Search Guest Houses in Chester

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
May 8 - May 10
In two weeks
May 15 - May 17
In one month
May 29 - May 31
In two months
Jun 26 - Jun 28
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, (1,003 reviews)
"yes parking was good and breakfast was plentiful"
United States
Eileen
$124 nightly
The price is $146
Apr 30 - May 1
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
Apr 29 - Apr 30
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, (129 reviews)
"Clean room, convenient parking. Good place to stay."
United States
Daniel
$88 nightly
The price is $98
Apr 28 - Apr 29
Total with taxes and fees
High Point Motel
Suite, 1 King Bed, Non Smoking (1 Bedroom) | 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, (618 reviews)
"Very clean and staff helpful "
United States
Kaiden
$112 nightly
The price is $127
Apr 28 - Apr 29
Total with taxes and fees
Days Inn by Wyndham Wurtsboro
Restaurant

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1,004 reviews)
"Beautiful setting and helpful staff. The room was clean and we enjoyed the outdoor activities."
United States
Jen
$116 nightly
The price is $142
Apr 29 - Apr 30
Total with taxes and fees
Overlook Lodge at Bear Mountain
Lobby

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very Good, (37 reviews)
"The hotel is new and clean"
United States
FENGMING
$98 nightly
The price is $121
May 10 - May 11
Total with taxes and fees
Comfort Suites Central Valley - Woodbury
Property amenity

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very Good, (1,002 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
$93 nightly
The price is $109
May 3 - May 4
Total with taxes and fees
Courtyard by Marriott Middletown Goshen
Lobby

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (1,000 reviews)
"A lot to do over there, good for a whole weekend, or even more. Had great time. "
United States
illay
$96 nightly
The price is $110
Apr 29 - Apr 30
Total with taxes and fees
Quality Inn near Mountain Creek
Free continental breakfast on weekdays

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,011 reviews)
"I like everything there, was clean the food good "
United States
Ada Yecenia
$106 nightly
The price is $125
Apr 30 - May 1
Total with taxes and fees
Sleep Inn & Suites Middletown - Goshen
Lobby

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,007 reviews)
"Breakfast was great and hotel was clean"
United States
Brigitte
$91 nightly
The price is $108
Apr 30 - May 1
Total with taxes and fees
Hampton Inn by Hilton Middletown
Reception

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh
3.0 star property
Newburgh
7.0 out of 10, Good, (740 reviews)
"The room was clean and staff was very helpful and professional. "
United States
paul
$82 nightly
The price is $97
May 20 - May 21
Total with taxes and fees
The Crossroads Hotel, Newburgh
Seasonal outdoor pool, pool umbrellas, sun loungers

LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.8 out of 10, Excellent, (41 reviews)
"Clean room, friendly staff, plentiful breakfast "
United States
Michelle
$308 nightly
The price is $363
May 25 - May 26
Total with taxes and fees
LEGOLAND Hotel NEW York
Reception

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
3.0 star property
Goshen
8.8 out of 10, Excellent, (1,003 reviews)
"the properties are clean , good breakfast and the staff are welcoming and smiling ."
United States
nadia
$119 nightly
The price is $147
May 4 - May 5
Total with taxes and fees
Fairfield Inn & Suites by Marriott Goshen 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, (396 reviews)
"This is well worth the stay, they're incredible!"
United States
James
$87 nightly
The price is $97
Apr 28 - Apr 29
Total with taxes and fees
Sussex Motel
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, (1,002 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
$84 nightly
The price is $103
Apr 28 - Apr 29
Total with taxes and fees
Americas Best Value Inn at Central Valley-Woodbury
Aerial view

West Point Motel

West Point Motel
2.5 star property
Highland Falls
8.6 out of 10, Excellent, (688 reviews)
"A nice quiet place to stay when visiting cadet son at West Point. An older motel that is well maintained and comfortable."
United States
John
$110 nightly
The price is $135
Apr 28 - Apr 29
Total with taxes and fees
West Point Motel
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 4 - May 5
Total with taxes and fees
Hampton Inn & Suites Newburgh Stewart Airport
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, (1,002 reviews)
"Great hotel for the price!"
United States
Jacqueline
$91 nightly
The price is $105
May 28 - May 29
Total with taxes and fees
Quality Inn & Suites Fishkill South near I-84
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, (1,059 reviews)
"The bed was comfy, the room very clean, and I appreciated all the options available for breakfast. I would stay here again."
United States
Marla
$119 nightly
The price is $135
Apr 30 - May 1
Total with taxes and fees
Sleep Inn & Suites Monroe - Woodbury
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
Apr 28 - Apr 29
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Spark by Hilton Fishkill

Spark by Hilton Fishkill

8/10 Good
" Real fast very limited for Vegetarian. "
Ashish 2-night trip
Posted 1 hour ago
Spark by Hilton Fishkill

Find out more about Chester

Chester Guest Houses information

Number of reviews
14,008
Accommodation
3 Guest Houses
Lowest Price
$97
Highest Price
$363

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 $97 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.

Explore a world of travel with Expedia