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Our top choices for Chester bed & breakfast

1. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.6 out of 10, Exceptional, (241 reviews)
"Amazing! The historic home sits on 40 acres of beautiful land inviting all guests to sit back and unwind. The beautiful home is decorated exquisitely and the hosts are warm and welcoming. If you are visiting West Point this place is a short drive away. It is nestled in a beautiful area making it an excellent option for a weekend get away-whether you are going to watch an Army football game or just want to get away, you will not be disappointed."
United States
Sally
The price is HK$1,687
HK$1,908 total
includes taxes & fees
18 Nov - 19 Nov
The Dominion House Bed & Breakfast

2. Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (201 reviews)
"WONDERFUL!! Would absolutely stay here again. Super accommodating. Wonderful history. Absolutely stunning property!"
United States
Kimberly
The price is HK$804
HK$978 total
includes taxes & fees
16 Nov - 17 Nov
Borland House Inn

3. 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 HK$667
HK$1,331 total
includes taxes & fees
16 Nov - 17 Nov
Columbus Hotel

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 HK$2,269
HK$2,794 total
includes taxes & fees
20 Nov - 21 Nov
Stagecoach Inn

5. Tin Brook Bed & Breakfast

Tin Brook Bed & Breakfast
3.0 star property
Walden
9.4 out of 10, Exceptional, (142 reviews)
"I stayed over the gift shop in the Strawberry Room and it was perfect!"
United States
Michael
The price is HK$1,079
HK$1,220 total
includes taxes & fees
16 Nov - 17 Nov
Tin Brook Bed & Breakfast

6. 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 HK$1,906
HK$2,157 total
includes taxes & fees
16 Nov - 17 Nov
Villa Verde BB Greenwood Lake NY

7. Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.6 out of 10, Exceptional, (114 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 HK$1,779
HK$2,101 total
includes taxes & fees
16 Nov - 17 Nov
Cromwell Manor Inn

8. The Castle at Skylands Manor

The Castle at Skylands Manor
3.5 star property
Ringwood
7.6 out of 10, Good, (398 reviews)
"Special thanks to Billy the innkeeper! He was great and made our stay very enjoyable! "
United States
Kyle
The price is HK$2,707
HK$3,100 total
includes taxes & fees
21 Nov - 22 Nov
The Castle at Skylands Manor

9. Loft Room with Private Bathroom at Storm King Lodge

Loft Room with Private Bathroom at Storm King Lodge
New Windsor
The price is HK$2,256
HK$2,656 total
includes taxes & fees
16 Nov - 17 Nov
Loft Room with Private Bathroom at Storm King Lodge

10. Twin Bedroom with Private Bathroom at Storm King Lodge

Twin Bedroom with Private Bathroom at Storm King Lodge
New Windsor
The price is HK$2,256
HK$2,656 total
includes taxes & fees
16 Nov - 17 Nov
Twin Bedroom with Private Bathroom at Storm King Lodge

11. Loft Suite with Private Bathroom at Storm King Lodge

Loft Suite with Private Bathroom at Storm King Lodge
New Windsor
The price is HK$2,707
HK$3,186 total
includes taxes & fees
16 Nov - 17 Nov
Loft Suite with Private Bathroom at Storm King Lodge

12. Pine Suite with Private Bathroom at Storm King Lodge

Pine Suite with Private Bathroom at Storm King Lodge
New Windsor
The price is HK$2,707
HK$3,186 total
includes taxes & fees
16 Nov - 17 Nov
Pine Suite with Private Bathroom at Storm King Lodge

13. 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, (50 reviews)
"One of the best places we’ve stayed at, highly recommended!"
United States
Aakif
The price is HK$1,086
HK$1,337 total
includes taxes & fees
16 Nov - 17 Nov
Parkway House Goshen Family-Friendly Bed & Breakfast

14. 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 HK$1,569
HK$1,799 total
includes taxes & fees
16 Nov - 17 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.

Learn more about Chester

Lace up your hiking boots and hit the trails at Goosepond Mountain State Park for stunning views. After working up an appetite, head to Castle Fun Centre for go-karts, mini-golf, and arcade games.

A bridge with a plaque reading "City of Chester Queens Park Bridge 1923".

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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