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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Browse Select Chester B&B

Superior Double Room, Ensuite (Primrose) | Miscellaneous
The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast

2.0 star property
Chester
9.2 out of 10, Wonderful, (233)
"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 ₹19,348
₹21,888 total
includes taxes & fees
16 Dec - 17 Dec
The Dominion House Bed & Breakfast
Exterior detail
Borland House Inn

Borland House Inn

3.0 star property
Montgomery
9.2 out of 10, Wonderful, (144)
"Had a great stay at the the Borland House Inn a historical setting in a cute town with wonderful staff and a delicious breakfast"
United States
Deborah
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, (13)
"Amazing breakfast, scenery, tucked away on a hilltop, what a getaway! "
United States
Gary
The price is ₹15,744
₹19,611 total
includes taxes & fees
10 Dec - 11 Dec
Villa Verde BB Greenwood Lake NY
Exterior
Cromwell Manor Inn

Cromwell Manor Inn

4.0 star property
Cornwall
9.4 out of 10, Exceptional, (94)
"Great stay!"
United States
Amrita
Cromwell Manor Inn
Property grounds
The Castle at Skylands Manor

The Castle at Skylands Manor

3.5 star property
Ringwood
7.4 out of 10, Good, (391)
"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 ₹17,099
₹19,991 total
includes taxes & fees
10 Dec - 11 Dec
The Castle at Skylands Manor
Terrace/patio
Alpine Haus Bed & Breakfast Inn

Alpine Haus Bed & Breakfast Inn

3.0 star property
Vernon
9.2 out of 10, Wonderful, (325)
"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 ₹17,999
₹20,631 total
includes taxes & fees
12 Dec - 13 Dec
Alpine Haus Bed & Breakfast Inn
Restaurant
Stagecoach Inn

Stagecoach Inn

3.5 star property
Goshen
9.6 out of 10, Exceptional, (78)
"Staff was amazing friendly attentive always smiling. Food and drinks were delicious. Loved the ambience of the room. "
United States
Theresa
The price is ₹21,148
₹26,038 total
includes taxes & fees
4 Jan - 5 Jan 2026
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

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

10/10 Excellent
"Clean room and easy check in. "
Melanie 2-night trip
Posted 1 day ago
Hampton Inn by Hilton Middletown

Find out more about Chester

Chester B&B information

Number of reviews
942
Accommodation
10 B&B
Lowest Price
₹19,611
Highest Price
₹26,038

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. The Castle at Skylands Manor: 21 rooms. 16.5 mi (26.5 km) from the city centre. Villa Verde BB Greenwood Lake NY: 2 rooms. Located 9.1 mi (14.6 km) from the core of Chester. Enjoy the free full 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 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.

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