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Check prices for these dates

Next weekend
20 Mar - 22 Mar
In two weeks
27 Mar - 29 Mar
In one month
10 Apr - 12 Apr
In two months
8 May - 10 May

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 €209
includes taxes & fees
11 Mar - 12 Mar
The Dominion House Bed & Breakfast
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (153 reviews)
"Breakfast was hot and tasty. Staff were all pleasant and accommodating. "
United States
wendy
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, (17 reviews)
"Amazing breakfast, scenery, tucked away on a hilltop, what a getaway! "
United States
Gary
The price is €193
includes taxes & fees
10 Mar - 11 Mar
Villa Verde BB Greenwood Lake NY
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
Columbus Hotel
Exterior

Alpine Haus Bed & Breakfast Inn

Alpine Haus Bed & Breakfast Inn
3.0 star property
Vernon
9.2 out of 10, Wonderful, (330 reviews)
"We had a great weekend stay at Alpine! The caretaker, Anil was so hospitable! We will definitely be back soon!"
United States
Krystal
The price is €197
includes taxes & fees
10 Mar - 11 Mar
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, (392 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 €168
includes taxes & fees
19 Mar - 20 Mar
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 €299
includes taxes & fees
22 Mar - 23 Mar
Stagecoach 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
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

Hilton Garden Inn Nanuet

Hilton Garden Inn Nanuet

8/10 Good
"We booked with free breakfast, but was charged."
Tyhisha 2-night trip
Posted 5 hours ago
Hilton Garden Inn Nanuet

Find out more about Chester

Chester B&B information

Number of reviews
834
Accommodation
12 B&B
Lowest Price
€168
Highest Price
€299

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. Villa Verde BB Greenwood Lake NY: 2 rooms. 9.1 mi (14.6 km) from the city centre. Enjoy the free full breakfast and unique decor. Alpine Haus Bed & Breakfast Inn: 10 rooms. Situated 16.7 mi (26.9 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. Cromwell Manor Inn: 13 rooms. Located 12.5 mi (20.1 km) from the core of Chester. Enjoy the free cooked breakfast and unique decor.
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 Museum Village are some notable sights to visit. You should put The Rock Sports Complex 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.