Find hotels in Chester, NY from $74

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Check Chester hotel prices

Tonight
May 11 - May 12
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May 12 - May 13
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May 17 - May 19

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

Microtel Inn & Suites by Wyndham Middletown
Lobby
Microtel Inn & Suites by Wyndham Middletown
2.0 star property
7.2 out of 10, Good, (1001)
"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 $110
$130 total
includes taxes & fees
May 16 - May 17
Microtel Inn & Suites by Wyndham Middletown
Sleep Inn & Suites Monroe - Woodbury
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, (926)
"Nice hotel next to woodbury common premium outlets. It is literally in the woods in a beautiful location. Very friendly staff. Comfortable and large rooms and good breakfast. Comfortable parking for the car."
The price is $104
$117 total
includes taxes & fees
May 12 - May 13
Sleep Inn & Suites Monroe - Woodbury
Super 8 by Wyndham Middletown
Room, 1 King Bed, Accessible, Bathtub | In-room safe, desk, laptop workspace, blackout drapes
Super 8 by Wyndham Middletown
2.5 star property
6.4 out of 10, (1001)
"Close to shopping outlets and quiet"
The price is $88
$104 total
includes taxes & fees
May 29 - May 30
Super 8 by Wyndham Middletown
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Tru by Hilton Middletown
Reception
Tru by Hilton Middletown
2.5 star property
8.2 out of 10, Very Good, (677)
"It was very clean. The check-in process was quick and easy. The lady who check us in was professional and kind."
The price is $112
$133 total
includes taxes & fees
May 20 - May 21
Tru by Hilton Middletown
Fairfield Inn & Suites by Marriott Goshen 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 $110
$155 total
includes taxes & fees
May 27 - May 28
Fairfield Inn & Suites by Marriott Goshen Middletown
La Quinta Inn & Suites by Wyndham Middletown
Exterior
La Quinta Inn & Suites by Wyndham Middletown
2.5 star property
9.2 out of 10, Wonderful, (375)
"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 $127
$150 total
includes taxes & fees
May 16 - May 17
La Quinta Inn & Suites by Wyndham Middletown
Mountain Creek
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 $374
$448 total
includes taxes & fees
Jun 2 - Jun 3
Mountain Creek
Courtyard by Marriott Middletown Goshen
Property amenity
Courtyard by Marriott Middletown Goshen
3.0 star property
8.6 out of 10, Excellent, (713)
"Staff was very friendly and accommodating. Rooms were clean and spacious. Close to everything."
The price is $114
$134 total
includes taxes & fees
May 27 - May 28
Courtyard by Marriott Middletown Goshen
Best Western Hunt's Landing Hotel Matamoras/Milford
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 $104
$113 total
includes taxes & fees
May 19 - May 20
Best Western Hunt's Landing Hotel Matamoras/Milford
Sleep Inn & Suites Middletown - Goshen
BBQ/picnic area
Sleep Inn & Suites Middletown - Goshen
2.5 star property
8.6 out of 10, Excellent, (842)
"The location is perfect and near family when we are visiting. I appreciate the breakfast options as well."
The price is $126
$142 total
includes taxes & fees
May 28 - May 29
Sleep Inn & Suites Middletown - Goshen
Days Inn by Wyndham Middletown
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 $106
$120 total
includes taxes & fees
May 19 - May 20
Days Inn by Wyndham Middletown
Holiday Inn Express & Suites Middletown - Goshen, an IHG Hotel
Property amenity
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 $123
$145 total
includes taxes & fees
May 19 - May 20
Holiday Inn Express & Suites Middletown - Goshen, an IHG Hotel
Hampton Inn Matamoras/Milford
Lobby
Hampton Inn Matamoras/Milford
2.5 star property
8.8 out of 10, Excellent, (1003)
"Will stay again."
The price is $110
$120 total
includes taxes & fees
May 19 - May 20
Hampton Inn Matamoras/Milford
Home2 Suites by Hilton Middletown
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 $130
$157 total
includes taxes & fees
May 19 - May 20
Home2 Suites by Hilton Middletown
Quality Inn near Mountain Creek
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 $80
$92 total
includes taxes & fees
May 12 - May 13
Quality Inn near Mountain Creek
Hampton Inn by Hilton Middletown
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 $118
$140 total
includes taxes & fees
May 20 - May 21
Hampton Inn by Hilton Middletown
Appalachian Motel
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 $75
$86 total
includes taxes & fees
May 12 - May 13
Appalachian Motel
The Orange Inn Boutique Hotel
Exterior
The Orange Inn Boutique Hotel
2.0 star property
9.8 out of 10, Exceptional, (66)
"We stayed here for 3 nights while in the area visiting friends in the lower valley. This hotel is very nice for the price, convenient location to a lot of sights in the area, comfortable bed and towels. The staff was very nice and helpful in all of our interactions. The bathroom was well lit, has a fan when the light is on, GIANT shower with a rain head. There is a Kurig in the room and two small bottles of water for the coffee machine. The fridge is a wine fridge but fits other things easily....
The price is $250
$295 total
includes taxes & fees
May 15 - May 16
The Orange Inn Boutique Hotel
Residence Inn by Marriott Middletown Goshen
Exterior
Residence Inn by Marriott Middletown Goshen
3.0 star property
9.4 out of 10, Exceptional, (222)
"Great place to stay . I’ll be back soon ! "
The price is $139
$164 total
includes taxes & fees
May 27 - May 28
Residence Inn by Marriott Middletown Goshen
Sussex Motel
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 $74
$83 total
includes taxes & fees
May 12 - May 13
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.