Berkshire Inn
Motel in Pittsfield MA
7.3
Good
From $89
From $89
Info Categories
Motel with Parking


Motel near Ski Resorts


Motel with Swimming Pool

Outdoor Pool  


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The Central Downtown Inn Suites
Hotel in Pittsfield MA
9.1
Excellent
From $136
From $136
Info Categories
Hotel with Parking


Luxury Hotel


Hotel near Golf Courses


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Berkshire Mountain Lodge
Lodge in Pittsfield MA
8.4
Very Good
From $178
From $178
Info Categories
Lodge with Parking


Luxury Lodge


Lodge near Ski Resorts


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Hotel on North
Hotel in Pittsfield MA
10
Excellent
From $322
From $322
Info Categories
Hotel with Parking


Hotel with Rooms With Fireplace


Boutique-style Hotel


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Fairbridge Inn Express Pittsfield
Hotel in Pittsfield MA
4.3
Rated
From $77
From $77
Info Categories
Hotel with Parking


Hotel near Ski Resorts


Hotel with Free Wi-Fi


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Berkshire Vacation Rentals: Chic Pittsfield Home With A View
Vacation Home in Pittsfield MA
Info Categories
Vacation Home with Parking


Dog Friendly Vacation Home


Vacation Home with Free Wi-Fi


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Dalton Vacation Rental Near Hiking and Skiing!
Vacation Home in Pittsfield MA
Info Categories
Vacation Home with Parking


Vacation Home with Free Wi-Fi


3-Star Vacation Home


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Cozy Dalton Studio with Porch and Outdoor Seating!
Apartment in Pittsfield MA
Info Categories
Apartment with Parking


Apartment with Free Wi-Fi


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Pittsfield Home with Deck - 12 Mi to Jiminy Peak!
Vacation Home in Pittsfield MA
Info Categories
Vacation Home with Parking


Vacation Home with Free Wi-Fi


3-Star Vacation Home


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Downtown Pittsfield Vacation Rental Near Hiking!
Apartment in Pittsfield MA
Info Categories
Apartment with Parking


Apartment with Free Wi-Fi


3-Star Apartment


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Cute Cape Cod Style Home
Vacation Home in Pittsfield MA
5.7
Rated
Info Categories
Vacation Home with Parking


Family Friendly Vacation Home


Vacation Home with Free Wi-Fi


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Heart of the Berkshires Motel
Motel in Pittsfield MA
6.6
Rated
From $82
From $82
Info Categories
Motel with Parking


Motel Taking Steps Towards Sustainability


Dog Friendly Motel


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Spacious Historic Home in the Berkshires!
Vacation Home in Pittsfield MA
Info Categories
Vacation Home with Parking


Vacation Home with Free Wi-Fi


3-Star Vacation Home


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281 more hotels nearby!
Lenox House with Screened Patio and Mountain View 2.9 mi from Pittsfield
Vacation Home in Lenox MA
Info Categories
Vacation Home with Parking


Dog Friendly Vacation Home


Vacation Home with Swimming Pool

Outdoor Pool  


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Charming Lenox Home View of October Mountain 2.9 mi from Pittsfield
Vacation Home in Lenox MA
Info Categories
Vacation Home with Parking


Dog Friendly Vacation Home


Vacation Home with Swimming Pool

Outdoor Pool  


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Huge 3 bdrm Designer House in Lenox 3.0 mi from Pittsfield
Vacation Home in Lenox MA
Info Categories
Vacation Home with Parking


Vacation Home near Ski Resorts


Vacation Home with Swimming Pool

Private Pool    Outdoor Pool  


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Life House, Berkshires 3.7 mi from Pittsfield
Hotel in Lenox MA
8.0
Very Good
From $123
From $123
Info Categories
Hotel with Parking


Hotel near Ski Resorts


Hotel for Honeymoon


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Berkshire Cottage in Gorgeous Setting! 4.2 mi from Pittsfield
Vacation Home in Richmond MA
Info Categories
Vacation Home with Parking


Vacation Home with Free Wi-Fi


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Berkshire Cottage 4.2 mi from Pittsfield
Vacation Home in Lanesborough MA
Info Categories
Vacation Home with Parking


Vacation Home near Ski Resorts


Vacation Home with Free Wi-Fi


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Holiday Cottage 4.2 mi from Pittsfield
Vacation Home in Lanesborough MA
Info Categories
Vacation Home with Parking


Vacation Home near Ski Resorts


Vacation Home with Free Wi-Fi


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*Additional taxes or fees may apply. Please check the final price before completing your booking.
Categories:
  •     Parking (294)
  •     Free Wi-Fi (209)
  •     3 Star (112)
  •     Dog Friendly (111)
  •     Ski (88)
  •     Pool (69)
  •     Small (59)
  •     Outdoor Pool (50)
  •     Family (33)
  •     Accessible (27)
  •     4 Star (22)
  •     Luxury (21)
  •     Indoor Pool (16)
  •     Heated Pool (14)
  •     Honeymoon (12)
  •     Business (10)
  •     Gym (9)
  •     EV charging stations (9)
  •     Adult Only (8)
  •     Golf (7)
  •     Sustainability Journey (6)
  •     Rooms with Fireplace (5)
  •     Romantic (4)
  •     Tennis (4)
  •     Boutique-Style (4)
  •     Health & Safety (3)
  •     Historic (2)
  •     5 Star (2)
  •     Private Pool (1)
  •     Yoga (1)
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