Top Resorts in The Berkshires

Find the Top Resorts in The Berkshires – 50+ Quality Options from Leading Providers

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Rooms & Guests
22 Guests, 1 Room
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41-52 out of 52 resorts
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Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
8.4
Great108 reviews
From   US$ 85 /nightSelect
  • Dog-friendly policy for traveling pets
  • Diverse breakfast options exceeding expectations
  • Whirlpool tub available in King suite
8.4
Great52 reviews
From   US$ 110 /nightSelect
  • Spacious suites with full kitchens
  • Pet-friendly accommodations for travelers
  • Central location near local attractions
8.6
Great40 reviews
  • King Suites
  • Whirlpool Tubs
  • Private Balconies
From   US$ 275 /nightSelect
  • Historic property with antique decor
  • Customized dining with local ingredients
  • Private balconies in select suites
Inn
8.2
Great22 reviews
  • On-site Spa
  • Dog-Friendly Rooms
  • Event Hosting
From   US$ 614 /nightSelect
  • Hästens handmade luxury mattresses
  • Artfully designed themed guest rooms
  • Homemade gourmet breakfast included
7.2
Very good12 reviews
  • Shared kitchen
  • Concierge service
  • Air conditioning
From   US$ 51 /nightSelect
  • Shared kitchen for guest convenience
  • Fishing activities nearby for guests
  • Pets allowed for friendly stays
8.6
Great61 reviews
  • Local Cuisine
  • Live Music
  • Pet Amenities
From   US$ 179 /nightSelect
  • Unique historical character and industrial design
  • Exceptional dining with local ingredients onsite
  • Pet-friendly with thoughtful dog amenities
Bed & Breakfast
8.6
Great40 reviews
  • Private bathrooms
  • On-site restaurant
  • Gas fireplaces
From   US$ 161 /nightSelect
  • Boutique bed & breakfast in historic building
  • Private en-suite bathrooms in all rooms
  • On-site restaurant by Executive Chef
8.4
Great51 reviews
  • Jacuzzi suites
  • Large lawn
  • Kitchenettes
From   US$ 148 /nightSelect
  • Beautiful scenic location by Housatonic River
  • Jacuzzi suites for added comfort
  • Large private lawn for relaxation
8.6
Great55 reviews
  • Heated Pool
  • Chef's Pantry
  • Homemade Breakfast
From   US$ 459 /nightSelect
  • Gourmet farm-to-table breakfast experience
  • Walking distance to cultural attractions
  • Beautifully maintained grounds and gardens
8.4
Great79 reviews
  • Indoor Pool
  • Fitness Centre
  • Pet-Friendly
From   US$ 110 /nightSelect
  • Scenic pond views for relaxation
  • Complimentary cookies in the lobby
  • Free laundry service for guests
8.6
Great68 reviews
  • Heated pool
  • Fitness center
  • Game room
From   US$ 199 /nightSelect
  • On-site art exhibitions
  • Heated outdoor swimming pool
  • Fitness center with sauna
8.2
Great60 reviews
  • Adventure Park
  • Heated Pool
  • Ski Access
From   US$ 189 /nightSelect
  • Ski-in/ski-out access to Jiminy Peak
  • Outdoor heated pool for year-round use
  • On-site adventure park attractions