Find hotels in Chester, NY from ￥11,684

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May 14 - May 15
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May 15 - May 16
This weekend
May 17 - May 19
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May 24 - May 26

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Compare 973 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Lobby
Microtel Inn & Suites by Wyndham Middletown
2.0 star property
7.2 out of 10, Good, (999)
"The staff were amazing. From the gentleman that checked me in to the gentleman that checked me out, the staff were welcoming and accommodating. I ended up checking out a day earlier than planned, and had no issues with being refunded for my unused night. Everyone was happy to answer any questions that I had. The room was small, but clean and the AC worked perfectly. The coffee maker was missing a piece, but that ended up being fine as I ended up not using it. I think I'll ask to have a room that...
The price is ￥15,803
per night
May 19 - May 20
Microtel Inn & Suites by Wyndham Middletown
Room, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board
Sleep Inn & Suites Monroe - Woodbury
2.5 star property
9.4 out of 10, Exceptional, (927)
"Quiet place to stay for one night. "
The price is ￥16,169
per night
May 16 - May 17
Sleep Inn & Suites Monroe - Woodbury
Exterior
Super 8 by Wyndham Middletown
2.5 star property
6.4 out of 10, (1000)
"Close to shopping outlets and quiet"
The price is ￥13,811
per night
May 29 - May 30
Super 8 by Wyndham Middletown
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Reception
Tru by Hilton Middletown
2.5 star property
8.2 out of 10, Very Good, (684)
"Staff at the desk was great "
The price is ￥17,795
per night
May 21 - May 22
Tru by Hilton Middletown
Exterior
Fairfield Inn & Suites by Marriott Goshen Middletown
2.5 star property
8.6 out of 10, Excellent, (857)
"Service was excellent"
The price is ￥17,185
per night
May 27 - May 28
Fairfield Inn & Suites by Marriott Goshen Middletown
Exterior
La Quinta Inn & Suites by Wyndham Middletown
2.5 star property
9.2 out of 10, Wonderful, (379)
"Our stay was for 2 days we chose that hotel because it was pet friendly the rooms were ok I stayed in nicer hotels. The continental breakfast was average the sausages looked boiled etc not pleasant seen better"
The price is ￥19,730
per night
May 19 - May 20
La Quinta Inn & Suites by Wyndham Middletown
Property entrance
Mountain Creek
3.0 star property
8.0 out of 10, Very Good, (480)
"The views are beautiful and the lobby so pretty! Our room could have been nicer the carpet was coming up in areas and was covered by a floor mat. Love the area not a bad stay. "
The price is ￥58,430
per night
Jun 2 - Jun 3
Mountain Creek
Lobby
Courtyard by Marriott Middletown Goshen
3.0 star property
8.6 out of 10, Excellent, (714)
"Staff was very friendly and accommodating. Rooms were clean and spacious. Close to everything."
The price is ￥18,423
per night
May 19 - May 20
Courtyard by Marriott Middletown Goshen
Indoor pool, sun loungers
Best Western Hunt's Landing Hotel Matamoras/Milford
3.0 star property
8.2 out of 10, Very Good, (1000)
"Loved the stay and the process to check in and check out was easy. Just weird that it smelled like weed on the floor when walking to and from my room"
The price is ￥16,865
per night
May 20 - May 21
Best Western Hunt's Landing Hotel Matamoras/Milford
BBQ/picnic area
Sleep Inn & Suites Middletown - Goshen
2.5 star property
8.6 out of 10, Excellent, (844)
"The location is perfect and near family when we are visiting. I appreciate the breakfast options as well."
The price is ￥20,240
per night
May 15 - May 16
Sleep Inn & Suites Middletown - Goshen
Seasonal outdoor pool
Days Inn by Wyndham Middletown
2.0 star property
6.6 out of 10, (553)
"Wish they had smoking rooms.I’m a big 420 supporter so I’m back and forth outside to smoke"
The price is ￥16,552
per night
May 28 - May 29
Days Inn by Wyndham Middletown
Pillowtop beds, in-room safe, individually decorated
Holiday Inn Express & Suites Middletown - Goshen, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (538)
"The property is close to a gas station for easy snacks and necessities."
The price is ￥19,146
per night
May 19 - May 20
