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Check prices for these dates

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

Our top choices for Chester bed & breakfast

Exterior

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 ฿7,164
฿8,104 total
includes taxes & fees
24 Sept - 25 Sept
The Dominion House Bed & Breakfast
Exterior

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, (31 reviews)
"One of the best places we’ve stayed at, highly recommended!"
United States
Aakif
The price is ฿4,023
฿4,954 total
includes taxes & fees
22 Sept - 23 Sept
Parkway House Goshen Family-Friendly Bed & Breakfast
Exterior detail

3. 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 ฿3,621
฿4,406 total
includes taxes & fees
23 Sept - 24 Sept
Borland House Inn
Suite | Desk, iron/ironing board, free WiFi, individually decorated

4. 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 ฿3,465
฿6,370 total
includes taxes & fees
23 Sept - 24 Sept
Columbus Hotel
Exterior

5. 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 ฿4,582
฿5,183 total
includes taxes & fees
23 Sept - 24 Sept
Tin Brook Bed & Breakfast
Front of property

6. 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 ฿8,097
฿9,159 total
includes taxes & fees
22 Sept - 23 Sept
Villa Verde BB Greenwood Lake NY
Restaurant

7. 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 ฿12,453
฿15,334 total
includes taxes & fees
24 Sept - 25 Sept
Stagecoach Inn
Terrace/patio

8. 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 ฿10,871
฿12,841 total
includes taxes & fees
22 Sept - 23 Sept
Cromwell Manor Inn
Exterior

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 price is ฿6,331
฿7,402 total
includes taxes & fees
22 Oct - 23 Oct
The Castle at Skylands Manor
Miscellaneous

10. 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 ฿5,998
฿6,875 total
includes taxes & fees
23 Sept - 24 Sept
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

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

10/10 Excellent
"very comfy, and clean."
Alexandra 1-night trip
Posted less than an hour ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Find out more about Chester

Chester B&B information

Number of reviews
1,224
Accommodation
12 B&B
Lowest Price
฿4,406
Highest Price
฿15,334

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