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Check prices for these dates

Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct
In one month
6 Nov - 8 Nov
In two months
4 Dec - 6 Dec

Our top choices for Chester bed & breakfast

A large, two-story white house with a wrap-around porch and a small front garden.

1. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (237 reviews)
"The owners were so kind and attentive, and the grounds are absolutely beautiful! Delicious food, gorgeous mountain air, and the horses were adorable. Thank you for having us!"
United States
Sinead
The price is S$311
includes taxes & fees
20 Oct - 21 Oct
The Dominion House Bed & Breakfast
A large, two-story house with a wrap-around porch and multiple chimneys.

2. Parkway House Goshen Family-Friendly Bed & Breakfast

Parkway House Goshen Family-Friendly Bed & Breakfast
3.0 star property
Goshen
10.0 out of 10, Exceptional, (37 reviews)
The price is S$312
includes taxes & fees
19 Oct - 20 Oct
Parkway House Goshen Family-Friendly Bed & Breakfast
A two-story house with a porch, a front door, and a small garden area with potted plants.

3. Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.4 out of 10, Exceptional, (191 reviews)
"What a quaint and charming bed and breakfast . The staff were readily available and so accommodating. I have already boomed another stay."
United States
Ruth
The price is S$185
includes taxes & fees
15 Oct - 16 Oct
Borland House Inn
A dining area with brick flooring, large arched windows, and outdoor seating visible through the windows.

4. 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 S$481
includes taxes & fees
5 Nov - 6 Nov
Stagecoach Inn
A modern bedroom with a four-poster bed, a desk, and a chair.

5. Columbus Hotel

Columbus Hotel
3.0 star property
Middletown
5.2 out of 10, (9 reviews)
"There is no front desk. All things considered this is not a $200+ hotel"
United States
Joseph
The price is S$262
includes taxes & fees
12 Oct - 13 Oct
Columbus Hotel
Exterior

6. Tin Brook Bed & Breakfast

Tin Brook Bed & Breakfast
3.0 star property
Walden
9.4 out of 10, Exceptional, (136 reviews)
"I stayed over the gift shop in the Strawberry Room and it was perfect!"
United States
Michael
The price is S$199
includes taxes & fees
13 Oct - 14 Oct
Tin Brook Bed & Breakfast
A two-story house with a red front door, a chimney, and a well-maintained lawn.

7. Villa Verde BB Greenwood Lake NY

Villa Verde BB Greenwood Lake NY
4.0 star property
Monroe
9.8 out of 10, Exceptional, (27 reviews)
The price is S$320
includes taxes & fees
20 Oct - 21 Oct
Villa Verde BB Greenwood Lake NY
A historic stone building with arched windows and ivy-covered walls.

8. The Castle at Skylands Manor

The Castle at Skylands Manor
3.5 star property
Ringwood
7.4 out of 10, Good, (396 reviews)
"Special thanks to Billy the innkeeper! He was great and made our stay very enjoyable! "
United States
Kyle
The price is S$250
includes taxes & fees
15 Oct - 16 Oct
The Castle at Skylands Manor
A brick building with a covered patio area featuring outdoor seating and string lights.

9. Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.4 out of 10, Exceptional, (109 reviews)
"The stay was wonderful. The personnel were very accommodating."
United States
Steven
The price is S$527
includes taxes & fees
15 Oct - 16 Oct
Cromwell Manor Inn
A small, single-story house with a steeply pitched roof, a front porch, and a staircase leading to the entrance.

10. Alpine Haus Bed & Breakfast Inn

Alpine Haus Bed & Breakfast Inn
2.0 star property
Vernon
9.2 out of 10, Wonderful, (343 reviews)
"the beds were very comfortable the breakfast was delicious"
United States
Debbie
The price is S$264
includes taxes & fees
18 Oct - 19 Oct
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

The Thayer Hotel at West Point

The Thayer Hotel at West Point

10/10 Excellent
"Incredible staff. Great location. Attention to guests superlative.West Point tours were fantastic. Only complaint was that it is extremely pricey. Which is understandable considering where we stayed. We ate there for 2 dinners, one lunch, and 1 breakfast. Meals are expensive but were great except for a breakfast that was stone-cold for $24 each."
Cameron 3-night trip
Posted 18 hours ago
The Thayer Hotel at West Point

Find out more about Chester

Chester B&B information

Number of reviews
1,267
Accommodation
12 B&B
Lowest Price
S$185
Highest Price
S$527

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. While you're enjoying your trip to Chester, you might want to explore the theatre scene by watching a show at Sugar Loaf Performing Arts Center.
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. Parkway House Goshen Family-Friendly Bed & Breakfast: 5 rooms. 3.6 mi (5.7 km) from the city centre. Enjoy the private garden and unique decor. Villa Verde BB Greenwood Lake NY: 2 rooms. Situated 9.1 mi (14.6 km) from the heart of Chester. Enjoy the free full breakfast and snack bar/deli. Borland House Inn: 5 rooms. 11.5 mi (18.5 km) from the city centre. Enjoy the free full breakfast and snack bar/deli. Tin Brook Bed & Breakfast: 6 rooms. Located 14.7 mi (23.7 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. If cultural attractions are high on your list, Museum Village and Sugar Loaf Performing Arts Center are spots to visit. You should put Castle Fun Center and The Rock Sports Complex 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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