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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 AED 790
AED 893 total
includes taxes & fees
12 Mar - 13 Mar
The Dominion House Bed & Breakfast
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
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 AED 610
AED 718 total
includes taxes & fees
18 Mar - 19 Mar
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, (17 reviews)
"Amazing breakfast, scenery, tucked away on a hilltop, what a getaway! "
United States
Gary
The price is AED 625
AED 708 total
includes taxes & fees
19 Mar - 20 Mar
Villa Verde BB Greenwood Lake NY
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
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 1,035
AED 1,274 total
includes taxes & fees
11 Mar - 12 Mar
Stagecoach 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
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)
"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 AED 735
AED 842 total
includes taxes & fees
11 Mar - 12 Mar
Alpine Haus Bed & Breakfast 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

Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

2/10 Terrible
"The cleanness of the hotel is disgusting. I would never recommend anyone to that hotel. It’s the worst and I mean the worst stuff no good the rooms no good even the toilet flood over so the cleanness and the staff is no good. I was so disappointed and disgusted of that Hotel. "
Audia 4-night trip
Posted 6 hours ago
Sonesta Simply Suites Nanuet

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. Villa Verde BB Greenwood Lake NY: 2 rooms. 9.1 mi (14.6 km) from the downtown core. Enjoy the free full breakfast and unique décor. Alpine Haus Bed & Breakfast Inn: 10 rooms. Situated 16.7 mi (26.9 km) from the heart of Chester. Enjoy the arcade game room and library. Borland House Inn: 5 rooms. 11.5 mi (18.5 km) from the heart of downtown. Enjoy the free full breakfast and 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 décor.
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 Museum Village are some notable sights to visit. You might 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?
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.