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Check prices for these dates

Next weekend
Apr 10 - Apr 12
In two weeks
Apr 17 - Apr 19
In one month
May 1 - May 3
In two months
May 29 - May 31

Our top choices for Chester bed & breakfast

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
The price is ￥34,099
￥38,575 total
includes taxes & fees
Apr 6 - Apr 7
The Dominion House Bed & Breakfast
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (157 reviews)
"What a wonderful experience staying at the Borland House is! With the quaint, homey feeling of the whole house, to the kindness of the staff. Your stay will absolutely be lovely. Ample towels are provided for the private, spacious bathroom. Very comfortable bedding and well appointed decorations are in the bedroom. I was in the Hummingbird Suite. I could see myself living there, it just had everything I needed. I look forward to visiting again in the future!"
United States
Elizabeth
The price is ￥16,250
￥18,932 total
includes taxes & fees
Apr 5 - Apr 6
Borland House Inn
Front of property

Villa Verde BB Greenwood Lake NY

Villa Verde BB Greenwood Lake NY
4.0 star property
Monroe
10.0 out of 10, Exceptional, (18 reviews)
"Lovely property, owner and food! A gem!"
United States
Riley
The price is ￥33,544
￥37,947 total
includes taxes & fees
Apr 9 - Apr 10
Villa Verde BB Greenwood Lake NY
Exterior

Alpine Haus Bed & Breakfast Inn

Alpine Haus Bed & Breakfast Inn
3.0 star property
Vernon
9.2 out of 10, Wonderful, (330 reviews)
"Really nice "
United States
Jennifer
The price is ￥31,720
￥36,359 total
includes taxes & fees
Apr 4 - Apr 5
Alpine Haus Bed & Breakfast Inn
Individually decorated, individually furnished, desk, iron/ironing board

Columbus Hotel

Columbus Hotel
3.0 star property
Middletown
6.0 out of 10, (6 reviews)
"21 minutes ago on Google It's a family owned and operated hotel. Norman was kind, communicative and thorough. Keyless entry made checking in super easy. We had a business suite, which is basically a studio apartment. Kitchen , bathroom, bed/living space was clean and neat having a really nice modern clean aesthetic. There was even a candle left for us to enjoy. Overall was a very pleasant stay! Very grateful. "
United States
Diane
The price is ￥17,953
￥35,561 total
includes taxes & fees
Apr 10 - Apr 11
Columbus Hotel
Exterior

The Castle at Skylands Manor

The Castle at Skylands Manor
3.5 star property
Ringwood
7.4 out of 10, Good, (393 reviews)
"Special thanks to Billy the innkeeper! He was great and made our stay very enjoyable! "
United States
Kyle
The price is ￥26,328
￥30,983 total
includes taxes & fees
Apr 15 - Apr 16
The Castle at Skylands Manor
Terrace/patio

Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.6 out of 10, Exceptional, (97 reviews)
"Great stay!"
United States
Amrita
The price is ￥46,084
￥54,437 total
includes taxes & fees
May 3 - May 4
Cromwell Manor Inn
Restaurant

Stagecoach Inn

Stagecoach Inn
3.5 star property
Goshen
9.6 out of 10, Exceptional, (79 reviews)
"We only stayed one night, but it was very comfortable and the staff was friendly. "
United States
Kathryn
The price is ￥39,214
￥48,281 total
includes taxes & fees
Apr 5 - Apr 6
Stagecoach Inn
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

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

8/10 Good
"Parking was great. Rooms were clean. "
Marcy 1-night trip
Posted 4 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Find out more about Chester

Chester B&B information

Number of reviews
1,234
Accommodation
12 B&B
Lowest Price
￥18,932
Highest Price
￥54,437

Frequently asked questions

Searching for B&Bs in Chester?
If you want to find a place to stay with fewer rooms than a hotel and a cozy environment, a B&B might be just the right fit for your getaway to Chester. If your ideal vacation to Chester includes spending lots of time outside, The Rock Sports Complex is a good spot to enjoy the scenery.
Why would you choose a B&B versus a traditional hotel?
With attentive service, opportunities to mingle with other guests, and tasty breakfasts, B&Bs offer a truly one-of-a-kind setting.
What are the best bed and breakfasts in Chester?
Below are some well-liked B&Bs in the surrounding area: The Dominion House Bed & Breakfast: 3 rooms. 4.7 mi (7.5 km) from the heart of Chester. Enjoy the arcade game room and library. Alpine Haus Bed & Breakfast Inn: 10 rooms. 16.7 mi (26.9 km) from the downtown core. Enjoy the arcade game room and library. Villa Verde BB Greenwood Lake NY: 2 rooms. Situated 9.1 mi (14.6 km) from the heart of Chester. Enjoy the free full breakfast and deli. Cromwell Manor Inn: 13 rooms. 12.5 mi (20.1 km) from the heart of downtown. Enjoy the free cooked breakfast and unique décor. Borland House Inn: 5 rooms. Located 11.5 mi (18.5 km) from the core of Chester. Enjoy the free full breakfast and deli.
When should I stay at a B&B in Chester?
When you're dreaming of a stay in Chester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Chester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
What is there to do in Chester?
Travelers enjoy Chester for its restaurants and shopping. When you want to explore some things to do in town, Castle Fun Center and The Rock Sports Complex are some notable sights to visit. You might put Museum Village and Goosepond Mountain State Park on your list if you want to see more of the area.
How can I get to and around Chester?
Mapping out your trip in and around Chester is easy with these transportation options. Fly into Stewart Intl. Airport (SWF), which is located 13.5 mi (21.7 km) from the city center. Otherwise, you can search for flights to Caldwell, NJ (CDW-Essex County), which is 33.6 mi (54.1 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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