7.3
Good
From $114
From $114
Info Categories
4-Star Hotel

Hotel with Free Wi-Fi

Hotel with Spa

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Berkshire Mountain Lodge
Lodge in Pittsfield MA
8.4
Very Good
From $178
From $178
Info Categories
Lodge with Free Wi-Fi

4-Star Lodge

Luxury Lodge

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19 more hotels nearby!
Berkshire Beauty-Full Home 4.3 mi from Pittsfield
Vacation Home in Richmond MA
10
Excellent
Info Categories
Vacation Home with Free Wi-Fi

4-Star Vacation Home

Dog Friendly Vacation Home

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Brook Farm Inn 6.1 mi from Pittsfield
Bed & Breakfast in Lenox MA
9.8
Excellent
From $180
From $180
Info Categories
Bed & Breakfast with Free Wi-Fi

4-Star Bed & Breakfast

Accessible Bed & Breakfast

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Disney Magic at Jiminy Mountain 8.2 mi from Pittsfield
Hotel in Hancock MA
9.6
Excellent
Info Categories
Hotel with Free Wi-Fi

4-Star Hotel

Hotel with Swimming Pool

Outdoor Pool  

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Shaker Mill Inn 9.0 mi from Pittsfield
Bed & Breakfast in West Stockbridge MA
9.4
Excellent
From $144
From $144
Info Categories
Bed & Breakfast with Free Wi-Fi

4-Star Bed & Breakfast

Boutique-style Bed & Breakfast

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Classic Stockbridge Cottage 11.5 mi from Pittsfield
Vacation Home in Stockbridge MA
Info Categories
Vacation Home with Free Wi-Fi

4-Star Vacation Home

Dog Friendly Vacation Home

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Stockbridge Country Inn 11.6 mi from Pittsfield
Bed & Breakfast in Stockbridge MA
9.4
Excellent
From $336
From $336
Info Categories
Bed & Breakfast with Free Wi-Fi

4-Star Bed & Breakfast

Bed & Breakfast for Adults Only

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Beautiful House In The Woods Huge Yard Hot Tub 14.2 mi from Pittsfield
Vacation Home in Great Barrington MA
Info Categories
Vacation Home with Free Wi-Fi

4-Star Vacation Home

Dog Friendly Vacation Home

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Mountain getaway in the Berkshires - walk to trails & town! 14.5 mi from Pittsfield
Vacation Home in Adams MA
10
Excellent
Info Categories
Vacation Home with Free Wi-Fi

4-Star Vacation Home

Vacation Home near Golf Courses

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Magical Country Retreat in the Berkshires 15.2 mi from Pittsfield
Vacation Home in Great Barrington MA
Info Categories
Vacation Home with Free Wi-Fi

4-Star Vacation Home

Family Friendly Vacation Home

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Berkshire Vacation Rentals: Beautiful Lakeside Cabin 15.7 mi from Pittsfield
Vacation Home in Becket MA
Info Categories
Vacation Home with Free Wi-Fi

4-Star Vacation Home

Vacation Home with Parking

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Woodland Hills Modern Cottage Minutes from Downtown Great Barrington 15.7 mi from Pittsfield
Vacation Home in Great Barrington MA
9.6
Excellent
Info Categories
Vacation Home with Free Wi-Fi

4-Star Vacation Home

Family Friendly Vacation Home

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East Rock Inn 17.3 mi from Pittsfield
Aparthotel in Great Barrington MA
Info Categories
Aparthotel with Free Wi-Fi

4-Star Aparthotel

Family Friendly Aparthotel

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Downtown Great Barrington Enjoy Mountain Views 17.6 mi from Pittsfield
Vacation Home in Great Barrington MA
9.0
Excellent
Info Categories
Vacation Home with Free Wi-Fi

4-Star Vacation Home

Dog Friendly Vacation Home

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Berkshire Vacation Rentals: Mountain View Estate Sleeps 18 18.4 mi from Pittsfield
Vacation Home in North Egremont MA
Info Categories
Vacation Home with Free Wi-Fi

4-Star Vacation Home

Dog Friendly Vacation Home

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The June Farms Lake House 18.7 mi from Pittsfield
Vacation Home in East Greenbush NY
Info Categories
Vacation Home with Free Wi-Fi

4-Star Vacation Home

Dog Friendly Vacation Home

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Berkshire Vacation Rentals: Private Estate Heated YEARROUND Outdoor Pool 18.8 mi from Pittsfield
Vacation Home in North Egremont MA
Info Categories
Vacation Home with Free Wi-Fi

4-Star Vacation Home

Dog Friendly Vacation Home

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Walk to college, theater festival, bike and walk paths 19.5 mi from Pittsfield
Vacation Home in Williamstown MA
3.0
Rated
Info Categories
Vacation Home with Free Wi-Fi

4-Star Vacation Home

Family Friendly Vacation Home

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The Egremont Village Inn 20.6 mi from Pittsfield
Inn in South Egremont MA
9.2
Excellent
From $126
From $126
Info Categories
Inn with Free Wi-Fi

4-Star Inn

Luxury Inn

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*Additional taxes or fees may apply. Please check the final price before completing your booking.
Categories:
  •     4 Star (21)
  •     Free Wi-Fi (21)
  •     Parking (17)
  •     Dog Friendly (14)
  •     Pool (8)
  •     Small (7)
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  •     Ski (6)
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  •     Family (5)
  •     Accessible (4)
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  •     Honeymoon (2)
  •     Indoor Pool (2)
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  •     Golf (2)
  •     Romantic (2)
  •     Sustainability Journey (1)
  •     Business (1)
  •     Boutique-Style (1)
  •     Spa (1)
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