Find hotels in Chester, NY from SAR 319

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Compare 981 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 star property
8.6 out of 10, Excellent, (1001)
"The service at check-in was great. "
The price is SAR 435
SAR 492 total
includes taxes & fees
8 May - 9 May
Holiday Inn Express Hotel & Suites Chester by IHG

The Dominion House Bed & Breakfast

2.0 star property
9.2 out of 10, Wonderful, (224)
"The house and accommodations are beautifully appointed, the hosts were helpful and engaging and the breakfasts were outstanding - make sure you request Susie’s fabulous scones! "
The price is SAR 806
SAR 912 total
includes taxes & fees
7 May - 8 May
The Dominion House Bed & Breakfast

Stagecoach Inn

3.5 star property
9.6 out of 10, Exceptional, (76)
"Unique and quaint inn with lots to offer or do nothing at all except relax!"
The price is SAR 1,031
SAR 1,270 total
includes taxes & fees
7 May - 8 May
Stagecoach Inn

The Orange Inn Boutique Hotel

2.0 star property
9.6 out of 10, Exceptional, (135)
"Loved the shower"
The price is SAR 615
SAR 757 total
includes taxes & fees
6 May - 7 May
The Orange Inn Boutique Hotel

Sleep Inn & Suites Monroe - Woodbury

2.5 star property
9.4 out of 10, Exceptional, (1007)
"We enjoyed our stay there"
The price is SAR 422
SAR 477 total
includes taxes & fees
7 May - 8 May
Sleep Inn & Suites Monroe - Woodbury

Fairfield Inn & Suites by Marriott Goshen Middletown

2.5 star property
8.8 out of 10, Excellent, (941)
"Great place quiet clean nice breakfast staff was great"
The price is SAR 394
SAR 485 total
includes taxes & fees
26 May - 27 May
Fairfield Inn & Suites by Marriott Goshen Middletown

Microtel Inn & Suites by Wyndham Middletown

2.0 star property
7.2 out of 10, Good, (1000)
"Convenient location off highway and near Legoland. It’s set near walkable restaurants too. "
The price is SAR 411
SAR 486 total
includes taxes & fees
12 May - 13 May
Microtel Inn & Suites by Wyndham Middletown

Hampton Inn by Hilton Middletown

2.5 star property
8.6 out of 10, Excellent, (1001)
"Our family needed a quick overnight place and this was perfect! Hampton Inns are our family’s favorite!"
The price is SAR 418
SAR 493 total
includes taxes & fees
26 May - 27 May
Hampton Inn by Hilton Middletown

Courtyard by Marriott Middletown Goshen

3.0 star property
8.6 out of 10, Excellent, (881)
"Staff was super nice and accommodating "
The price is SAR 411
SAR 486 total
includes taxes & fees
26 May - 27 May
Courtyard by Marriott Middletown Goshen

Holiday Inn Express & Suites Middletown - Goshen by IHG

2.5 star property
8.8 out of 10, Excellent, (657)
"Nice place to stay."
The price is SAR 602
SAR 711 total
includes taxes & fees
11 May - 12 May
Holiday Inn Express & Suites Middletown - Goshen by IHG

Days Inn by Wyndham Middletown

2.0 star property
6.4 out of 10, (616)
"Checking in was super smooth. Staff were polite and helpful."
The price is SAR 354
SAR 418 total
includes taxes & fees
8 May - 9 May
Days Inn by Wyndham Middletown

Hampton Inn Harriman Woodbury

2.5 star property
9.2 out of 10, Wonderful, (1011)
"We enjoyed our room very nice and clean the area has a lot to see. "
The price is SAR 504
SAR 621 total
includes taxes & fees
3 Jun - 4 Jun
Hampton Inn Harriman Woodbury

Americas Best Value Inn at Central Valley-Woodbury

2.0 star property
7.0 out of 10, Good, (1004)
"Great location and very quiet. "
The price is SAR 351
SAR 432 total
includes taxes & fees
13 May - 14 May
Americas Best Value Inn at Central Valley-Woodbury

Home2 Suites by Hilton Middletown

3.0 star property
9.0 out of 10, Wonderful, (674)
"Love it...cant wait to come back"
The price is SAR 539
SAR 650 total
includes taxes & fees
26 May - 27 May
Home2 Suites by Hilton Middletown

Super 8 by Wyndham Middletown

2.5 star property
6.2 out of 10, (1004)
"Well situated for our needs"
The price is SAR 319
SAR 377 total
includes taxes & fees
12 May - 13 May
Super 8 by Wyndham Middletown

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3.0 star property
9.2 out of 10, Wonderful, (686)
"Hotel staff was very friendly. Breakfast was excellent and there is a starbucks across the parking lot. Hotel looks brand new inside and out. Will stay there again. "
The price is SAR 475
SAR 561 total
includes taxes & fees
11 May - 12 May
La Quinta Inn & Suites by Wyndham Middletown-Goshen

The Hamlet Inn at Warwick

2.5 star property
7.4 out of 10, Good, (96)
"Most disgusting motel I’ve ever seen "
The price is SAR 356
SAR 403 total
includes taxes & fees
6 May - 7 May
The Hamlet Inn at Warwick

Residence Inn by Marriott Middletown Goshen

3.0 star property
9.4 out of 10, Exceptional, (291)
"Great stay"
The price is SAR 709
SAR 837 total
includes taxes & fees
11 May - 12 May
Residence Inn by Marriott Middletown Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 star property
8.6 out of 10, Excellent, (1003)
"The rooms were really clean and the staff was friendly "
The price is SAR 421
SAR 498 total
includes taxes & fees
26 May - 27 May
Sleep Inn & Suites Middletown - Goshen

Villa Verde BB Greenwood Lake NY

4.0 star property
10.0 out of 10, Exceptional, (2)
"Truly wonderful host and property. Incredible location and impeccable residence- our experience was amazing in every way. We felt incredibly accommodated while also enjoying all the privacy needed within our beautiful suite. My partner was celebrating her 30th birthday- our host went above and beyond to make the trip truly special. She even accommodated her vegan dietary requests for breakfast! Speaking of- the breakfast was incredible- one of the best breakfast experiences I've ever enjoyed....
The price is SAR 761
SAR 936 total
includes taxes & fees
19 May - 20 May
Villa Verde BB Greenwood Lake NY
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.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in

Learn more about Chester

Escape to relaxing Chester! Enjoy its food and skiing.

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 Overlook Lodge at Bear Mountain and La Quinta Inn & Suites by Wyndham Middletown-Goshen. 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.

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. Top sights around the area include LEGOLAND® New York and Woodbury Common Premium Outlets. In Chester, there are 13 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 Museum Village. Additionally, you'll find LEGOLAND® New York and Woodbury Common Premium Outlets in the area. 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.