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
Apr 24 - Apr 26
In two weeks
May 1 - May 3
In one month
May 15 - May 17
In two months
Jun 12 - Jun 14
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, (1,000 reviews)
"We have been several times during the past few years the hotel is in very good condition and the coffee is really good available 24 hours a day the breakfast has several choices that are good the rooms are clean the A/C and heat work great overall great place to stay we come sometimes for a quick weekend getaway from New York City will continue to come back. Great local diner and restaurants."
United States
Kenneth
$129 nightly
The price is $152
Apr 19 - Apr 20
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 20 - Apr 21
Total with taxes and fees
The Dominion House Bed & Breakfast
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)
"Everything was clean. "
United States
John
$109 nightly
The price is $123
Apr 26 - Apr 27
Total with taxes and fees
Days Inn by Wyndham Wurtsboro
Lobby

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very Good, (34 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
Restaurant

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1,001 reviews)
"Amazing stay with great amenities!"
United States
Audrey
$100 nightly
The price is $123
Apr 21 - Apr 22
Total with taxes and fees
Overlook Lodge at Bear Mountain
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, (123 reviews)
"Amazing easy check in/out and very kind staff. Had a wonderful stay, thank you! "
United States
Amanda
$88 nightly
The price is $98
Apr 27 - Apr 28
Total with taxes and fees
High Point Motel
Property amenity

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.6 out of 10, Excellent, (1,018 reviews)
"Great stay!!! "
United States
diana
$101 nightly
The price is $119
Apr 22 - Apr 23
Total with taxes and fees
Courtyard by Marriott Middletown Goshen
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, (1,000 reviews)
"Amazing staff Great breakfast Clean quiet rooms"
United States
R
$110 nightly
The price is $135
Apr 26 - Apr 27
Total with taxes and fees
Fairfield Inn & Suites by Marriott Goshen Middletown
Lobby

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,001 reviews)
"It was a beautiful experience. Clean and 5 star service. The staff so friendly and helpful. Peaceful fun experience. "
United States
Amanda
$92 nightly
The price is $109
Apr 27 - Apr 28
Total with taxes and fees
Hampton Inn by Hilton Middletown
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, (1,049 reviews)
"Wonderful staff, clean and perfect for family, business or leisure stay. And budget friendly."
United States
Jawanda
$101 nightly
The price is $114
Apr 26 - Apr 27
Total with taxes and fees
Sleep Inn & Suites Monroe - 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, (1,002 reviews)
"Great overall stay, nice restaurant beside hotel"
Canada
Dale
$85 nightly
The price is $98
May 17 - May 18
Total with taxes and fees
Quality Inn & Suites Fishkill South near I-84
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, (846 reviews)
"Easy check in and beautiful room"
United States
CORETHA
$113 nightly
The price is $128
Apr 26 - Apr 27
Total with taxes and fees
Holiday Inn Express & Suites Montgomery by IHG
Free daily continental breakfast

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
8.0 out of 10, Very Good, (64 reviews)
"The place was spotless and the staff were very friendly. The bed was so comfortable lovely stay "
United States
sharon
$93 nightly
The price is $107
Apr 23 - Apr 24
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, (206 reviews)
"Great local spot. Recently updated "
United States
Steve
$85 nightly
The price is $95
Apr 23 - Apr 24
Total with taxes and fees
Rolling Hills 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, (1,003 reviews)
"Wonderful accommodations!!"
United States
Roxanne
$114 nightly
The price is $135
Apr 26 - Apr 27
Total with taxes and fees
Hampton Inn & Suites Newburgh Stewart Airport
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, (27 reviews)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
$169 nightly
The price is $200
Apr 19 - Apr 20
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 4
Lobby

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,088 reviews)
"Clean, quiet and great breakfast."
United States
Dawn
$114 nightly
The price is $140
Apr 26 - Apr 27
Total with taxes and fees
Hampton Inn Harriman Woodbury
Reception

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh
3.0 star property
Newburgh
7.0 out of 10, Good, (739 reviews)
"The room was clean and staff was very helpful and professional. "
United States
paul
$99 nightly
The price is $117
Apr 19 - Apr 20
Total with taxes and fees
The Crossroads Hotel, Newburgh
Living area

Cozy 2BR condo w/ valley views

Cozy 2BR condo w/ valley views
Vernon Township
9.6 out of 10, Exceptional, (26 reviews)
"Very nice stay really clean and beautiful views thanks a lot enjoyed snowboarding at creek for the 2 days "
United States
Jacqueline
$218 nightly
The price is $247
Apr 19 - Apr 20
Total with taxes and fees
Cozy 2BR condo w/ valley views
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, (1,003 reviews)
"Best Hotel in area so far 😁 "
United States
Debi
$106 nightly
The price is $125
Apr 27 - Apr 28
Total with taxes and fees
Sleep Inn & Suites Middletown - Goshen
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

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

4/10 Poor
"Our whole room felt like it needed a wipe down… there were smudges on the walls and headboard. Sheets felt and looked clean. Pool was disgusting. It was so murky you couldn’t see the bottom. And there was easily 30 kids crammed into it. Also there was flooding around the pool. "
Victoria 1-night trip
Posted 2 hours ago
Courtyard by Marriott Middletown Goshen

Find out more about Chester

Chester Guest Houses information

Number of reviews
12,875
Accommodation
3 Guest Houses
Lowest Price
$95
Highest Price
$247

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 $95 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