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Top hotels and accommodation in Chester

Sleep Inn & Suites Monroe - Woodbury
Relax in comfort with a large bed, flat-screen TV, and ample natural light.

Sleep Inn & Suites Monroe - Woodbury

2.5 star property
9.4 out of 10, Exceptional, (1013)
"Staff was friendly, room was very nice and clean, beds were very comfortable "
The price is NZ$211
includes taxes & fees
10 Aug - 11 Aug
Sleep Inn & Suites Monroe - Woodbury
Sleep Inn & Suites Middletown - Goshen
Relax in a serene outdoor space with a round table, benches, and a decorative lamp.

Sleep Inn & Suites Middletown - Goshen

2.5 star property
8.6 out of 10, Excellent, (1020)
"Very nice hotel ! "
The price is NZ$206
includes taxes & fees
10 Aug - 11 Aug
Sleep Inn & Suites Middletown - Goshen
Fairfield Inn & Suites by Marriott Goshen Middletown
Welcome to the Fairfield Inn & Suites, featuring a covered entrance and ample parking.

Fairfield Inn & Suites by Marriott Goshen Middletown

2.5 star property
8.8 out of 10, Excellent, (974)
"Great breakfast, great room. "
The price is NZ$224
includes taxes & fees
7 Aug - 8 Aug
Fairfield Inn & Suites by Marriott Goshen Middletown
Holiday Inn Express Hotel & Suites Chester by IHG
Experience the sleek design of this hotel, featuring a flat roof and a mix of brick and stucco exterior.

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 star property
8.6 out of 10, Excellent, (1014)
"The room was huge; the staff was nice. Breakfast could have a little more options. I would recommend this hotel "
The price is NZ$239
includes taxes & fees
27 July - 28 July
Holiday Inn Express Hotel & Suites Chester by IHG
The Dominion House Bed & Breakfast
Stroll through the serene garden, surrounded by lush plants and a soothing fountain, with a charming gazebo in the distance.

The Dominion House Bed & Breakfast

2.0 star property
9.2 out of 10, Wonderful, (226)
"Amazing hospitality,"
The price is NZ$403
includes taxes & fees
28 July - 29 July
The Dominion House Bed & Breakfast
Hampton Inn & Suites Mahwah
Enjoy meals and meetings in this versatile room with a long dining table and comfortable seating areas.

Hampton Inn & Suites Mahwah

2.5 star property
8.8 out of 10, Excellent, (1266)
"Will stay here again."
The price is NZ$208
includes taxes & fees
24 Aug - 25 Aug
Hampton Inn & Suites Mahwah
Hampton Inn Harriman Woodbury
Relax in the spacious lobby with a fireplace, sofas, and chairs, and enjoy the view through the glass door to the outdoor area.

Hampton Inn Harriman Woodbury

2.5 star property
9.2 out of 10, Wonderful, (1011)
"Great stay great staff great accommodations "
The price is NZ$258
includes taxes & fees
3 Aug - 4 Aug
Hampton Inn Harriman Woodbury
Quality Inn & Suites Fishkill South near I-84
Relax in comfort with two single beds and a large bed, a flat-screen TV, and a desk for work.

Quality Inn & Suites Fishkill South near I-84

2.5 star property
8.8 out of 10, Excellent, (1014)
"It is good to stay couple days !!"
The price is NZ$185
includes taxes & fees
3 Aug - 4 Aug
Quality Inn & Suites Fishkill South near I-84
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
Enjoy a wide selection of dishes at our buffet, featuring omelets, cheese, and more.

Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Would stay again"
The price is NZ$271
includes taxes & fees
27 July - 28 July
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
HYATT house Fishkill/Poughkeepsie
Enjoy cooking in this well-equipped kitchen with a large island, refrigerator, microwave, and coffee maker.

HYATT house Fishkill/Poughkeepsie

3.0 star property
8.8 out of 10, Excellent, (1011)
"Excellent...would stay again"
The price is NZ$235
includes taxes & fees
27 July - 28 July
HYATT house Fishkill/Poughkeepsie
Hampton Inn by Hilton Middletown
Welcome to Hampton Inn, where a covered walkway leads to the entrance, surrounded by beautifully landscaped gardens.

