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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
2.5 star property
Chester
8.6 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Modern hotel near LEGOLAND® New York with indoor pool and complimentary perks.
"timely & courteous check-in; clean rooms; quiet environment; perfect location for our needs "
United States
Orlando
The price is ￥14,242
￥16,824 total
includes taxes & fees
Feb 1 - Feb 2
Holiday Inn Express Hotel & Suites Chester by IHG
Exterior

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233 reviews)
  • cleanliness
    Charming bed and breakfast near LEGOLAND® New York and premium shopping outlets.
"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 ￥32,796
￥37,101 total
includes taxes & fees
Feb 16 - Feb 17
The Dominion House Bed & Breakfast
Lobby

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
10.0 out of 10, Exceptional, (4 reviews)
"Close to town, restaurants, gas, etc… Very clean, comfy bed, decent breakfast"
United States
Michael
The price is ￥14,188
￥17,470 total
includes taxes & fees
Mar 1 - Mar 2
Comfort Suites Central Valley - Woodbury
Lobby

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Quiet retreat near LEGOLAND with seasonal pool and complimentary amenities.
"Staff, Room Clean, Early breakfast. "
United States
Jessica
The price is ￥12,318
￥14,551 total
includes taxes & fees
Feb 19 - Feb 20
Hampton Inn by Hilton Middletown
Free daily continental breakfast

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
7.4 out of 10, Good, (22 reviews)
"Nice clean rooms. Updated by Hilton. Well priced, good value "
United States
Lewis
The price is ￥13,337
￥15,421 total
includes taxes & fees
Feb 7 - Feb 8
Spark by Hilton Fishkill
Exterior

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, (819 reviews)
  • cleanliness
    Unwind near City Winery in Montgomery with a complimentary hot breakfast.
"The staff was great! The room was clean and the breakfast was excellent."
Canada
Joey
The price is ￥12,508
￥14,149 total
includes taxes & fees
Feb 1 - Feb 2
Holiday Inn Express & Suites Montgomery by IHG
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
2.5 star property
Fishkill
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Enjoy a complimentary breakfast and fitness center at this Fishkill train station hotel.
"Good low-cost hotel with decent continental breakfast."
United States
Nancy
The price is ￥13,614
￥15,742 total
includes taxes & fees
Feb 7 - Feb 8
Quality Inn & Suites Fishkill South near I-84
Room, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,022 reviews)
  • cleanliness
    Convenient lodging near Woodbury Common Outlets with free breakfast and parking.
"Room always comfortable and convenient location "
United States
laura
The price is ￥12,188
￥13,787 total
includes taxes & fees
Feb 26 - Feb 27
Sleep Inn & Suites Monroe - Woodbury
Free daily English breakfast

Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (969 reviews)
  • cleanliness
    Modern hotel near LEGOLAND® offering free breakfast and convenient parking.
"Yes I enjoyed my stay"
United States
Vivette
The price is ￥13,634
￥16,105 total
includes taxes & fees
Feb 5 - Feb 6
Tru 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
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1,061 reviews)
  • cleanliness
    Lakeside retreat next to golf course offering quiet relaxation and convenient amenities.
"Clean room, helpful staff and good bar/restaurant "
United States
Stephen
The price is ￥15,510
￥18,052 total
includes taxes & fees
Feb 22 - Feb 23
DoubleTree by Hilton Hotel Nanuet
Restaurant

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1,000 reviews)
  • cleanliness
    Rejuvenating mountain escape with spa services and seasonal outdoor pool.
"The stone lodges are cute and cozy and the staff were quick and helpful if you needed anything. Great for a short stay at a reasonable price."
United States
Judith
The price is ￥14,522
￥16,428 total
includes taxes & fees
Feb 18 - Feb 19
Overlook Lodge at Bear Mountain
Reception

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, (1,001 reviews)
  • cleanliness
    Experience comfort near LEGOLAND with a complimentary hot breakfast.
"Was nice place to stay I like it "
United States
Artemio
The price is ￥14,186
￥17,465 total
includes taxes & fees
Feb 15 - Feb 16
Fairfield Inn & Suites by Marriott Goshen Middletown
Lobby