Holiday Inn Express & Suites Middletown - Goshen, an IHG Hotel
Lobby
Hampton Inn Matamoras/Milford
2.5 star property
8.8 out of 10, Excellent, (1001)
"Will stay again."
The price is ￥17,235
per night
May 26 - May 27
Hampton Inn Matamoras/Milford
Courtyard
Home2 Suites by Hilton Middletown
3.0 star property
9.0 out of 10, Wonderful, (571)
"Great day would absolutely do it again right in the middle of everything you have Walmart and all your other places that you need to go right there by your hotel"
The price is ￥20,392
per night
May 28 - May 29
Home2 Suites by Hilton Middletown
Lobby
Quality Inn near Mountain Creek
2.5 star property
7.6 out of 10, Good, (790)
"It was exactly what we were looking for and will use this property again."
The price is ￥12,514
per night
May 15 - May 16
Quality Inn near Mountain Creek
Exterior
Hampton Inn by Hilton Middletown
2.5 star property
8.6 out of 10, Excellent, (865)
"I was there for a training, it was very nice to study."
The price is ￥19,211
per night
May 21 - May 22
Hampton Inn by Hilton Middletown
Exterior
Appalachian Motel
2.0 star property
7.6 out of 10, Good, (393)
"Beautiful setting. Scary (dangerous) access to driveway off and onto fast curving hillside road. Would benefit from convex traffic mirror opposite driveway. Beds extremely comfortable. Shower good. Everything else adequate, but that's okay with us. Had all we needed."
The price is ￥11,684
per night
May 15 - May 16
Appalachian Motel
Exterior
The Orange Inn Boutique Hotel
2.0 star property
9.8 out of 10, Exceptional, (68)
"The restaurant was second to none! Fantastic service, knowledgeable waiters and waitresses and the Menu was stacked, unique and Delicious. What a great experience!"
The price is ￥35,544
per night
May 16 - May 17
The Orange Inn Boutique Hotel
Exterior
Residence Inn by Marriott Middletown Goshen
3.0 star property
9.4 out of 10, Exceptional, (223)
"Great place to stay . I’ll be back soon ! "
The price is ￥23,278
per night
Jun 4 - Jun 5
Residence Inn by Marriott Middletown Goshen
Comfort Room, 2 Double Beds, Non Smoking, Refrigerator & Microwave | Free WiFi, bed sheets
Sussex Motel
2.5 star property
8.6 out of 10, Excellent, (170)
"Very nice owner , great customer service "
The price is ￥11,839
per night
May 28 - May 29
Sussex Motel
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See all available properties in Chester
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.

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, an IHG Hotel 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?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: You might want to consider this vacation rental near Chester, which is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. It offers a garden, a selection of games, and a spa tub so you can immerse yourself in your vacation. 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's the best accommodation for a budget-friendly stay in Chester?

Based on reviews, Holiday Inn Express Hotel & Suites Chester, an IHG Hotel is a popular 2.5-star hotel for our travelers looking for an economical choice, and features free breakfast and free WiFi. View all budget hotels in Chester.

What's the best hotel for a couple visiting Chester?

The Dominion House Bed & Breakfast is a favorite 3.5-star B&B for couples, and features wedding services and free breakfast. See all romantic hotels in Chester.

What is the favorite LGBTQ-friendly place to stay in Chester?

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel 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's the best place to stay for a winter vacation in Chester?

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel is a top hotel for hitting the ski slopes, and features free breakfast and free WiFi. This hotel is located 21 minutes by car from Mount Peter Ski Area. See all ski hotels in Chester.

What are some accommodations with pools in Chester?

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel 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 spa hotel in Chester?

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel is a highly recommended spa hotel with a pool. See all spa hotels 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 20 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.