Search Guest Houses in Chester

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Dec 19 - Dec 21
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Dec 26 - Dec 28
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Jan 9 - Jan 11
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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, (1001)
"The staff was excellent "
United States
Kelley
$109 nightly
The price is $129
Dec 11 - Dec 12
Total with taxes and fees
Holiday Inn Express Hotel & Suites Chester by IHG
Superior Double Room, Ensuite (Primrose) | Miscellaneous
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
$215 nightly
The price is $243
Dec 15 - Dec 16
Total with taxes and fees
The Dominion House Bed & Breakfast
Exterior
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

2.5 star property
Middletown
8.6 out of 10, Excellent, (1000)
"Room was clean and staff was great!"
United States
Annemarie
$75 nightly
The price is $89
Dec 21 - Dec 22
Total with taxes and fees
Hampton Inn by Hilton Middletown
Outdoor pool
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
$294 nightly
The price is $346
Dec 22 - Dec 23
Total with taxes and fees
LEGOLAND Hotel NEW York
Lobby
Quality Inn near Mountain Creek

Quality Inn near Mountain Creek

2.5 star property
Vernon
7.6 out of 10, Good, (972)
"Nice hotel. Close to golf,"
United States
Joseph
$85 nightly
The price is $98
Jan 4 - Jan 5, 2026
Total with taxes and fees
Quality Inn near Mountain Creek
Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1005)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
$104 nightly
The price is $118
Jan 8 - Jan 9, 2026
Total with taxes and fees
Overlook Lodge at Bear Mountain
Room, 2 Queen Beds, Non Smoking | In-room safe, desk, iron/ironing board, free cribs/infant beds
Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro

2.0 star property
Wurtsboro
7.6 out of 10, Good, (592)
"I love "
United States
Niralkumar
$99 nightly
The price is $112
Dec 11 - Dec 12
Total with taxes and fees
Days Inn by Wyndham Wurtsboro
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, (795)
"Good stay"
United States
Fatima
$90 nightly
The price is $102
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express & Suites Montgomery by IHG
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, (1000)
"Clean and easy check in. "
United States
chris
$88 nightly
The price is $100
Jan 5 - Jan 6, 2026
Total with taxes and fees
Sleep Inn & Suites Monroe - Woodbury
View from property
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
$97 nightly
The price is $119
Dec 24 - Dec 25
Total with taxes and fees
Fairfield Inn & Suites by Marriott Goshen Middletown
Lobby
Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill

3.0 star property
Fishkill
8.6 out of 10, Excellent, (1005)
"Brayden was great"
United States
Will
$92 nightly
The price is $104
Dec 24 - Dec 25
Total with taxes and fees
Hilton Garden Inn Fishkill
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, (934)
"great staff, clean rooms, nice breakfast .. overall a pleasant & safe atmosphere !"
United States
Emerson
$116 nightly
The price is $138
Jan 4 - Jan 5, 2026
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Lobby
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1003)
"Very clean rooms, nice courteous staff continental breakfast was great."
United States
KATHERINE
$103 nightly
The price is $127
Dec 17 - Dec 18
Total with taxes and fees
Hampton Inn Harriman Woodbury
Fireplace
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3.0 star property
Middletown
8.6 out of 10, Excellent, (1002)
"The hotel was very clean, enjoyed my stay would recommend "
United States
Jessica
$93 nightly
The price is $109
Dec 28 - Dec 29
Total with taxes and fees
Courtyard by Marriott Middletown Goshen
Free daily continental breakfast
Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

2.5 star property
Fishkill
8.8 out of 10, Excellent, (1002)
"Great staff, friendly, very clean room!"
United States
Amanda
$89 nightly
The price is $101
Dec 17 - Dec 18
Total with taxes and fees
Quality Inn & Suites Fishkill South near I-84
Reception
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 star property
Newburgh
9.2 out of 10, Wonderful, (976)
"Clean great staff great breakfast pool area warm "
United States
LaRhonda
$103 nightly
The price is $122
Dec 28 - Dec 29
Total with taxes and fees
Hampton Inn & Suites Newburgh Stewart Airport
Interior
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 star property
Suffern
8.8 out of 10, Excellent, (1001)
"Good location"
United States
Glenn
$108 nightly
The price is $126
Dec 19 - Dec 20
Total with taxes and fees
Crowne Plaza Suffern - Mahwah by IHG
Exterior
Holiday Inn Express Ramsey-Mahwah by IHG

Holiday Inn Express Ramsey-Mahwah by IHG

2.5 star property
Ramsey
9.2 out of 10, Wonderful, (1003)
"Clean room, very nice staff, bountiful breakfast. Would definitely stay there again. "
United States
Joanna Marie
$110 nightly
The price is $126
Jan 1 - Jan 2, 2026
Total with taxes and fees
Holiday Inn Express Ramsey-Mahwah by IHG
BBQ/picnic area
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 star property
Middletown
8.6 out of 10, Excellent, (1000)
"Love this hotel "
United States
Jennifer
$102 nightly
The price is $121
Jan 6 - Jan 7, 2026
Total with taxes and fees
Sleep Inn & Suites Middletown - Goshen
Free self parking
Appalachian Motel

Appalachian Motel

2.0 star property
Vernon
7.6 out of 10, Good, (515)
"I would stay here again"
United States
Lyanlex
$70 nightly
The price is $80
Jan 1 - Jan 2, 2026
Total with taxes and fees
Appalachian 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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Top Chester Hotel Reviews

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"Clean nice"
candy 1-night trip
Posted 14 hours ago
Crowne Plaza Suffern - Mahwah by IHG

Find out more about Chester

Chester Guest Houses information

Number of reviews
16,937
Accommodation
6 Guest Houses
Lowest Price
$80
Highest Price
$346

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 $80 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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