Hancock Village Inn at Jiminy Peak 7.7 mi from Pittsfield
Vacation Home in Hancock MA
10
Excellent
Info Categories
3-Star Vacation Home


Family Friendly Vacation Home


Vacation Home with Free Wi-Fi


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Berkshire Retreat- A stone's throw to downtown Lenox 7.7 mi from Pittsfield
Vacation Home in Stockbridge MA
Info Categories
3-Star Vacation Home


Dog Friendly Vacation Home


Vacation Home with Free Wi-Fi


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Stockbridge Home Walk to Town Beach! 7.9 mi from Pittsfield
Vacation Home in Stockbridge MA
8.0
Very Good
Info Categories
3-Star Vacation Home


Vacation Home with Free Wi-Fi


Vacation Home with Parking


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Spacious 3BR 3BA Sleeps 8 Ski On Off Jiminy Mountain Resort 8.1 mi from Pittsfield
Vacation Home in Hancock MA
9.0
Excellent
Info Categories
3-Star Vacation Home


Dog Friendly Vacation Home


Vacation Home with Swimming Pool

Outdoor Pool  


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Berkshire Vacation Rentals: Private Cottage Come Enjoy Nature 8.1 mi from Pittsfield
Vacation Home in Canaan NY
Info Categories
3-Star Vacation Home


Vacation Home with Free Wi-Fi


Vacation Home with Parking


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Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 8.1 mi from Pittsfield
Vacation Home in Hancock MA
9.1
Excellent
Info Categories
3-Star Vacation Home


Vacation Home with Swimming Pool

Indoor Pool    Outdoor Pool  


Vacation Home with Free Wi-Fi


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Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak 8.1 mi from Pittsfield
Vacation Home in Hancock MA
8.8
Excellent
Info Categories
3-Star Vacation Home


Vacation Home with Swimming Pool

Outdoor Pool  


Vacation Home with Free Wi-Fi


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Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn 8.1 mi from Pittsfield
Vacation Home in Hancock MA
9.0
Excellent
Info Categories
3-Star Vacation Home


Vacation Home with Free Wi-Fi


Vacation Home with Parking


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Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor 8.1 mi from Pittsfield
Apartment in Hancock MA
Info Categories
3-Star Apartment


Apartment with Swimming Pool

Indoor Pool    Outdoor Pool  


Apartment with Free Wi-Fi


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Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak 8.1 mi from Pittsfield
Vacation Home in Hancock MA
10
Excellent
Info Categories
3-Star Vacation Home


Vacation Home with Swimming Pool

Indoor Pool    Outdoor Pool  


Vacation Home with Free Wi-Fi


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Gorgeous 1st FL Mtn View Jiminy Suite Sleeps 4 Ski On Off 8.1 mi from Pittsfield
Vacation Home in Hancock MA
9.5
Excellent
Info Categories
3-Star Vacation Home


Vacation Home with Swimming Pool

Indoor Pool    Outdoor Pool  


Vacation Home with Free Wi-Fi


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The Black Swan Lee - Lenox, Ascend Hotel Collection 8.1 mi from Pittsfield
Hotel in Lee MA
8.3
Very Good
From $103
From $103
Info Categories
3-Star Hotel


Hotel near Ski Resorts


Hotel Taking Steps Towards Sustainability


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Club Wyndham Bentley Brook 8.2 mi from Pittsfield
Hotel in Hancock MA
8.6
Very Good
From $113
From $113
Info Categories
3-Star Hotel


Hotel near Ski Resorts


Hotel for Honeymoon


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WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk 8.2 mi from Pittsfield
Vacation Home in Hancock MA
9.7
Excellent
Info Categories
3-Star Vacation Home


Vacation Home with Swimming Pool

Outdoor Pool  


Vacation Home with Free Wi-Fi


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Jurassic Dino Suite Jiminy-Must See Sleeps 4 8.2 mi from Pittsfield
Vacation Home in Hancock MA
9.0
Excellent
Info Categories
3-Star Vacation Home


Vacation Home with Swimming Pool

Indoor Pool  


Vacation Home with Free Wi-Fi


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Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy 8.2 mi from Pittsfield
Vacation Home in Hancock MA
9.0
Excellent
Info Categories
3-Star Vacation Home


Vacation Home with Swimming Pool

Outdoor Pool  


Vacation Home with Free Wi-Fi


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Jiminy Peak Mountain Resort 8.2 mi from Pittsfield
Resort in Hancock MA
7.6
Good
From $163
From $163
Info Categories
3-Star Resort


Resort near Golf Courses


Resort with Ski To Door Access


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Updated Canaan Farmhouse Pond and Sunset Views! 8.4 mi from Pittsfield
Vacation Home in Canaan NY
10
Excellent
Info Categories
3-Star Vacation Home


Vacation Home with Swimming Pool


Vacation Home with Free Wi-Fi


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Berkshire Vacation Rentals: Centrally Located Historical Home 8.6 mi from Pittsfield
Vacation Home in Lee MA
Info Categories
3-Star Vacation Home


Vacation Home with Free Wi-Fi


Vacation Home with Parking


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Pet-Friendly Canaan Home Near Queechy Lake! 8.7 mi from Pittsfield
Vacation Home in Canaan NY
Info Categories
3-Star Vacation Home


Dog Friendly Vacation Home


Vacation Home with Swimming Pool


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*Additional taxes or fees may apply. Please check the final price before completing your booking.
Categories:
  •     3 Star (132)
  •     Parking (112)
  •     Free Wi-Fi (105)
  •     Dog Friendly (48)
  •     Pool (38)
  •     Ski (32)
  •     Outdoor Pool (24)
  •     Accessible (19)
  •     Small (17)
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  •     Tennis (4)
  •     Rooms with Fireplace (3)
  •     Historic (2)
  •     EV charging stations (1)
  •     Golf (1)
  •     Ski In Ski Out (1)
  •     Adult Only (1)
  •     Health & Safety (1)
  •     Rooms with Jacuzzi / Hot-Tub (1)
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