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Check prices for these dates

Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov
In one month
20 Nov - 22 Nov
In two months
18 Dec - 20 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, (238 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 2.777.908 ₫
3.142.525 ₫ total
includes taxes & fees
9 Nov - 10 Nov
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, (41 reviews)
"One of the best places we’ve stayed at, highly recommended!"
United States
Aakif
The price is 4.155.233 ₫
5.116.132 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Parkway House Goshen Family-Friendly Bed & Breakfast
A dining area with brick flooring, large arched windows, and outdoor seating visible through the windows.

3. 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 7.875.045 ₫
9.696.319 ₫ total
includes taxes & fees
5 Nov - 6 Nov
Stagecoach Inn
A modern bedroom with a four-poster bed, a desk, and a chair.

4. Columbus Hotel

Columbus Hotel
3.0 star property
Middletown
5.0 out of 10, (12 reviews)
"Looks nothing like the pictures shown, a completely different room than what they advertise"
United States
Donald
The price is 3.566.058 ₫
5.934.226 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Columbus Hotel
Exterior

5. Tin Brook Bed & Breakfast

Tin Brook Bed & Breakfast
3.0 star property
Walden
9.4 out of 10, Exceptional, (140 reviews)
"I stayed over the gift shop in the Strawberry Room and it was perfect!"
United States
Michael
The price is 3.553.138 ₫
4.019.826 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Tin Brook Bed & Breakfast
A two-story house with a porch, a front door, and a small garden area with potted plants.

6. Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (197 reviews)
"Great location and nice sized room. Missed the en suite bathroom but was no problem. Breakfast was nice. Lovely town."
United States
William
The price is 3.343.050 ₫
4.067.632 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Borland House Inn
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, (28 reviews)
"Very nice B&B, with a very gracious host who served us a wonderful breakfast."
United States
Peter
The price is 6.279.363 ₫
7.103.531 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Villa Verde BB Greenwood Lake NY
A brick building with a covered patio area featuring outdoor seating and string lights.

8. Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.4 out of 10, Exceptional, (111 reviews)
"The stay was wonderful. The personnel were very accommodating."
United States
Steven
The price is 8.767.851 ₫
10.357.023 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Cromwell Manor Inn
A historic stone building with arched windows and ivy-covered walls.

9. 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 Castle at Skylands Manor
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, (345 reviews)
"the beds were very comfortable the breakfast was delicious"
United States
Debbie
The price is 4.651.380 ₫
5.331.645 ₫ total
includes taxes & fees
26 Oct - 27 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

Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

8/10 Good
"A perfectly fine cheap hotel. You get what you pay for. Rooms were fine, staff was very friendly. Felt safe and secure. Good location."
Joe 2-night trip
Posted 3 hours ago
Ramada by Wyndham Newburgh/West Point

Find out more about Chester

Chester B&B information

Number of reviews
1,328
Accommodation
12 B&B
Lowest Price
3.142.525 ₫
Highest Price
10.357.023 ₫

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.
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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