Lodging Image

Find Chester Bed And Breakfast

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

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 ￥33,822
￥38,261 total
includes taxes & fees
Oct 1 - Oct 2
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, (32 reviews)
"One of the best places we’ve stayed at, highly recommended!"
United States
Aakif
The price is ￥18,045
￥22,218 total
includes taxes & fees
Sep 24 - Sep 25
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 ￥50,929
￥62,707 total
includes taxes & fees
Sep 24 - Sep 25
Stagecoach Inn
A two-story house with a porch, a front door, and a small garden area with potted plants.

4. Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.4 out of 10, Exceptional, (186 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 ￥17,110
￥20,818 total
includes taxes & fees
Sep 27 - Sep 28
Borland House Inn
A two-story house with a red front door, a chimney, and a well-maintained lawn.

5. 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 ￥37,844
￥42,811 total
includes taxes & fees
Sep 24 - Sep 25
Villa Verde BB Greenwood Lake NY
A large, white, multi-story house with a symmetrical design, featuring a central entrance and two side wings.

6. 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 ￥26,249
￥36,403 total
includes taxes & fees
Sep 24 - Sep 25
Parkway House Goshen Bed & Breakfast Suite #4
A modern bedroom with a four-poster bed, a desk, and a chair.

7. 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 ￥16,649
￥30,400 total
includes taxes & fees
Sep 27 - Sep 28
Columbus Hotel
A small, single-story house with a steeply pitched roof, a front porch, and a staircase leading to the entrance.

8. Alpine Haus Bed & Breakfast Inn

Alpine Haus Bed & Breakfast Inn
2.0 star property
Vernon
9.2 out of 10, Wonderful, (340 reviews)
"the beds were very comfortable the breakfast was delicious"
United States
Debbie
The price is ￥26,051
￥29,861 total
includes taxes & fees
Oct 4 - Oct 5
Alpine Haus Bed & Breakfast Inn
A living room with a fireplace, a sectional sofa, and a chandelier.

9. 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 ￥24,499
￥33,875 total
includes taxes & fees
Sep 24 - Sep 25
Parkway House Goshen Bed & Breakfast Suite #3
A brick building with a covered patio area featuring outdoor seating and string lights.

10. 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 ￥51,323
￥60,627 total
includes taxes & fees
Sep 24 - Sep 25
Cromwell Manor Inn
A historic stone building with arched windows and ivy-covered walls.

11. 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 ￥26,113
￥30,730 total
includes taxes & fees
Oct 15 - Oct 16
The Castle at Skylands Manor
A large, two-story house with a wrap-around porch, a chimney, and a car parked in front.

12. Parkway House Goshen Bed & Breakfast Suite #2

Parkway House Goshen Bed & Breakfast Suite #2
Goshen
The price is ￥46,373
￥62,013 total
includes taxes & fees
Sep 29 - Sep 30
Parkway House Goshen Bed & Breakfast Suite #2
A large, white, two-story house with a wrap-around porch, multiple windows, and two prominent towers.

13. Parkway House Goshen Bed & Breakfast Suite #1

Parkway House Goshen Bed & Breakfast Suite #1
Goshen
The price is ￥39,373
￥54,410 total
includes taxes & fees
Sep 27 - Sep 28
Parkway House Goshen Bed & Breakfast Suite #1
A wooden-paneled room with a fireplace, a world map, a fire extinguisher, and a vintage suitcase.

14. Pine Suite with Private Bath at Storm King Lodge

Pine Suite with Private Bath at Storm King Lodge
New Windsor
The price is ￥54,272
￥67,409 total
includes taxes & fees
Sep 27 - Sep 28
Pine Suite with Private Bath at Storm King Lodge
A bedroom with a bed, a window with curtains, a nightstand, and a chair.

15. Loft Room with Private Bath at Storm King Lodge

Loft Room with Private Bath at Storm King Lodge
New Windsor
The price is ￥45,227
￥56,237 total
includes taxes & fees
Sep 27 - Sep 28
Loft Room with Private Bath at Storm King Lodge
A two-story house with a front porch, a stone chimney, and a well-maintained lawn.

16. Twin Bedroom with Private Bath at Storm King Lodge

Twin Bedroom with Private Bath at Storm King Lodge
New Windsor
The price is ￥36,181
￥44,879 total
includes taxes & fees
Sep 27 - Sep 28
Twin Bedroom with Private Bath at Storm King Lodge
A room with a wooden floor, a dresser, two leather armchairs, a small table with a clock, a lamp, and a framed picture on the wall.

17. Loft Suite with Private Bath at Storm King Lodge

Loft Suite with Private Bath at Storm King Lodge
New Windsor
The price is ￥54,272
￥67,409 total
includes taxes & fees
Sep 27 - Sep 28
Loft Suite with Private Bath at Storm King Lodge

18. Tin Brook Bed & Breakfast

Tin Brook Bed & Breakfast
3.0 star property
Walden
9.4 out of 10, Exceptional, (133 reviews)
"I had a wonderful stay at the Tin Brook B&B. The owner, David is wonderful, accommodating and a great host. My daughter and I loved the room we were in. We loved the location. All around great stay."
United States
Andrea
The price is ￥21,630
￥24,471 total
includes taxes & fees
Sep 24 - Sep 25
Tin Brook Bed & Breakfast
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah

10/10 Excellent
"Very clean rooms, everything was wonderful—staff, breakfast, everything!"
Howard 1-night trip
Posted 3 hours ago
Hampton Inn & Suites Mahwah

Find out more about Chester

Chester B&B information

Number of reviews
1,224
Accommodation
17 B&B
Lowest Price
￥20,818
Highest Price
￥62,707

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. Columbus Hotel: 15 rooms. Located 9.5 mi (15.3 km) from the core of Chester. Enjoy the unique décor and bar/lounge.
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.

Explore a world of travel with Expedia