Find hotels in Chester, NY from $76

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May 13 - May 14
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May 14 - May 15
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Compare 973 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Just Renovated ! Mountain Creek -Ski-In-Ski-Out, Pool, Hot Tub, Sauna- Mtn View
Property grounds
Just Renovated ! Mountain Creek -Ski-In-Ski-Out, Pool, Hot Tub, Sauna- Mtn View
10.0 out of 10, Exceptional, (36)
"We’ve stayed at a few condos in the past but Kirk and Melissa’s is my fav! Everything is decorated so beautiful and it was so clean! Having a fridge is always a huge plus! The view from the balcony is lovely! Parking is convenient and it was so quiet! We look forward to staying again! "
The price is $149
$294 total
includes taxes & fees
May 14 - May 15
Just Renovated ! Mountain Creek -Ski-In-Ski-Out, Pool, Hot Tub, Sauna- Mtn View
Rustic Chic at Mountain Creek! Pool, Hot Tub, Sauna, Open ALL Year Round!
Outdoor pool, a heated pool
Rustic Chic at Mountain Creek! Pool, Hot Tub, Sauna, Open ALL Year Round!
10.0 out of 10, Exceptional, (38)
"We were only staying for the one night and we found the whole process between checking in, parking and communicating with Stacey was very easy and welcoming. While the facility itself didn't have a ton of other guest (based on the season I assume), all of the amenities were working away i.e. the heated pool, sauna, hot tub etc. The apartment was cozy and had a lovely welcome package with loads of tips for food and activities nearby which we made use of. Thanks for your quick communication...
The price is $135
$257 total
includes taxes & fees
May 14 - May 15
Rustic Chic at Mountain Creek! Pool, Hot Tub, Sauna, Open ALL Year Round!
Chalet Condo at Mtn Creek Resort- Ski, Snowboard, Hike, Legoland, NYC 1 Hour
Fridge, microwave, oven, stovetop
Chalet Condo at Mtn Creek Resort- Ski, Snowboard, Hike, Legoland, NYC 1 Hour
10.0 out of 10, Exceptional, (24)
"We had to travel to this area for my daughter’s dance competition and this was the perfect fit for what we needed. It’s located directly next to The Minerals Hotel (a part of Crystal Springs). The place was very clean and had nice updates for an older townhome. You cannot use any part of the mountain creek resort or the minerals resort though, that’s the only downside."
The price is $150
$319 total
includes taxes & fees
May 14 - May 15
Chalet Condo at Mtn Creek Resort- Ski, Snowboard, Hike, Legoland, NYC 1 Hour
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The Orange Inn Boutique Hotel
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 $243
$288 total
includes taxes & fees
May 15 - May 16
The Orange Inn Boutique Hotel
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Property grounds
Cozy Loft Cabin high above Bashakill Wildlife Refuge
9.6 out of 10, Exceptional, (9)
"Nice"
The price is $120
$178 total
includes taxes & fees
May 14 - May 15
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Stagecoach Inn
Roosevelt #3, 1 King Bed | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
Stagecoach Inn
3.5 star property
9.6 out of 10, Exceptional, (65)
"This unique property was awesome. The Staff were welcoming and helpful. The room and private bathroom were luxurious and provided a quiet and extravagant comfort without being pretentious. The extra amenities such as makeup washcloths, a glass container with full-size cotton balls and Q-tips were an added perk (after driving through a snow squalls- was much needed)."
The price is $189
$234 total
includes taxes & fees
May 14 - May 15
Stagecoach Inn
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, (927)
"Great service, very clean, great location!"
The price is $104
$117 total
includes taxes & fees
May 14 - May 15
Sleep Inn & Suites Monroe - Woodbury
Residence Inn by Marriott Middletown Goshen
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 $139
$164 total
includes taxes & fees
May 28 - May 29
Residence Inn by Marriott Middletown Goshen
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, (377)
"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 19 - May 20
La Quinta Inn & Suites by Wyndham Middletown
The Dominion House Bed & Breakfast
Exterior
The Dominion House Bed & Breakfast
9.2 out of 10, Wonderful, (218)
"Very accommodating, rooms were comfortable and clean. Breakfast was great. Overall quick but great stay. Will definitely stay again. "
The price is $215
$243 total
includes taxes & fees
May 16 - May 17
The Dominion House Bed & Breakfast
Inn at Stony Creek
Miscellaneous
Inn at Stony Creek
3.0 star property
9.2 out of 10, Wonderful, (442)
"Joe and Bill are amazing owners of the Bed and Breakfast. Very kind and they are easily accessible if you need anything. Great experience!"
The price is $205
$232 total
includes taxes & fees
May 14 - May 15
Inn at Stony Creek
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 $131
$158 total
includes taxes & fees
May 27 - May 28
Home2 Suites by Hilton 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, (1004)
"Will stay again."
The price is $110
$120 total
includes taxes & fees
May 26 - May 27
Hampton Inn Matamoras/Milford
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
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
Sleep Inn & Suites Middletown - Goshen
BBQ/picnic area
Sleep Inn & Suites Middletown - Goshen
2.5 star property
8.6 out of 10, Excellent, (843)
"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
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 $123
$146 total
includes taxes & fees
May 27 - May 28
Hampton Inn by Hilton Middletown
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 $76
$85 total
includes taxes & fees
May 20 - May 21
Sussex Motel
Tru by Hilton Middletown
Reception
Tru by Hilton Middletown
2.5 star property
8.2 out of 10, Very Good, (682)
"Staff at the desk was great "
The price is $114
$135 total
includes taxes & fees
May 21 - May 22
Tru by Hilton Middletown
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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.