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Check prices for these dates

Next weekend
1 May - 3 May
In two weeks
8 May - 10 May
In one month
22 May - 24 May
In two months
19 Jun - 21 Jun

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 €208
includes taxes & fees
27 Apr - 28 Apr
The Dominion House Bed & Breakfast
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (158 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 €102
includes taxes & fees
5 May - 6 May
Borland House 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 €195
includes taxes & fees
26 Apr - 27 Apr
Columbus Hotel
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)
"Amazing breakfast, scenery, tucked away on a hilltop, what a getaway! "
United States
Gary
The price is €235
includes taxes & fees
30 Apr - 1 May
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, (332 reviews)
"Really nice "
United States
Jennifer
The price is €196
includes taxes & fees
30 Apr - 1 May
Alpine Haus Bed & Breakfast Inn
Exterior

Parkway House Goshen Bed & Breakfast

Parkway House Goshen Bed & Breakfast
3.0 star property
Goshen
10.0 out of 10, Exceptional, (1 review)
"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 €315
includes taxes & fees
21 May - 22 May
Parkway House Goshen Bed & Breakfast
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 €167
includes taxes & fees
6 May - 7 May
The Castle at Skylands Manor
Terrace/patio

Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.6 out of 10, Exceptional, (98 reviews)
"Great stay!"
United States
Amrita
The price is €256
includes taxes & fees
3 May - 4 May
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 €333
includes taxes & fees
13 May - 14 May
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

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

8/10 Good
"Staff was very helpful, the room was clean and comfortable!"
Caitlin 1-night trip
Posted 12 hours ago
Sleep Inn & Suites Monroe - Woodbury

Find out more about Chester

Chester B&B information

Number of reviews
1,081
Accommodation
12 B&B
Lowest Price
€102
Highest Price
€333

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. Cromwell Manor Inn: 13 rooms. 12.5 mi (20.1 km) from the city centre. Enjoy the free cooked breakfast and unique decor. Borland House Inn: 5 rooms. Situated 11.5 mi (18.5 km) from the heart of Chester. Enjoy the free full breakfast and snack bar/deli. Villa Verde BB Greenwood Lake NY: 2 rooms. 9.1 mi (14.6 km) from the city centre. Enjoy the free full breakfast and snack bar/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 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 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?
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.