Search Guest Houses in Chester

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

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, (1000)
"timely & courteous check-in; clean rooms; quiet environment; perfect location for our needs "
United States
Orlando
The price is NZ$239
includes taxes & fees
5 Jan - 6 Jan 2026
Holiday Inn Express Hotel & Suites Chester by IHG

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
26 Jan - 27 Jan 2026
The Dominion House Bed & Breakfast

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1006)
"Room was clean and staff was great!"
United States
Annemarie
The price is NZ$159
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn by Hilton Middletown

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (982)
"Good breakfast, and everything was clean in a great room. "
United States
Steven
The price is NZ$169
includes taxes & fees
12 Jan - 13 Jan 2026
Quality Inn near Mountain Creek

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (599)
"Very clean and quiet "
United States
Jeanette
The price is NZ$193
includes taxes & fees
2 Jan - 3 Jan 2026
Days Inn by Wyndham Wurtsboro

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.2 out of 10, Wonderful, (1004)
"Yes stay was pleasant "
United States
henry
The price is NZ$181
includes taxes & fees
9 Jan - 10 Jan 2026
Comfort Suites Fishkill near Interstate 84

LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.8 out of 10, Excellent, (33)
"We are having a great time at the hotel!!!"
United States
Ziwei
The price is NZ$596
includes taxes & fees
2 Jan - 3 Jan 2026
LEGOLAND Hotel NEW York

Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (961)
"Staff both during check in and out were great . Great stay ."
United States
david
The price is NZ$182
includes taxes & fees
7 Jan - 8 Jan 2026
Tru by Hilton Middletown

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

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$160
includes taxes & fees
11 Jan - 12 Jan 2026
Holiday Inn Express & Suites Montgomery by IHG

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$214
includes taxes & fees
14 Jan - 15 Jan 2026
Fairfield Inn & Suites by Marriott Goshen Middletown

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$201
includes taxes & fees
1 Jan - 2 Jan 2026
Overlook Lodge at Bear Mountain

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1024)
"Easy check in, clean room, very good breakfast."
United States
Robert
The price is NZ$206
includes taxes & fees
25 Jan - 26 Jan 2026
Hampton Inn Harriman Woodbury

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, (1006)
"Always stay here on my way through NY."
United States
Kathleen
The price is NZ$173
includes taxes & fees
5 Jan - 6 Jan 2026
Quality Inn & Suites Fishkill South near I-84

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, (1005)
"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

Sussex Motel

Sussex Motel
2.5 star property
Sussex
8.8 out of 10, Excellent, (372)
"Perfect for the price. Nice personel."
United States
Adam
The price is NZ$172
includes taxes & fees
25 Jan - 26 Jan 2026
Sussex Motel

Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill
3.0 star property
Fishkill
8.6 out of 10, Excellent, (1009)
"everything was great "
United States
Christopher
The price is NZ$193
includes taxes & fees
9 Jan - 10 Jan 2026
Hilton Garden Inn Fishkill

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1013)
"Clean room, friendly staff, good breakfast"
United States
Zuriber
The price is NZ$205
includes taxes & fees
11 Jan - 12 Jan 2026
DoubleTree by Hilton Hotel Nanuet

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport
2.5 star property
Newburgh
9.2 out of 10, Wonderful, (982)
"Excellent stay and I will be back! "
United States
Jawara
The price is NZ$214
includes taxes & fees
25 Jan - 26 Jan 2026
Hampton Inn & Suites Newburgh Stewart Airport

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, (1000)
"Great customer service and breakfast was excellent "
United States
Dennis
The price is NZ$187
includes taxes & fees
24 Jan - 25 Jan 2026
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chester Hotel Reviews

Find out more about Chester

Chester Guest Houses information

Number of reviews
16,859
Accommodation
6 Guest Houses
Lowest Price
NZ$158
Highest Price
NZ$596

Explore a world of travel with Expedia