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Check prices for these dates

Next weekend
15 May - 17 May
In two weeks
22 May - 24 May
In one month
5 Jun - 7 Jun
In two months
3 Jul - 5 Jul

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 AED 790
AED 893 total
includes taxes & fees
11 May - 12 May
The Dominion House Bed & Breakfast
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (161 reviews)
"A quaint inn with lovely breakfast. Rooms are small. Bed was comfortable but our room faced the street which was noisy."
United States
Renee
The price is AED 376
AED 438 total
includes taxes & fees
11 May - 12 May
Borland House Inn
Exterior

Parkway House Goshen Bed & Breakfast

Parkway House Goshen Bed & Breakfast
3.0 star property
Goshen
10.0 out of 10, Exceptional, (2 reviews)
"The space was beautiful and thoughtfully designed which made our stay very comfortable and pleasurable. Rooms are even more elegant than in the photos. The hosts are warm and accommodating - a class act. Great location, easily walking distance to Main Street. Would stay again/recommend to others. "
United States
Chris
The price is AED 638
AED 785 total
includes taxes & fees
21 May - 22 May
Parkway House Goshen Bed & Breakfast
Exterior

Alpine Haus Bed & Breakfast Inn

Alpine Haus Bed & Breakfast Inn
3.0 star property
Vernon
9.2 out of 10, Wonderful, (332 reviews)
"The Owner is very nice, kind and sociable. The breakfasts were delicious. "
United States
Cynthia
The price is AED 735
AED 842 total
includes taxes & fees
7 May - 8 May
Alpine Haus Bed & Breakfast Inn
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 AED 610
AED 718 total
includes taxes & fees
13 May - 14 May
The Castle at Skylands Manor
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, (19 reviews)
"Amazing breakfast, scenery, tucked away on a hilltop, what a getaway! "
United States
Gary
The price is AED 785
AED 889 total
includes taxes & fees
14 May - 15 May
Villa Verde BB Greenwood Lake NY
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 AED 978
AED 1,204 total
includes taxes & fees
7 May - 8 May
Stagecoach Inn
Terrace/patio

Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.6 out of 10, Exceptional, (99 reviews)
"Great stay!"
United States
Amrita
The price is AED 1,141
AED 1,347 total
includes taxes & fees
31 May - 1 Jun
Cromwell Manor 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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"It was a beautiful stay."
Shayla 1-night trip
Posted 4 hours ago
Overlook Lodge at Bear Mountain

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. Cromwell Manor Inn: 13 rooms. 12.5 mi (20.1 km) from the downtown core. Enjoy the free cooked breakfast and unique décor. Borland House Inn: 5 rooms. Situated 11.5 mi (18.5 km) from the heart of Chester. Enjoy the free full breakfast and deli. Villa Verde BB Greenwood Lake NY: 2 rooms. 9.1 mi (14.6 km) from the heart of downtown. Enjoy the free full breakfast and deli. The Castle at Skylands Manor: 21 rooms. Located 16.5 mi (26.5 km) from the core of Chester.
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.