Bed and breakfast vacation rentals in Berkshire County
Find and book unique bed and breakfast rentals on Airbnb
Top-rated bed and breakfast rentals in Berkshire County
Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Berkshire County bed and breakfast rentals
Family-friendly bed and breakfast rentals
Room in Becket
Canterbury Farm
Sep 15 – 22
Room in Williamstown
4.83 out of 5 average rating, 388 reviewsA Beautiful Home & Gardens In The Berkshires
Nov 7 – 14
Room in Pittsfield
4.99 out of 5 average rating, 376 reviewsLarge guest suite w/private bath in the Berkshires
Apr 13 – 20
Room in Williamstown
4.95 out of 5 average rating, 106 reviewsCozy 3 bedroom cape at end of road in Williamstown
Nov 17 – 24
Room in Lenox
4.75 out of 5 average rating, 4 reviewsQUEEN ROOM Bed&Breakfast private bath
Sep 9 – 16
Bed and breakfast rentals with breakfast
Room in New Marlborough
5.0 out of 5 average rating, 14 reviewsThe Inn at Freeman Elms Farm B&B- Harriot's Room
Jun 26 – Jul 3
Room in Lenox
5.0 out of 5 average rating, 3 reviewsRoom 7: Leighton Rollins Room - Apple Tree Inn
Nov 11 – 18
Room in Lenox
Modern Apt w/Kitchen in a Classic Bed & Breakfast
Oct 21 – 28
Nature lodge in Sheffield
4.93 out of 5 average rating, 68 reviewsSheffield Lodge - Monument Room
Jun 5 – 12
Nature lodge in Sheffield
5.0 out of 5 average rating, 14 reviewsSheffield Lodge
Jan 17 – 24
Nature lodge in Sheffield
4.92 out of 5 average rating, 39 reviewsSheffield Lodge - Washington Room
Jun 21 – 28
Nature lodge in Sheffield
4.93 out of 5 average rating, 67 reviewsSheffield Lodge - Greylock Room
Nov 11 – 18
Nature lodge in Sheffield
4.97 out of 5 average rating, 66 reviewsSheffield Lodge - Everett Room
Sep 6 – 13
Bed and breakfast rentals with a patio
Room in Pittsfield
Duchess of Pomeroy Queen Bed
Dec 10 – 17
Bed and breakfast in Cheshire
Field of Dreams-Harbour House Inn
Mar 4 – 11
Cottage in Williamstown
4.97 out of 5 average rating, 72 reviewsArtistic Nature Cottage
Apr 14 – 21
Cabin in West Stockbridge
4.98 out of 5 average rating, 48 reviewsModern Cabin near Tanglewood
Sep 27 – Oct 4
Room in Becket
Canterbury Farm
Sep 15 – 22
Destinations to explore
- Rentals with breakfast United States
- Bed and breakfasts United States
- Bed and breakfasts New York
- Rentals with breakfast New York
- Rentals with breakfast Massachusetts
- Bed and breakfasts Massachusetts
- Rentals with breakfast Massachusetts
- Bed and breakfasts Massachusetts
- Chalet rentals Berkshire County
- Apartment rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Condo rentals Berkshire County
- Kid-friendly rentals Berkshire County
- Rentals with beach access Berkshire County
- Cottage rentals Berkshire County
- Monthly Rentals Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Rentals with lake access Berkshire County
- Fitness-friendly rentals Berkshire County
- Rentals with pools Berkshire County
- Rentals with outdoor seating Berkshire County
- Beachfront rentals Berkshire County
- Farmstay rentals Berkshire County
- Rentals with a fire pit Berkshire County
- Rentals with a washer and dryer Berkshire County
- Rentals with a kayak Berkshire County
- Rentals with a sauna Berkshire County
- Rentals with breakfast Berkshire County
- Rentals with a fireplace Berkshire County
- Hotel rentals Berkshire County
- Boutique hotel rentals Berkshire County
- Guesthouse rentals Berkshire County
- Rentals with an EV charger Berkshire County
- House rentals Berkshire County
- Pet-friendly rentals Berkshire County
- Private suite rentals Berkshire County
- Family-friendly rentals Berkshire County
- Cabin rentals Berkshire County
- Waterfront rentals Berkshire County
- Rentals with a patio Berkshire County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom