List your B&B
Manage your B&B
B&B Chester
97 Bed and Breakfasts
in and around
Chester
City
(
Massachusetts
,
United States
)
Filter
Sort
Our top selection
Price: Low → High
Price: High → Low
Best rated
Map
Accommodation type
Holiday home
Apartment
Bed & breakfast
Inn
Pension
Small-scale hotel
Review score
General amenities
Free Wifi
Electric vehicle charging station
Garden
Pets allowed
Free parking
Swimming pool
More
Room Amenities
Private bathroom
Family room
Private entrance
Air conditioning
Bath
Private terrace
More
Accessibility
Wheelchair accessible
Entire unit located on ground floor
Adults only
Accommodations just outside your destination
Near Chester
Spacious Retreat near Tanglewood & Ski Resorts
Housatonic
8
Direct reservation
(32.3 km from Chester)
Shaker Mill Inn
West Stockbridge
9.2
Direct reservation
(32.8 km from Chester)
Downtown Great Barrington Enjoy Mountain Views
Great Barrington
10
Direct reservation
(33.1 km from Chester)
The Berkshire Mountain Inn
Great Barrington
9.5
Direct reservation
(33.4 km from Chester)
Daniel Stebbins B and B
South Hadley
9.6
Direct reservation
(33.5 km from Chester)
Cozy First Floor Apartment
Chicopee
9.7
Direct reservation
(33.6 km from Chester)
Summer and Fall in Sheffield with Monthly Special Pricing Available
Sheffield
10
Direct reservation
(33.7 km from Chester)
Beautiful House in the Woods, Huge Yard, Hot Tub
Great Barrington
10
Direct reservation
(33.7 km from Chester)
Great Barrington Lakeside Getaway w/ Kayak & Grill
Great Barrington
9.3
Direct reservation
(33.9 km from Chester)
Peaceful Meadow Retreat
Granby
9.3
Direct reservation
(34.1 km from Chester)
The Inn at Richmond
Richmond
9.2
Direct reservation
(34.2 km from Chester)
1 Mi to Vineyard: Serene Berkshires Country Escape
Richmond
10
Direct reservation
(34.4 km from Chester)
Private Mountain Retreat On 10 Acres The Perfect Family Escape
Cheshire
10
Direct reservation
(35.1 km from Chester)
Lake Congamond Suffield House
Granby
9
Direct reservation
(35.1 km from Chester)
2 Mi to Downtown: Springfield Apt w/ Balcony!
Springfield
8.6
Direct reservation
(35.3 km from Chester)
Mountain Biking Hub: 5 Mi to Berkshire East!
Hawley
9
Direct reservation
(35.4 km from Chester)
Naomi's Inn Bed & Breakfast
Springfield
8.9
Direct reservation
(35.4 km from Chester)
Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!
Hawley
10
Direct reservation
(35.5 km from Chester)
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Hawley
10
Direct reservation
(35.8 km from Chester)
Secluded Family Getaway w/ On-Site Creek in Hawley
Hawley
9
Direct reservation
(35.8 km from Chester)
Harbour House Inn B&B
Cheshire
9.6
Direct reservation
(36.1 km from Chester)
Lakefront Granby Escape w/ Private Dock & Kayaks!
Granby
9.5
Direct reservation
(36.1 km from Chester)
Lily's Lodge
West Springfield
8.4
Direct reservation
(36.1 km from Chester)
Wilder House Berkshires
Sheffield
9.5
Direct reservation
(36.6 km from Chester)
Load next page
1
2
3
4
5
