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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

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
9.6 out of 10, Exceptional, (240 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 AED 395
AED 447 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
9.8 out of 10, Exceptional, (46 reviews)
"One of the best places we’ve stayed at, highly recommended!"
United States
Aakif
The price is AED 486
AED 598 total
includes taxes & fees
5 Nov - 6 Nov
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
9.2 out of 10, Wonderful, (200 reviews)
"WONDERFUL!! Would absolutely stay here again. Super accommodating. Wonderful history. Absolutely stunning property!"
United States
Kimberly
The price is AED 376
AED 458 total
includes taxes & fees
5 Nov - 6 Nov
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 AED 1,119
AED 1,378 total
includes taxes & fees
5 Nov - 6 Nov
Stagecoach Inn
A living room with a fireplace, a sectional sofa, and a chandelier.

5. Parkway House Goshen Bed & Breakfast Suite #3

Parkway House Goshen Bed & Breakfast Suite #3
Goshen
10.0 out of 10, Exceptional, (1 review)
"Very comfortable place and Emily is a great host"
United States
James D.
The price is AED 607
AED 806 total
includes taxes & fees
5 Nov - 6 Nov
Parkway House Goshen Bed & Breakfast Suite #3
A modern bedroom with a four-poster bed, a desk, and a chair.

6. 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 AED 331
AED 644 total
includes taxes & fees
5 Nov - 6 Nov
Columbus Hotel
Exterior

7. Tin Brook Bed & Breakfast

Tin Brook Bed & Breakfast
3.0 star property
Walden
9.4 out of 10, Exceptional, (141 reviews)
"I stayed over the gift shop in the Strawberry Room and it was perfect!"
United States
Michael
The price is AED 505
AED 571 total
includes taxes & fees
5 Nov - 6 Nov
Tin Brook Bed & Breakfast
A two-story house with a red front door, a chimney, and a well-maintained lawn.

8. 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)
"Excellent fresh breakfast, very clean , gracious host"
United States
Mark
The price is AED 848
AED 959 total
includes taxes & fees
5 Dec - 6 Dec
Villa Verde BB Greenwood Lake NY
A large, white, two-story house with a wrap-around porch, multiple windows, and two prominent towers.

9. Parkway House Goshen Bed & Breakfast Suite #1

Parkway House Goshen Bed & Breakfast Suite #1
Goshen
10.0 out of 10, Exceptional, (1 review)
"Had a great stay with my family while visiting Legoland. Emily and her family were very accommodating. Her guest first approach was felt. Room was great, perfect for my large family. Excellent location as well, walking distance to downtown Goshen. 5 minute drive to Legoland. Definitely going to stay there again!"
United States
Kam K.
The price is AED 628
AED 837 total
includes taxes & fees
5 Nov - 6 Nov
Parkway House Goshen Bed & Breakfast Suite #1
A large, white, multi-story house with a symmetrical design, featuring a central entrance and two side wings.

10. Parkway House Goshen Bed & Breakfast Suite #4

Parkway House Goshen Bed & Breakfast Suite #4
Goshen
10.0 out of 10, Exceptional, (2 reviews)
"Great stay. Close to everything downtown. Check in was smooth and easy. Would absolutely stay again. "
United States
Michael F.
The price is AED 586
AED 781 total
includes taxes & fees
5 Nov - 6 Nov
Parkway House Goshen Bed & Breakfast Suite #4
A large, two-story house with a wrap-around porch and two towers.

11. Parkway House Goshen Bed & Breakfast Suite #2

Parkway House Goshen Bed & Breakfast Suite #2
Goshen
The price is AED 1,466
AED 1,945 total
includes taxes & fees
8 Nov - 9 Nov
Parkway House Goshen Bed & Breakfast Suite #2
A brick building with a covered patio area featuring outdoor seating and string lights.

12. Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.4 out of 10, Exceptional, (112 reviews)
"This property was beautiful!! Everything was clean and thoughtful, breakfast was homemade, with options from the staff. Staff were lovely, so friendly. Roy, the golden retriever was a cutie!! :)"
United States
Alice
The price is AED 1,142
AED 1,349 total
includes taxes & fees
5 Nov - 6 Nov
Cromwell Manor Inn
A two-story house with a front porch, a stone chimney, and a well-maintained lawn.

13. Twin Bedroom with Private Bathroom at Storm King Lodge

Twin Bedroom with Private Bathroom at Storm King Lodge
New Windsor
The price is AED 1,056
AED 1,291 total
includes taxes & fees
8 Nov - 9 Nov
Twin Bedroom with Private Bathroom at Storm King Lodge
A two-story house with a front porch, a stone chimney, and a well-maintained lawn.

14. Loft Room with Private Bathroom at Storm King Lodge

Loft Room with Private Bathroom at Storm King Lodge
New Windsor
The price is AED 1,056
AED 1,291 total
includes taxes & fees
8 Nov - 9 Nov
Loft Room with Private Bathroom at Storm King Lodge
A spacious room with a grand piano, wooden ceiling beams, and a cozy seating area with chairs and a sofa.

15. Loft Suite with Private Bathroom at Storm King Lodge

Loft Suite with Private Bathroom at Storm King Lodge
New Windsor
The price is AED 1,267
AED 1,552 total
includes taxes & fees
8 Nov - 9 Nov
Loft Suite with Private Bathroom at Storm King Lodge
A wooden-paneled room with a bed, a chair, a dresser, and a window with curtains.

16. Pine Suite with Private Bathroom at Storm King Lodge

Pine Suite with Private Bathroom at Storm King Lodge
New Windsor
The price is AED 1,267
AED 1,552 total
includes taxes & fees
8 Nov - 9 Nov
Pine Suite with Private Bathroom at Storm King Lodge
A small, single-story house with a steeply pitched roof, a front porch, and a staircase leading to the entrance.

17. Alpine Haus Bed & Breakfast Inn

Alpine Haus Bed & Breakfast Inn
2.0 star property
Vernon
9.2 out of 10, Wonderful, (346 reviews)
"the beds were very comfortable the breakfast was delicious"
United States
Debbie
The price is AED 735
AED 842 total
includes taxes & fees
5 Nov - 6 Nov
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

Studio 6 Extended Stay Fishkill Westage Center NY

Studio 6 Extended Stay Fishkill Westage Center NY

8/10 Good
"Good job"
Salah 2-night trip
Posted 1 day ago
Studio 6 Extended Stay Fishkill Westage Center NY

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. While you're enjoying your trip to Chester, you might want to explore the theater scene by catching a show at Sugar Loaf Performing Arts Center.
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. Parkway House Goshen Family-Friendly Bed & Breakfast: 5 rooms. 3.6 mi (5.7 km) from the downtown core. Enjoy the private yard and unique décor. 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 deli. Borland House Inn: 5 rooms. 11.5 mi (18.5 km) from the heart of downtown. Enjoy the free full breakfast and 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 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. If cultural attractions are high on your list, Museum Village and Sugar Loaf Performing Arts Center are spots to check out. You might 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?
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.

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