Hampton Inn by Hilton Middletown

2.5 star property
8.6 out of 10, Excellent, (1001)
"Stay was pleasant "
The price is NZ$202
includes taxes & fees
24 Aug - 25 Aug
Hampton Inn by Hilton Middletown
Holiday Inn Express & Suites Montgomery by IHG
Guests enter through a covered walkway and a welcoming bench area.

Holiday Inn Express & Suites Montgomery by IHG

2.5 star property
8.8 out of 10, Excellent, (741)
"Super clean and breakfast was amazing "
The price is NZ$202
includes taxes & fees
3 Aug - 4 Aug
Holiday Inn Express & Suites Montgomery by IHG
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Relax by the pool with a clear view of the surrounding area from the high ceilinged space.

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

2.0 star property
8.4 out of 10, Very good, (1005)
"Beautiful view and comfy bed and pillows "
The price is NZ$223
includes taxes & fees
27 July - 28 July
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Comfort Suites Fishkill near Interstate 84
Enjoy a convenient kitchen with a coffee machine, food bowls, and a refresh station.

Comfort Suites Fishkill near Interstate 84

2.5 star property
9.0 out of 10, Wonderful, (1004)
"A relaxing experience there with the staff and easy navigating "
The price is NZ$217
includes taxes & fees
3 Aug - 4 Aug
Comfort Suites Fishkill near Interstate 84
Holiday Inn Express Ramsey-Mahwah by IHG
Experience the sleek, modern design of this hotel, featuring a flat roof and symmetrical facade with glass and brick elements.

Holiday Inn Express Ramsey-Mahwah by IHG

2.5 star property
9.2 out of 10, Wonderful, (1005)
"The property was clean comfortable and a good choice for staying over night "
The price is NZ$234
includes taxes & fees
3 Aug - 4 Aug
Holiday Inn Express Ramsey-Mahwah by IHG
The Crossroads Hotel, Newburgh
Relax in our outdoor seating area with comfortable furniture and lush greenery.

The Crossroads Hotel, Newburgh

3.0 star property
7.4 out of 10, Good, (480)
"Front desk and the cleanliness of room was excellent "
The price is NZ$195
includes taxes & fees
29 July - 30 July
The Crossroads Hotel, Newburgh
Overlook Lodge at Bear Mountain
Enjoy meals in this inviting dining area with round tables, cushioned chairs, and a stone wall featuring a mounted deer head sculpture.

Overlook Lodge at Bear Mountain

2.5 star property
8.4 out of 10, Very good, (1004)
"Would like to stay here again."
The price is NZ$226
includes taxes & fees
7 Aug - 8 Aug
Overlook Lodge at Bear Mountain
Courtyard by Marriott Newburgh Stewart Airport
Enter the Courtyard Marriott under a covered canopy, marked by the hotel's prominent signage.

Courtyard by Marriott Newburgh Stewart Airport

3.0 star property
8.2 out of 10, Very good, (669)
"This is my 3rd hotel in my NY trip so was the best one ."
The price is NZ$231
includes taxes & fees
10 Aug - 11 Aug
Courtyard by Marriott Newburgh Stewart Airport
Appalachian Motel
Guests can park their vehicles in the designated parking area adjacent to the building.

Appalachian Motel

2.0 star property
7.8 out of 10, Good, (486)
"If you looking for quite and convenient place, its for you"
The price is NZ$128
includes taxes & fees
6 Aug - 7 Aug
Appalachian Motel
Rolling Hills Motel
Relax by the fire pit surrounded by six Adirondack chairs in a serene garden setting.

Rolling Hills Motel

2.0 star property
8.4 out of 10, Very good, (160)
"Very nice rooms and staff very quiet place for family Staff was very inviting "
The price is NZ$157
includes taxes & fees
27 July - 28 July
Rolling Hills 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

Escape to relaxing Chester! Enjoy its dining and skiing.

See all hotels in Chester

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

10/10 Excellent
"We love this place we been going here for a few years now and we can’t wait to go back , the pool and hot tub is wonderful and we love the cookies "
Sarah 3-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Nanuet

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?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This holiday home rental outside of Chester is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. 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's the best place to stay on a budget in Chester?

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

What's the best accommodation for a romantic getaway to Chester?

The Dominion House Bed & Breakfast is a favourite 3.5-star B&B for couples, and features wedding services and free breakfast. See all romantic hotels 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's the best accommodation option for a ski holiday 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 WiFiThis hotel is located 21 minutes by car from Mount Peter Ski Area. See all ski hotels 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 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 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 19 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.