Search Guest Houses in Chester

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Check prices for these dates

Next weekend
May 15 - May 17
In two weeks
May 22 - May 24
In one month
Jun 5 - Jun 7
In two months
Jul 3 - Jul 5
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Exterior

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, (1,005 reviews)
"yes parking was good and breakfast was plentiful"
United States
Eileen
$98 nightly
The price is $121
May 7 - May 8
Total with taxes and fees
Holiday Inn Express Hotel & Suites Chester by IHG
Exterior

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233 reviews)
"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
$215 nightly
The price is $243
May 11 - May 12
Total with taxes and fees
The Dominion House Bed & Breakfast
Comfort Room, 2 Double Beds | Iron/ironing board, free WiFi

High Point Motel

High Point Motel
2.0 star property
Sussex
9.2 out of 10, Wonderful, (131 reviews)
"Was a nice room in a nice town! Would stay there again with a super easy check in and checkout "
United States
Reuben
$85 nightly
The price is $95
May 6 - May 7
Total with taxes and fees
High Point Motel
Lobby

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.2 out of 10, Very Good, (40 reviews)
"Helpful and nice staff"
United States
Albino
$98 nightly
The price is $121
May 12 - May 13
Total with taxes and fees
Comfort Suites Central Valley - Woodbury
Restaurant

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1,006 reviews)
"Beautiful setting and helpful staff. The room was clean and we enjoyed the outdoor activities."
United States
Jen
$114 nightly
The price is $141
May 10 - May 11
Total with taxes and fees
Overlook Lodge at Bear Mountain
Reception

The Hamlet Inn at Warwick

The Hamlet Inn at Warwick
2.5 star property
Warwick
7.6 out of 10, Good, (159 reviews)
"good accommodations "
United States
Alejandro
$86 nightly
The price is $97
May 6 - May 7
Total with taxes and fees
The Hamlet Inn at Warwick
Room, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,064 reviews)
"Staff was very helpful, the room was clean and comfortable!"
United States
Caitlin
$101 nightly
The price is $114
May 12 - May 13
Total with taxes and fees
Sleep Inn & Suites Monroe - Woodbury
Reception

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport
2.5 star property
Newburgh
9.2 out of 10, Wonderful, (1,005 reviews)
"Large shower, clean, good breakfast, right off the highway, convenient parking "
United States
Michelle
$114 nightly
The price is $135
May 12 - May 13
Total with taxes and fees
Hampton Inn & Suites Newburgh Stewart Airport
Lobby

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (1,002 reviews)
"A lot to do over there, good for a whole weekend, or even more. Had great time. "
United States
illay
$90 nightly
The price is $103
May 19 - May 20
Total with taxes and fees
Quality Inn near Mountain Creek
Property amenity

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very Good, (1,001 reviews)
"Breakfast is over at 10am, the pool is open in the evening very small but overall good for kids. Great stay and price."
United States
Stacey
$101 nightly
The price is $119
May 10 - May 11
Total with taxes and fees
Courtyard by Marriott Middletown Goshen
Exterior

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, (854 reviews)
"the breakfast was ok, parking felt safe even though a part a it was not well lighted. "
United States
France
$113 nightly
The price is $128
Jun 3 - Jun 4
Total with taxes and fees
Holiday Inn Express & Suites Montgomery by IHG
Lobby

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,003 reviews)
"Breakfast was great and hotel was clean"
United States
Brigitte
$100 nightly
The price is $118
May 10 - May 11
Total with taxes and fees
Hampton Inn by Hilton Middletown
Comfort Room, 2 Double Beds, Non Smoking, Refrigerator & Microwave | Free WiFi, bed sheets

Sussex Motel

Sussex Motel
2.5 star property
Sussex
8.8 out of 10, Excellent, (397 reviews)
"The room was clean and designed nicely and had a nice feel…very unexpected for a motel type place."
United States
Ray
$75 nightly
The price is $84
May 10 - May 11
Total with taxes and fees
Sussex Motel
Free daily continental breakfast

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
8.0 out of 10, Very Good, (80 reviews)
"Great Stay"
United States
Siddiq
$98 nightly
The price is $113
May 12 - May 13
Total with taxes and fees
Spark by Hilton Fishkill
Classic Quadruple Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave | Free WiFi, bed sheets

Rolling Hills Motel

Rolling Hills Motel
2.0 star property
Sussex
8.4 out of 10, Very Good, (211 reviews)
"This older property is in good shape and conveniently located. Staff was very friendly and we had a large room with 2 queen beds. It was quiet both nights we stayed there"
United States
Timothy
$73 nightly
The price is $81
May 24 - May 25
Total with taxes and fees
Rolling Hills Motel
Exterior

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (1,002 reviews)
"Very nice hotel, clean and love the breakfast menu."
United States
Sonam
$112 nightly
The price is $133
May 10 - May 11
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Indoor pool

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, (1,003 reviews)
"Always a great stay "
United States
Janice
$104 nightly
The price is $118
May 10 - May 11
Total with taxes and fees
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Business center

Americas Best Value Inn at Central Valley-Woodbury

Americas Best Value Inn at Central Valley-Woodbury
2.0 star property
Central Valley
7.2 out of 10, Good, (1,003 reviews)
"This is definitely an older motel, but I have stayed here three times and was perfectly happy to give up a few amenities for the cost savings and location. Staff is super friendly, and I’ll be staying here again."
United States
Sarah
$100 nightly
The price is $123
May 14 - May 15
Total with taxes and fees
Americas Best Value Inn at Central Valley-Woodbury
Suite, 1 King Bed, Non Smoking | Desk, iron/ironing board, free cribs/infant beds, rollaway beds

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, (1,008 reviews)
"Great hotel for the price!"
United States
Jacqueline
$99 nightly
The price is $115
May 26 - May 27
Total with taxes and fees
Quality Inn & Suites Fishkill South near I-84
Outdoor dining

Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (28 reviews)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
$169 nightly
The price is $200
May 6 - May 7
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 4
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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Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

10/10 Excellent
"Everything was great! Just wished they offered a continental breakfast"
Jennifer 2-night trip
Posted 2 hours ago
DoubleTree by Hilton Hotel Nanuet

Find out more about Chester

Chester Guest Houses information

Number of reviews
11,835
Accommodation
3 Guest Houses
Lowest Price
$81
Highest Price
$243

Frequently asked questions

What is the nightly rate for a guest house in Chester?
Rates for Chester guest houses vary, but travelers can find great-value prices from $81 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Chester guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Chester guest house and a B&B?
A guest house in Chester is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.

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