exquisite golfing experiences. Unwind at Thomas Bull Memorial Park, a perfect spot for relaxation and rejuvenation in nature.

Adventure

Experience the thrill of motor racing at Orange County Fair Speedway, located 9 miles from Chester, where adrenaline and excitement reign. Enjoy skiing at Mount Peter Ski Area, 8 miles away, or explore the scenic Continental Road Trailhead, also 8 miles from Chester, perfect for outdoor adventures.

Nightlife

Experience the vibrant nightlife in Chester at Castle Fun Center, where adventure awaits in their arcade. For a touch of culture and romance, catch a show at Paramount Theatre or Ritz Theater, both offering family-friendly entertainment just a short drive away.

*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, is a budget-friendly destination with plenty of free activities, like exploring Sterling Forest State Park. To save on accommodations, plan your trip between January and March when prices are lower, and aim for a Tuesday stay for the best rates. Utilize Expedia to find the best hotel deals by filtering prices from lowest to highest, and consider booking a package to combine your hotel, flights, and activities for additional savings. Join the One Key membership for exclusive discounts and earn OneKeyCash for future stays.

  • 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: Utilize Expedia's search tool to refine your preferences, such as your budget, desired location, and preferred hotel type. To find the best prices and deals, 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 by purchasing an Expedia package.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Chester

Chester, New York, is an ideal destination for family fun and entertainment-themed vacations. Visitors can explore a variety of attractions, including national and state parks, beautiful lakes, and urban parks. These points of interest offer outdoor adventures, cultural experiences, and stunning scenery, catering to travelers seeking both relaxation and excitement. No matter your interests, Chester promises a memorable getaway for everyone.

  • United States Military Academy: Located 14 miles from Chester, this prestigious military academy offers a glimpse into American military history and training. Visitors can explore the stunning campus, take guided tours, and admire the picturesque views of the Hudson River.
  • Bear Mountain State Park: Just 15 miles away, Bear Mountain State Park is a haven for outdoor enthusiasts. With its scenic hiking trails, breathtaking views, and opportunities for picnicking and wildlife watching, it's perfect for adventure seekers and nature lovers alike.
  • Harness Racing Museum and Hall of Fame: Situated only 4 miles from Chester, this museum celebrates the rich history of harness racing. Enjoy interactive exhibits and engaging displays that showcase the sport's culture and significance in American history.

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.

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 your visit to Chester, New York, you have several major airports to choose from. John F. Kennedy International Airport (JFK) is located 56 miles away, with excellent nearby hotels like Arlo Williamsburg and The William Vale, both 11 miles from JFK. Newark Liberty International Airport (EWR) is 47 miles away, featuring luxury accommodations such as The Dominick and The Wall Street Hotel, both 9 miles from EWR. LaGuardia Airport (LGA) is the closest at 46 miles, with upscale options like Virgin Hotels New York City and The Mark, both just 6 miles from LGA. Each airport offers convenient access to Chester for a smooth travel experience.

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 travelers seeking a serene yet engaging experience in Chester, New York. This picturesque neighborhood is surrounded by the natural beauty of the Hudson Valley, providing a peaceful retreat while still being conveniently located near local attractions. Visitors can enjoy scenic hikes, charming boutique shops, and delightful eateries that celebrate the region's vibrant culinary scene.

For couples looking for a romantic escape, Blooming Grove's tranquil atmosphere and stunning landscapes make it superb for intimate getaways. Imagine sharing a bottle of local wine while watching the sun set over the rolling hills, or taking a leisurely stroll through the nearby parks, where the beauty of nature complements your special moments together.

Families will also find Blooming Grove appealing, as it offers a range of outdoor activities suitable for all ages. Whether it's exploring nearby hiking trails or enjoying a picnic in one of the local parks, there are ample opportunities to create lasting memories. The area's friendly community and family-friendly amenities ensure a welcoming environment for everyone.
What are the best budget hotels in Chester?
The Holiday Inn Express Hotel & Suites Chester by IHG is a fantastic option for travelers 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 July. This is when the city comes alive with vibrant festivals and a range of outdoor activities. With temperatures typically ranging from the mid-60s to low 70s Fahrenheit, the weather is pleasantly warm, inviting visitors to explore Chester's picturesque streets and historical landmarks.

During the peak season from July to September, Chester experiences a flourishing atmosphere, making it an ideal time for those who appreciate engaging cultural experiences. The city's renowned attractions, such as the stunning Chester Cathedral and the iconic Rows, are bustling with energy, great for those who enjoy a lively environment. To enhance your visit, consider booking guided tours in advance, ensuring that you can fully enjoy the sights without the hassles of long lines.

For outdoor enthusiasts, July is particularly appealing. The city's parks, such as Grosvenor Park, offer beautifully maintained gardens and scenic walking paths, great for leisurely strolls. Additionally, the nearby River Dee provides opportunities for boat trips and riverside picnics, allowing you to soak up the sun while appreciating the surrounding nature.

If you're seeking a quieter experience, consider visiting Chester in November. This month often presents lower accommodation rates and fewer crowds, giving you the chance to explore at a leisurely pace. The city is also beautifully decorated for the holiday season, adding a festive charm to your visit.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 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 Chester hotel booking with Expedia?
One Key™ - Expedia's free travel rewards program - gives you instant access to perks and 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.

*OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
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 $95 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.