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Check prices for these dates

Next weekend
30 Jan - 1 Feb
In two weeks
6 Feb - 8 Feb
In one month
20 Feb - 22 Feb
In two months
20 Mar - 22 Mar

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 €207
includes taxes & fees
26 Jan - 27 Jan
The Dominion House Bed & Breakfast
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (147 reviews)
"Breakfast was hot and tasty. Staff were all pleasant and accommodating. "
United States
wendy
Borland House Inn
Exterior

Villa Verde BB Greenwood Lake NY

Villa Verde BB Greenwood Lake NY
4.0 star property
Monroe
10.0 out of 10, Exceptional, (14 reviews)
"Amazing breakfast, scenery, tucked away on a hilltop, what a getaway! "
United States
Gary
The price is €205
includes taxes & fees
3 Feb - 4 Feb
Villa Verde BB Greenwood Lake NY
Exterior

The Castle at Skylands Manor

The Castle at Skylands Manor
3.5 star property
Ringwood
7.4 out of 10, Good, (391 reviews)
"If you want a quiet, historical experience, then this is the venue. It's not new, shiny - but that is not why you go there. It is a beautiful Tudor-style hotel, with old fixtures, antique windows, and the charm of a storybook castle. The innkeeper is lovely and the grounds are beautiful. We missed peak colors by a week or two and are considering a quick trip back! Buffet breakfast was just right."
United States
Lesli
The price is €188
includes taxes & fees
14 Feb - 15 Feb
The Castle at Skylands Manor
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 €247
includes taxes & fees
4 Feb - 5 Feb
Stagecoach Inn
Exterior

Alpine Haus Bed & Breakfast Inn

Alpine Haus Bed & Breakfast Inn
3.0 star property
Vernon
9.2 out of 10, Wonderful, (328 reviews)
"Excellent experience, all the way around. Quiet and quaint, all the modern amenities, excellent host and service, hot water in the shower, beautiful room, bountiful, delicious breakfast."
United States
Robert
The price is €196
includes taxes & fees
4 Feb - 5 Feb
Alpine Haus Bed & Breakfast Inn
Terrace/patio

Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.4 out of 10, Exceptional, (95 reviews)
"Great stay!"
United States
Amrita
The price is €298
includes taxes & fees
25 Jan - 26 Jan
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
"Great staff. I will be back soon. I wanted to hike but couldn’t find were to access because the construction "
Nadire 2-night trip
Posted 2 days ago
Overlook Lodge at Bear Mountain

Find out more about Chester

Chester B&B information

Number of reviews
949
Accommodation
12 B&B
Lowest Price
€188
Highest Price
€298

Frequently asked questions

Searching for B&Bs in Chester?
If you want to find some accommodation with fewer rooms than a hotel and an intimate environment, a B&B might be just the right fit for your getaway to Chester. If your ideal holiday to Chester includes spending lots of time outside, The Rock Sports Complex is a good spot to enjoy the scenery.
Why choose a B&B versus a traditional hotel?
With attentive service, opportunities to mingle with other guests and top-rated 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/games room and library. Borland House Inn: 5 rooms. 11.5 mi (18.5 km) from the city centre. Enjoy the free full breakfast and snack bar/deli. The Castle at Skylands Manor: 21 rooms. Situated 16.5 mi (26.5 km) from the heart of Chester. Cromwell Manor Inn: 13 rooms. 12.5 mi (20.1 km) from the city centre. Enjoy the free cooked breakfast and unique decor. Alpine Haus Bed & Breakfast Inn: 10 rooms. Located 16.7 mi (26.9 km) from the core of Chester. Enjoy the arcade/games room and library.
When should I stay at a B&B in Chester?
When you're dreaming of a trip to Chester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Chester are January, February, March and April, with each month seeing an average of 16 cm of snowfall.
What is there to do in Chester?
Travellers 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 should put Goosepond Mountain State Park and Museum Village on your list if you want to see more of the area.
How can I get to and around Chester?
You can plan your excursions in and around Chester ahead of time with these transportation options. Fly into Newburgh, NY (SWF-Stewart Intl.), which is located 13.5 mi (21.7 km) away. 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.