Find hotels in Chester, NY from ￥13,504

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Our top choices for Chester hotels

Exterior
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.6 out of 10, Excellent, (1007)
Perfectly positioned for family adventures, this Chester hotel offers free breakfast, WiFi and parking. Take a refreshing swim in the indoor pool after exploring nearby LEGOLAND® or shopping at Woodbury Common Premium Outlets. Clean rooms and attentive staff ensure a comfortable stay.
"The staff was excellent "
United States
Kelley
The price is ￥17,104
￥20,206 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express Hotel & Suites Chester by IHG
Exterior
The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233)
Set in Chester with an inviting outdoor pool, this B&B offers free breakfast and parking. Explore nearby hiking trails or take a short drive to LEGOLAND® New York and Woodbury Common Premium Outlets. The garden and terrace create a peaceful countryside retreat.
"Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY."
United States
Erek
The price is ￥33,430
￥37,818 total
includes taxes & fees
Dec 15 - Dec 16
The Dominion House Bed & Breakfast
Lobby
Quality Inn near Mountain Creek

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (973)
This quiet hotel offers easy access to Mountain Creek Ski Resort and Crystal Springs Golf Resort. Enjoy free breakfast, WiFi, and parking after a day of skiing. The fitness center keeps your routine intact while helpful staff ensures a comfortable mountain getaway.
"Nice hotel. Close to golf,"
United States
Joseph
The price is ￥13,274
￥15,214 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Quality Inn near Mountain Creek
Lobby
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1003)
Experience peaceful accommodations just 10 minutes from LEGOLAND® New York. This Middletown hotel offers a seasonal outdoor pool, fitness center, free breakfast, and parking. Guests praise the helpful staff, clean rooms, and convenient access to Galleria at Crystal Run.
"Room was clean and staff was great!"
United States
Annemarie
The price is ￥12,315
￥14,546 total
includes taxes & fees
Dec 18 - Dec 19
Hampton Inn by Hilton Middletown
Indoor pool, open 8:30 AM to 9:30 PM, sun loungers
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
8.8 out of 10, Excellent, (1001)
Adjacent to a golf course, this serene Nanuet hotel boasts an indoor pool and Windsor Grille for evening dining. The peaceful atmosphere, 24-hour fitness center, and bar create the perfect setting for unwinding near Rockland Bakery and The Shops at Nanuet.
"Great staff, clean and the pool was awesome! "
Canada
Aleah
The price is ￥15,173
￥17,658 total
includes taxes & fees
Jan 4 - Jan 5, 2026
DoubleTree by Hilton Hotel Nanuet
Exterior
Holiday Inn Express & Suites Montgomery by IHG

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, (795)
Located near the train station, this welcoming hotel offers a 24-hour health club and coffee shop. Just minutes from City Winery Hudson Valley and Orange County Farmers Museum, guests appreciate the helpful staff, clean rooms, and free parking.
"Good stay"
United States
Fatima
The price is ￥13,994
￥15,832 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express & Suites Montgomery by IHG
Room, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board
Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1001)
Experience effortless shopping trips with a stay just 10 minutes from Woodbury Common Premium Outlets and LEGOLAND. This hotel offers a fitness center, daily complimentary breakfast, and thoughtful in-room amenities like refrigerators and microwaves.
"Clean and easy check in. "
United States
chris
The price is ￥13,377
￥15,133 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Sleep Inn & Suites Monroe - Woodbury
Suite, 1 King Bed, Non Smoking (1 Bedroom) | In-room safe, desk, iron/ironing board, free cribs/infant beds
Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (593)
"I love "
United States
Niralkumar
The price is ￥15,418
￥17,423 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Days Inn by Wyndham Wurtsboro
Outdoor pool
LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.8 out of 10, Excellent, (33)
Immerse in family fun at this colorful hotel featuring an outdoor pool and restaurant near LEGOLAND® New York. Free breakfast energizes morning adventures, while themed rooms create magical memories. Charles J. Everett Memorial attraction is located nearby.
"We are having a great time at the hotel!!!"
United States
Ziwei
The price is ￥29,596
￥53,853 total
includes taxes & fees
Dec 22 - Dec 23
LEGOLAND Hotel NEW York
Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1001)
Historic lodge near Bear Mountain State Park offers deep-tissue massages and body wraps at the onsite spa. Enjoy drinks at the bar, meals at the café, and rooms with refrigerators and microwaves. Free WiFi and parking add convenience for exploring nearby attractions.
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
The price is ￥15,913
￥18,002 total
includes taxes & fees
Dec 14 - Dec 15
Overlook Lodge at Bear Mountain
Property amenity
Residence Inn by Marriott Fishkill

