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26 Aug - 27 Aug
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27 Aug - 28 Aug
This weekend
29 Aug - 31 Aug
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5 Sept - 7 Sept

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Top 10 trending Chester hotels

Appalachian Motel
Free self-parking

Appalachian Motel

2.0 star property
7.6 out of 10, Good, (495)
"This is a privately owned hotel the manager didn't bother you It was a quiet place very clean however be careful turning into the driveway it's a very sharp turn but overall it was a great stay and a great value"
The price is €66
includes taxes & fees
3 Sept - 4 Sept
Appalachian Motel
Hampton Inn Harriman Woodbury
Lobby

Hampton Inn Harriman Woodbury

2.5 star property
9.2 out of 10, Wonderful, (1012)
"Great stay great staff great accommodations "
The price is €116
includes taxes & fees
2 Sept - 3 Sept
Hampton Inn Harriman Woodbury
Fairfield Inn & Suites by Marriott Goshen Middletown
View from property

Fairfield Inn & Suites by Marriott Goshen Middletown

2.5 star property
8.8 out of 10, Excellent, (1003)
"Great place to stay when you’re in need of relaxation and some family time!"
The price is €107
includes taxes & fees
23 Sept - 24 Sept
Fairfield Inn & Suites by Marriott Goshen Middletown
Holiday Inn Express Hotel & Suites Chester by IHG
Exterior

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 star property
8.4 out of 10, Very good, (1006)
"Great staff and rooms "
The price is €109
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express Hotel & Suites Chester by IHG
The Dominion House Bed & Breakfast
Superior Double Room, Ensuite (Primrose) | Miscellaneous

The Dominion House Bed & Breakfast

2.0 star property
9.2 out of 10, Wonderful, (227)
"Amazing hospitality,"
The price is €209
includes taxes & fees
9 Sept - 10 Sept
The Dominion House Bed & Breakfast
Sleep Inn & Suites Monroe - Woodbury
Room, 1 King Bed, Non Smoking

Sleep Inn & Suites Monroe - Woodbury

2.5 star property
9.4 out of 10, Exceptional, (1006)
"great place to stay"
The price is €109
includes taxes & fees
2 Sept - 3 Sept
Sleep Inn & Suites Monroe - Woodbury
High Point Motel
Front of property

High Point Motel

2.0 star property
8.8 out of 10, Excellent, (62)
"Peaceful and a nice views staff was very friendly and nice definitely will return"
The price is €84
includes taxes & fees
7 Sept - 8 Sept
High Point Motel
Countryside Motel
Apartment, 2 Double Beds (Ground Floor) | Living area

Countryside Motel

2.0 star property
7.2 out of 10, Good, (245)
"Reasonably priced "
The price is €79
includes taxes & fees
28 Aug - 29 Aug
Countryside Motel
Sleep Inn & Suites Middletown - Goshen
BBQ/picnic Area

Sleep Inn & Suites Middletown - Goshen

2.5 star property
8.4 out of 10, Very good, (1015)
"Great stay"
The price is €104
includes taxes & fees
23 Sept - 24 Sept
Sleep Inn & Suites Middletown - Goshen
Quality Inn & Suites Fishkill South near I-84
Desk, iron/ironing board, free cots/infant beds, rollaway beds

Quality Inn & Suites Fishkill South near I-84

2.5 star property
8.8 out of 10, Excellent, (1016)
"Good place to stay"
The price is €93
includes taxes & fees
7 Sept - 8 Sept
Quality Inn & Suites Fishkill South near I-84
Overlook Lodge at Bear Mountain
Restaurant

Overlook Lodge at Bear Mountain

2.5 star property
8.4 out of 10, Very good, (1011)
"3rd stay at this cottage and we love it. Will definitely be staying here in the future "
The price is €164
includes taxes & fees
28 Aug - 29 Aug
Overlook Lodge at Bear Mountain
The Hamlet Inn at Warwick
Deluxe Double Room

The Hamlet Inn at Warwick

2.5 star property
7.4 out of 10, Good, (123)
"Great price rooms clean"
The price is €92
includes taxes & fees
2 Sept - 3 Sept
The Hamlet Inn at Warwick
Hampton Inn by Hilton Middletown
Exterior

Hampton Inn by Hilton Middletown

2.5 star property
8.6 out of 10, Excellent, (1003)
"Property was clean and staff was friendly. "
The price is €103
includes taxes & fees
2 Sept - 3 Sept
Hampton Inn by Hilton Middletown
Sussex Motel
Comfort Room, 2 Double Beds, Non Smoking, Refrigerator & Microwave

Sussex Motel

2.5 star property
8.6 out of 10, Excellent, (340)
"It was a sweet stay in this motel, the host was very helpful and welcoming. "
The price is €80
includes taxes & fees
14 Sept - 15 Sept
Sussex Motel
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Indoor pool

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2.0 star property
8.4 out of 10, Very good, (1009)
"Excellent hotel!!"
The price is €112
includes taxes & fees
1 Sept - 2 Sept
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Rolling Hills Motel
Property grounds

Rolling Hills Motel

2.0 star property
8.4 out of 10, Very good, (171)
"Great stay"
The price is €80
includes taxes & fees
7 Sept - 8 Sept
Rolling Hills Motel
Quality Inn near Mountain Creek
Lobby

Quality Inn near Mountain Creek

2.5 star property
7.6 out of 10, Good, (933)
"Would definitely stay here again"
The price is €91
includes taxes & fees
11 Sept - 12 Sept
Quality Inn near Mountain Creek
Comfort Suites Fishkill near Interstate 84
Free daily buffet breakfast

Comfort Suites Fishkill near Interstate 84

2.5 star property
9.0 out of 10, Wonderful, (1004)
"The staff was friendly and efficient. The room was clean and the bed comfortable. It was a great central location to explore the Hudson Valley attractions!"
The price is €109
includes taxes & fees
14 Sept - 15 Sept
Comfort Suites Fishkill near Interstate 84
LEGOLAND Hotel NEW York
Outdoor pool

LEGOLAND Hotel NEW York

3.0 star property
7.0 out of 10, Good, (2)
The price is €245
includes taxes & fees
1 Sept - 2 Sept
LEGOLAND Hotel NEW York
Cadet Motel
Exterior

Cadet Motel

2.0 star property
6.4 out of 10, (292)
"It was a great little motel for a 2 day business trip. Affordable, clean, and safe. "
The price is €80
includes taxes & fees
2 Sept - 3 Sept
Cadet Motel
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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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 Centre for go-karts, mini-golf, and arcade games.

See all hotels in Chester

Top Chester Hotel Reviews

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"Great "
MARIANA 1-night trip
Posted 2 days ago
Hampton Inn Harriman Woodbury

More cheap stays in Chester

More cheap stays in Chester

Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

20 Overlook Blvd, Nanuet, NY
The price is €111 per night from 1 Sept to 2 Sept
€111
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 by IHG is another top choice for your trip based on traveller reviews. See all available top hotels, or vacation rentals in Chester.

What are some of the best holiday rentals that Chester has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Chester 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 that 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 that most room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

What is the favourite LGBTQ-friendly accommodation in Chester?

Holiday Inn Express Hotel & Suites Chester by IHG is a top LGBTQ-friendly hotel that features free breakfast and free Wi-Fi. The Dominion House Bed & Breakfast is another good option for your trip. See all available hotels listed as LGBTQ-friendly in Chester.

What are some accommodation options 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 staying in Chester like?

Visitors to Chester will definitely enjoy the shopping and restaurants. Tourists can also enjoy the city's ski areas and coffee shops. Top sights around the area include LEGOLAND® New York and Woodbury Common Premium Outlets. In Chester, there are 18 hotels and other accommodation options to choose from. Find out more about Chester.

What are the top places to visit in Chester?

Favourite 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. Take a look at what more there is 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 temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Chester are January, February, March and April, with each month seeing an average of 16 cm of snowfall.