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Our top choices for Chester hotels

Exterior
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.6 out of 10, Excellent, (1007)
"timely & courteous check-in; clean rooms; quiet environment; perfect location for our needs "
United States
Orlando
The price is NZ$170
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Hotel & Suites Chester by IHG
Superior Double Room, Ensuite (Primrose) | Miscellaneous
The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233)
"Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY."
United States
Erek
The price is NZ$417
includes taxes & fees
31 Dec - 1 Jan 2026
The Dominion House Bed & Breakfast
Exterior
Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG
2.5 star property
Montgomery
8.8 out of 10, Excellent, (801)
"Clean quiet and nice reception "
United States
Nick
The price is NZ$167
includes taxes & fees
11 Jan - 12 Jan 2026
Holiday Inn Express & Suites Montgomery by IHG
Lobby
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1023)
"Easy check in, clean room, very good breakfast."
United States
Robert
The price is NZ$206
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Harriman Woodbury
Free daily buffet breakfast
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.2 out of 10, Wonderful, (1003)
"Yes stay was pleasant "
United States
henry
The price is NZ$181
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort Suites Fishkill near Interstate 84
Room, 1 King Bed, Non Smoking
Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1007)
"The room was very clean, comfortable bed, good service and at a reasonable price."
Canada
DIMITRIOS
The price is NZ$158
includes taxes & fees
25 Jan - 26 Jan 2026
Sleep Inn & Suites Monroe - Woodbury
Free daily continental breakfast
Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84
2.5 star property
Fishkill
9.0 out of 10, Wonderful, (1004)
"Always stay here on my way through NY."
United States
Kathleen
The price is NZ$173
includes taxes & fees
4 Jan - 5 Jan 2026
Quality Inn & Suites Fishkill South near I-84
Lobby
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1012)
"Clean room, friendly staff, good breakfast"
United States
Zuriber
The price is NZ$204
includes taxes & fees
11 Jan - 12 Jan 2026
DoubleTree by Hilton Hotel Nanuet
Reception
Tru by Hilton Middletown

Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (960)
"Staff both during check in and out were great . Great stay ."
United States
david
The price is NZ$224
includes taxes & fees
4 Jan - 5 Jan 2026
Tru by Hilton Middletown
Reception
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport
2.5 star property
Newburgh
9.2 out of 10, Wonderful, (980)
"Excellent stay and I will be back! "
United States
Jawara
The price is NZ$214
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Newburgh Stewart Airport
Indoor pool
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very good, (1004)
"Love it, everytime we come this is the place to stay"
United States
William
The price is NZ$196
includes taxes & fees
1 Jan - 2 Jan 2026
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
View from property
Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
2.5 star property
Goshen
8.8 out of 10, Excellent, (1001)
"Rooms were clean and as expected. Bed was a bit soft for our taste, but acceptable. Breakfast options were routine, scrambled eggs, bacon or sausage on alternating days, oatmeal, waffles, bagel, toast, English muffins... Pleasant and helpful staff, smooth check-in and check-out. Overall a pleasant place."
United States
Joon
The price is NZ$213
includes taxes & fees
7 Jan - 8 Jan 2026
Fairfield Inn & Suites by Marriott Goshen Middletown
Buffet
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
2.5 star property
Fishkill
8.4 out of 10, Very good, (1008)
"Very nice stay."
United States
Peter
The price is NZ$174
includes taxes & fees
24 Jan - 25 Jan 2026
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
Exterior
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1005)
"Room was clean and staff was great!"
United States
Annemarie
The price is NZ$146
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn by Hilton Middletown
Interior
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG
3.5 star property
Suffern
8.8 out of 10, Excellent, (1012)
"Room was clean and staff was friendly. "
United States
Jose
The price is NZ$219
includes taxes & fees
27 Jan - 28 Jan 2026
Crowne Plaza Suffern - Mahwah by IHG
Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1004)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
The price is NZ$203
includes taxes & fees
15 Jan - 16 Jan 2026
Overlook Lodge at Bear Mountain
Lobby
Quality Inn near Mountain Creek

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (981)
"The shower pressure was very low, the room was small, and the soundproofing was poor."
China
Ting
The price is NZ$168
includes taxes & fees
12 Jan - 13 Jan 2026
Quality Inn near Mountain Creek
Free daily full breakfast
Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah
2.5 star property
Mahwah
8.8 out of 10, Excellent, (1432)
"Great place to stay. "
United States
Omar
The price is NZ$224
includes taxes & fees
8 Jan - 9 Jan 2026
Hampton Inn & Suites Mahwah
Property amenity
Residence Inn by Marriott Fishkill

Residence Inn by Marriott Fishkill

Residence Inn by Marriott Fishkill
3.0 star property
Fishkill
9.4 out of 10, Exceptional, (407)
"High marks to this property!! Staff, cleanliness, room layout all excellent!!"
United States
Ron
The price is NZ$256
includes taxes & fees
24 Jan - 25 Jan 2026
Residence Inn by Marriott Fishkill
View from property
Inn on the Hudson

Inn on the Hudson

Inn on the Hudson
2.0 star property
Peekskill
7.0 out of 10, Good, (1004)
"yes but the beds were not comfortable"
United States
Gene
The price is NZ$174
includes taxes & fees
4 Jan - 5 Jan 2026
Inn on the Hudson
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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Stay near popular Chester attractions

The Rock Sports Complex

4.0/5 (10 reviews)
Explore the great outdoors at The Rock Sports Complex, a lovely green space in Chester. While you're in the area, find time to visit its shops.
See properties

Goosepond Mountain State Park

4.0/5 (3 reviews)
You can take time to visit Goosepond Mountain State Park during your travels to Chester. Visit the shops in this family-friendly area or simply enjoy its restaurants.
See properties

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
Black dirt region farm Chester New York

Top Chester Hotel Reviews

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent
"timely & courteous check-in; clean rooms; quiet environment; perfect location for our needs "
Orlando 1-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Chester by IHG

More cheap accommodation in Chester

Super 8 by Wyndham Mahwah

Super 8 by Wyndham Mahwah

160 State Route 17 South Mahwah NJ
The price is NZ$145 per night from 4 Jan to 5 Jan
NZ$145
4 Jan - 5 Jan 2026
includes taxes & fees
7.2/10 Good! (1,002 reviews)

Frequently asked questions

What's the best place to stay in Chester?
Based on our traveller data, Holiday Inn Express Hotel & Suites Chester by IHG is one of the top choices for your stay. This hotel offers free breakfast and an indoor pool. Other good choices for your stay in the area are DoubleTree by Hilton Hotel Nanuet and Sonesta Simply Suites Nanuet. 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 kitchenware, 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. 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 might want to add Goosepond Mountain State Park to your itinerary. 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.

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