Residence Inn by Marriott Fishkill

Residence Inn by Marriott Fishkill
3.0 star property
Fishkill
9.4 out of 10, Exceptional, (403)
Step into comfort at this Fishkill hotel with an indoor pool, bar, and 24-hour fitness center. Enjoy complimentary breakfast, WiFi, and parking while staying near Van Wyck Homestead Museum. Business travelers appreciate the helpful staff and convenient amenities.
"Excellent stay!"
United States
Margaret
The price is ￥19,794
￥22,392 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Residence Inn by Marriott Fishkill
Reception
Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
2.5 star property
Goshen
8.8 out of 10, Excellent, (1001)
Located just 5 minutes from LEGOLAND® New York, this hotel offers a seasonal outdoor pool and 24-hour fitness center. Guests love the free hot breakfast, convenient parking, and helpful staff. Charles J. Everett Memorial and Stewart Airport are nearby for added exploration options.
"Rooms were clean and as expected. Bed was a bit soft for our taste, but acceptable. Breakfast options were routine, scrambled eggs, bacon or sausage on alternating days, oatmeal, waffles, bagel, toast, English muffins... Pleasant and helpful staff, smooth check-in and check-out. Overall a pleasant place."
United States
Joon
The price is ￥15,704
￥19,336 total
includes taxes & fees
Dec 21 - Dec 22
Fairfield Inn & Suites by Marriott Goshen Middletown
Desk, iron/ironing board, free cribs/infant beds, rollaway beds
Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84
2.5 star property
Fishkill
8.8 out of 10, Excellent, (1005)
Conveniently located near a train station, this Fishkill hotel offers complimentary continental breakfast, WiFi, and parking. Work out in the fitness center before exploring nearby Fishkill Golf Course and Fishkill Ridge. Guests praise the clean rooms and helpful staff.
"Great staff, friendly, very clean room!"
United States
Amanda
The price is ￥13,877
￥15,698 total
includes taxes & fees
Dec 19 - Dec 20
Quality Inn & Suites Fishkill South near I-84
Lobby
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1007)
Conveniently located near Woodbury Common Premium Outlets, this welcoming hotel offers a refreshing indoor pool and complimentary breakfast that guests rave about. Rooms include refrigerators and microwaves, plus free WiFi and parking enhance the experience.
"Great stay and room was very nice"
United States
Emmanuel
The price is ￥14,826
￥18,255 total
includes taxes & fees
Dec 21 - Dec 22
Hampton Inn Harriman Woodbury
Free daily English breakfast
Tru by Hilton Middletown

Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (956)
Experience comfort at this Middletown hotel with complimentary English breakfast and WiFi. Just a short drive from LEGOLAND® New York and Orange County Fairgrounds, guests can enjoy the 24-hour fitness center and outdoor terrace after a day of adventures.
"Staff both during check in and out were great . Great stay ."
United States
david
The price is ￥13,932
￥16,455 total
includes taxes & fees
Dec 21 - Dec 22
Tru by Hilton Middletown
Terrace/patio
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
2.5 star property
Fishkill
8.4 out of 10, Very Good, (1001)
Discover this Mid-Hudson Valley haven offering a hot tub, 24-hour fitness center, and complimentary breakfast. Near Van Wyck Homestead Museum and Fishkill Golf Course, enjoy clean rooms with refrigerators and microwaves, plus free WiFi and parking.
"Very nice stay."
United States
Peter
The price is ￥14,795
￥16,737 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
Property amenity
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.6 out of 10, Excellent, (1002)
Located 10 minutes from LEGOLAND® New York, this hotel offers American cuisine at The Bistro restaurant and bar. Enjoy the indoor pool, 24-hour fitness center, free WiFi, and parking while staying near Galleria at Crystal Run.
"The hotel was very clean, enjoyed my stay would recommend "
United States
Jessica
The price is ￥14,429
￥17,044 total
includes taxes & fees
Dec 28 - Dec 29
Courtyard by Marriott Middletown Goshen
Free continental breakfast on weekdays
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.6 out of 10, Excellent, (1002)
Enjoy easy access to LEGOLAND® New York from this welcoming Middletown hotel. Start your day with free breakfast before swimming in the indoor pool. After exploring nearby Paramount Theatre, return to comfortable rooms with complimentary WiFi and parking.
"Love this hotel "
United States
Jennifer
The price is ￥15,621
￥18,453 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Sleep Inn & Suites Middletown - Goshen
Indoor pool
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very Good, (1004)
Located just minutes from Stewart Airport, this welcoming hotel offers a refreshing indoor pool and convenient fitness center. Enjoy free WiFi and parking while exploring nearby Resorts World Hudson Valley and Hamilton Fish Bridge.
"Fast check in, great parking area. "
United States
Helene
The price is ￥16,169
￥18,291 total
includes taxes & fees
Dec 14 - Dec 15
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
View from room
Appalachian Motel

Appalachian Motel

Appalachian Motel
2.0 star property
Vernon
7.6 out of 10, Good, (515)
Set in Vernon, this inviting motel provides easy access to Mountain Creek Waterpark and Ski Resort. Enjoy hiking trails and snowboarding nearby, plus convenient amenities like room service, making it perfect for adventure seekers.
"I would stay here again"
United States
Lyanlex
The price is ￥9,796
￥11,228 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Appalachian Motel
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

The Rock Sports Complex

4.0/5 (10 reviews)
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.
See properties

Goosepond Mountain State Park

4.0/5 (3 reviews)
You can take time to visit Goosepond Mountain State Park during your travels to Chester. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
See properties

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.

See all hotels in Chester
Black dirt region farm Chester New York

Top Chester Hotel Reviews

Hampton Inn Nanuet

Hampton Inn Nanuet

10/10 Excellent
"Friendly and professional staff. Clean rooms, great breakfast. "
Linda 1-night trip
Posted 2 days ago
Hampton Inn Nanuet

More cheap stays in Chester

Super 8 by Wyndham Mahwah

Super 8 by Wyndham Mahwah

160 State Route 17 South Mahwah NJ
The price is ￥11,782 per night from Jan 4 to Jan 5
￥11,782
￥13,504 total
Jan 4 - Jan 5, 2026
includes taxes & fees
7.2/10 Good! (1,000 reviews)

Frequently asked questions

What's the best place to stay in Chester?
The Dominion House Bed & Breakfast is ranked highly by Expedia customers. This B&B offers free breakfast and an outdoor pool. Holiday Inn Express Hotel & Suites Chester by IHG is another top choice for your trip based on traveler reviews. See all available top hotels, or vacation rentals in Chester.
What's the top vacation rental in Chester?
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: Visitors like this Chester vacation home rental. It offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and a coffee maker, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. See all 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.
Where can I learn more about changing or cancelling my trip to Chester?
For more details about updating your trip to Chester or cancelling it, click here.
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.
Where is the best hotel to stay with easy access to The Rock Sports Complex?
Holiday Inn Express Hotel & Suites Chester, an IHG Hotel is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and an indoor pool. It's located just a short 0.8 mi (1.3 km) from The Rock Sports Complex. Other good options within 5 miles include Fairfield Inn & Suites by Marriott Goshen Middletown and NATURE'S NIRVANA FOR FAMILY AND FRIEND.
What about the best place to stay near Castle Fun Center?
One of the top choices for your stay is Holiday Inn Express Hotel & Suites Chester, an IHG Hotel, located a short 0.4 mi (0.6 km) from Castle Fun Center, and this hotel offers free breakfast and an indoor pool. Fairfield Inn & Suites by Marriott Goshen Middletown and Stagecoach Inn are two other good options within a few miles.
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 the best hotel near Stewart International Airport (SWF)?
Howard Johnson by Wyndham Newburgh is a popular hotel, featuring free breakfast and free WiFi. It's located a short 0.8 mi (1.2 km) from Stewart Intl. Airport. Other options within close proximity to the airport include Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport and Super 8 by Wyndham Newburgh/West Point Near Stewart Airport.
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. In Chester, there are 18 hotels and other accommodations to choose from. Find out more about Chester.
What are the top places to visit in Chester?
Favorite places to visit include Castle Fun Center, The Rock Sports Complex, and Goosepond Mountain State Park. Additionally, you might want to add Museum Village to your itinerary. 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.

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