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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 €108
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, (40 reviews)
"One of the best places we’ve stayed at, highly recommended!"
United States
Aakif
The price is €253
includes taxes & fees
27 Oct - 28 Oct
Parkway House Goshen Family-Friendly Bed & Breakfast
A living room with a fireplace, a sectional sofa, and a chandelier.

3. 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.
Parkway House Goshen Bed & Breakfast Suite #3
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 €334
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
5.0 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 €178
includes taxes & fees
26 Oct - 27 Oct
Columbus Hotel
Exterior

6. 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 €139
includes taxes & fees
25 Oct - 26 Oct
Tin Brook Bed & Breakfast
A two-story house with a porch, a front door, and a small garden area with potted plants.

7. Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (196 reviews)
"Borland House was a pleasant stay. Clean, Friendly, Warm, Historic Feel, Comfortable Bri greeted us when we arrived and was extremely friendly and accommodating Bed was comfortable, room was cozy, very clean, water pressure is sufficient and the building itself gives off a warm and at home vibe. I highly recommend"
United States
Joseph
The price is €201
includes taxes & fees
26 Oct - 27 Oct
Borland House Inn
A large, white, multi-story house with a symmetrical design, featuring a central entrance and two side wings.

8. 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.
Parkway House Goshen Bed & Breakfast Suite #4
A two-story house with a red front door, a chimney, and a well-maintained lawn.

9. 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)
"Very nice B&B, with a very gracious host who served us a wonderful breakfast."
United States
Peter
The price is €245
includes taxes & fees
5 Nov - 6 Nov
Villa Verde BB Greenwood Lake NY
A large, white, two-story house with a wrap-around porch, multiple windows, and two prominent towers.

10. 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.
Parkway House Goshen Bed & Breakfast Suite #1
A large, two-story house with a wrap-around porch, a chimney, and a car parked in front.

11. Parkway House Goshen Bed & Breakfast Suite #2

Parkway House Goshen Bed & Breakfast Suite #2
Goshen
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, (110 reviews)
"The stay was wonderful. The personnel were very accommodating."
United States
Steven
The price is €357
includes taxes & fees
1 Nov - 2 Nov
Cromwell Manor Inn
A historic stone building with arched windows and ivy-covered walls.

13. 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 €198
includes taxes & fees
29 Oct - 30 Oct
The Castle at Skylands Manor
A bedroom with a wooden dresser, a mirror, a bed with a blue quilt, a window with blinds, and a wall-mounted light switch.

14. Twin Bedroom with Private Bathroom at Storm King Lodge

Twin Bedroom with Private Bathroom at Storm King Lodge
New Windsor
The price is €334
includes taxes & fees
21 Nov - 22 Nov
Twin Bedroom with Private Bathroom at Storm King Lodge
A bedroom with a bed, a window with curtains, a nightstand, and a chair.

15. Loft Room with Private Bathroom at Storm King Lodge

Loft Room with Private Bathroom at Storm King Lodge
New Windsor
The price is €334
includes taxes & fees
21 Nov - 22 Nov
Loft Room 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.

16. Alpine Haus Bed & Breakfast Inn

Alpine Haus Bed & Breakfast Inn
2.0 star property
Vernon
9.2 out of 10, Wonderful, (344 reviews)
"the beds were very comfortable the breakfast was delicious"
United States
Debbie
The price is €184
includes taxes & fees
25 Oct - 26 Oct
Alpine Haus Bed & Breakfast Inn
A sign for StormKing Lodge with a decorative flower and fox atop it, surrounded by greenery and a paved path.

17. Pine Suite with Private Bathroom at Storm King Lodge

Pine Suite with Private Bathroom at Storm King Lodge
New Windsor
The price is €391
includes taxes & fees
22 Nov - 23 Nov
Pine Suite with Private Bathroom at Storm King Lodge
A two-story house with a front porch, a stone chimney, and a well-maintained lawn.

18. Loft Suite with Private Bathroom at Storm King Lodge

Loft Suite with Private Bathroom at Storm King Lodge
New Windsor
The price is €403
includes taxes & fees
23 Oct - 24 Oct
Loft Suite with Private Bathroom at Storm King Lodge
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

Inn on the Hudson

Inn on the Hudson

8/10 Good
"Slightly dated hotel walkable into the town centre have used before and would use again"
Paul 1-night trip
Posted 17 hours ago
Inn on the Hudson

Find out more about Chester

Chester B&B information

Number of reviews
788
Accommodation
24 B&B
Lowest Price
€108
Highest Price
€403

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.