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.2 out of 10, Wonderful, (999 reviews)
  • cleanliness
    Serene getaway near Interstate 84, offering complimentary breakfast and indoor pool.
"Yes stay was pleasant "
United States
henry
The price is ￥14,262
￥16,135 total
includes taxes & fees
Feb 7 - Feb 8
Comfort Suites Fishkill near Interstate 84
Exterior

Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet
2.5 star property
Nanuet
8.4 out of 10, Very Good, (1,055 reviews)
  • cleanliness
    Experience comfort at this Nanuet hotel near train station and The Shops at Nanuet.
"Staff was nice, bed comfortable. "
United States
Misty
The price is ￥11,969
￥13,929 total
includes taxes & fees
Feb 2 - Feb 3
Sonesta Simply Suites Nanuet
Lobby

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,048 reviews)
  • cleanliness
    Minutes from premium outlets with a pool, fitness center, and free breakfast.
"Easy check in, clean room, very good breakfast."
United States
Robert
The price is ￥16,136
￥19,869 total
includes taxes & fees
Feb 4 - Feb 5
Hampton Inn Harriman Woodbury
Terrace/patio

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, (1,002 reviews)
  • cleanliness
    Relax in scenic Fishkill with an indoor pool and modern comforts.
"Great customer service and breakfast was excellent "
United States
Dennis
The price is ￥14,242
￥16,466 total
includes taxes & fees
Jan 30 - Jan 31
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
Lobby

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (996 reviews)
  • cleanliness
    Serene ski retreat near Mountain Creek with peaceful setting and outdoor access.
"Good breakfast, and everything was clean in a great room. "
United States
Steven
The price is ￥12,946
￥14,840 total
includes taxes & fees
Mar 1 - Mar 2
Quality Inn near Mountain Creek
Exterior

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, (966 reviews)
  • cleanliness
    Near LEGOLAND and convenient for families, this hotel promises a relaxing stay.
"GREAT STAY, CLEAN HOTEL AND ROOM, GREAT POOL AND HOT TUB GYM IS CLEAN LOVED IT"
United States
NICOLE
The price is ￥15,818
￥18,684 total
includes taxes & fees
Feb 22 - Feb 23
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Indoor pool

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, (1,017 reviews)
  • cleanliness
    Unwind near Stewart Airport with a complimentary shuttle and indoor pool.
"Superb place to stay."
United States
Denessy
The price is ￥14,700
￥16,629 total
includes taxes & fees
Feb 1 - Feb 2
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
View from property

Inn on the Hudson

Inn on the Hudson
2.0 star property
Peekskill
7.0 out of 10, Good, (1,000 reviews)
  • cleanliness
    Experience the Hudson River views at this Peekskill gem with free breakfast.
"The staff was really welcoming!"
United States
Devis
The price is ￥13,576
￥15,527 total
includes taxes & fees
Feb 15 - Feb 16
Inn on the Hudson
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)
This dedicated sports venue hosts baseball and softball tournaments on well-maintained turf fields. Bring portable chairs and sun protection to enjoy the games in comfort at this local athletic hub.
See properties

Goosepond Mountain State Park

4.0/5 (3 reviews)
This 1,558-acre undeveloped park offers a tranquil escape with diverse trails through woods, fields, and wetlands. Bring binoculars to spot songbirds from the boardwalk that crosses marshy areas.
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 Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"Room is clean and spacious. Staff are extremely friendly and helpful. Breakfast is good."
Yeng ping 2-night trip
Posted 3 days ago
Hampton Inn Harriman Woodbury

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 ￥11,585 per night from Feb 1 to Feb 2
￥11,585
￥13,279 total
Feb 1 - Feb 2
includes taxes & fees
7.2/10 Good! (1,000 reviews)

Frequently asked questions

What's the best place to stay in Chester?
Based on our traveler 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 options for your trip to the area are DoubleTree by Hilton Hotel Nanuet and Crowne Plaza Suffern - Mahwah by IHG. 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 an electric kettle, 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 19 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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