Top Bed and Breakfasts in The Berkshires

Find the Top Bed and Breakfasts in The Berkshires – 20+ Quality Options from Leading Providers

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22 Guests, 1 Room
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1-20 out of 21 bed and breakfasts
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Bed & Breakfast
8.6
Great40 reviews
From   US$ 161 /nightSelect
  • Historic home with luxurious accommodations
  • On-site dining by Executive Chef Jeremy Berlin
  • Private en-suite bathrooms in all rooms
8.4
Great82 reviews
From   US$ 129 /nightSelect
  • Gourmet breakfast with specialty coffees
  • Designer rooms with private balconies
  • Private deck next to koi pond
Bed & Breakfast
8.0
Great39 reviews
  • Private baths
  • On-site dining
  • Ski storage
From   US$ 171 /nightSelect
  • Home-cooked breakfast served daily
  • Historical bed and breakfast charm
  • Wrap-around porches with great views
Bed & Breakfast
8.6
Great19 reviews
  • Heated Pool
  • Fitness Center
  • Wine Lounge
From   US$ 354 /nightSelect
  • Gourmet breakfast with unique daily offerings
  • Three distinct pet-friendly lodging options
  • Wine and cheese social hour
Bed & Breakfast
8.4
Great49 reviews
  • Outdoor pool
  • Wine bar
  • Hiking trails
From   US$ 319 /nightSelect
  • Unique elopement packages with planning assistance
  • Gourmet farm-to-table breakfast served daily
  • Scenic grounds for outdoor activities
Bed & Breakfast
8.4
Great56 reviews
  • Private Patios
  • In-Room Breakfast
  • Gas Fireplaces
From   US$ 358 /nightSelect
  • In-room breakfast with homemade and fresh options
  • Private entrances and outdoor patios for rooms
  • Pet-friendly accommodations with thoughtful amenities
Bed & Breakfast
8.2
Great79 reviews
  • Jetted Tubs
  • Fireplaces
  • Breakfast Delivery
From   US$ 400 /nightSelect
  • Elegant rooms with working fireplaces
  • Private jetted tubs for ultimate relaxation
  • In-room breakfast delivered to your suite
Bed & Breakfast
8.6
Great39 reviews
  • Music Room
  • Outdoor Pool
  • Pet-Friendly
From   US$ 253 /nightSelect
  • Historic mansion with unique charm
  • Exceptional breakfast with local ingredients
  • Music room with various instruments
Bed & Breakfast
8.4
Great65 reviews
  • Family Rooms
  • Private Bathroom
  • Free Parking
From   US$ 200 /nightSelect
  • Family rooms available for all ages
  • Air-conditioned rooms for comfort
  • Free parking on the property
Bed & Breakfast
8.6
Great36 reviews
  • Gourmet Breakfast
  • Wine Hour
  • Charming Rooms
From   US$ 336 /nightSelect
  • Gourmet three-course breakfast experience
  • Daily wine and cheese social hour
  • Charming historic decor throughout inn
8.2
Great62 reviews
  • Gourmet Breakfast
  • Cozy Library
  • Beautiful Gardens
From   US$ 109 /nightSelect
  • Gourmet breakfast with unique homemade dishes
  • Historic charm with modern decor elements
  • Pet-friendly accommodations with special amenities
Bed & Breakfast
8.4
Great39 reviews
  • Beautiful gardens
  • Library
  • Picnic area
From   US$ 272 /nightSelect
  • Historic charm with Victorian decor
  • Delicious homemade breakfast options
  • Engaging storytelling by welcoming hosts
8.6
Great55 reviews
  • Heated Pool
  • Garden Views
  • Chef's Pantry
From   US$ 459 /nightSelect
  • Multi-course gourmet breakfast daily
  • Adults-only serene atmosphere
  • Beautifully appointed historic rooms
Bed & Breakfast
8.4
Great57 reviews
  • Gourmet Breakfast
  • Themed Rooms
  • Common Area Games
From   US$ 171 /nightSelect
  • Historical significance with famous past guests
  • Chef-crafted gourmet breakfasts daily
  • Themed rooms inspired by local history
8.6
Great39 reviews
  • Outdoor firepit
  • Steam shower
  • Spa tub
From   US$ 332 /nightSelect
  • Artist-decorated boutique inn
  • Organic materials and locally-sourced amenities
  • Views of Ashuwillticook Rail Trail
Bed & Breakfast
8.4
Great32 reviews
  • Outdoor pool
  • Library
  • Fireplace
From   US$ 261 /nightSelect
  • Gourmet chef-prepared breakfast daily
  • Charming Victorian décor with modern comforts
  • Heated outdoor pool for summer relaxation
Bed & Breakfast
7.8
Very good36 reviews
  • Hot tub
  • Outdoor fireplace
  • Ski storage
From   US$ 125 /nightSelect
  • On-site spa and wellness centre
  • Mountain views with outdoor dining
  • Indoor play area for children
Bed & Breakfast
8.4
Great6 reviews
  • Gourmet Breakfast
  • Beautiful Gardens
  • Romantic Rooms
From   US$ 273 /nightSelect
  • Gourmet breakfast with seasonal cuisine
  • Romantic rooms with tailored decor
  • Lovely gardens for relaxation
Bed & Breakfast
  • Game Room
  • Private Parking
  • Picnic Area
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  • Garden-view accommodations
  • On-site game room
  • American breakfast options
Bed & Breakfast
8.0
Great8 reviews
  • On-site Spa
  • Swimming Pool
  • Breakfast Provided
From   US$ 189 /nightSelect
  • Relaxing on-site spa experience
  • Inviting swimming pool area
  • Complimentary breakfast provided daily
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