Harbour House Inn
Bed & Breakfast in Cheshire MA
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Bed & Breakfast with Parking


Bed & Breakfast near Ski Resorts


Bed & Breakfast with Free Wi-Fi


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Massachusetts Vacation Rental with Deck and Grill
Vacation Home in Cheshire MA
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Vacation Home with Parking


Dog Friendly Vacation Home


Vacation Home with Free Wi-Fi


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234 more hotels nearby!
Charming Adams Home Near Dtwn, Trails and More! 3.1 km from Cheshire
Vacation Home in Adams MA
10
Excellent
Info Categories
Vacation Home with Parking


Vacation Home with Free Wi-Fi


Accessible Vacation Home


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Mountain getaway in the Berkshires - walk to trails & town! 3.5 km from Cheshire
Vacation Home in Adams MA
10
Excellent
Info Categories
Vacation Home with Parking


Vacation Home near Golf Courses


Family Friendly Vacation Home


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Cozy Rustic Apt in 18th c Berkshire Farmhouse 4.9 km from Cheshire
Apartment in Lanesborough MA
9.5
Excellent
Info Categories
Apartment with Parking


Apartment with Free Wi-Fi


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Bright Boho Apt in 18th c Berkshire Farmhouse 4.9 km from Cheshire
Apartment in Lanesborough MA
9.0
Excellent
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Apartment with Parking


Family Friendly Apartment


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The Springs Motel 4.9 km from Cheshire
Hotel in New Ashford MA
8.2
Very Good
Info Categories
Hotel with Parking


Hotel near Ski Resorts


Hotel for Honeymoon


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Mount Royal Inn 5.4 km from Cheshire
Hotel in Adams MA
8.0
Very Good
From $99
From $99
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Hotel with Parking


Luxury Hotel


Dog Friendly Hotel


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lanesborough Country inn 6.8 km from Cheshire
Hotel in Lanesborough MA
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Hotel with Parking


Small Hotel


5-Star Hotel


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Mountainside Condo @ Jiminy Peak in the Berkshires 7.0 km from Cheshire
Vacation Home in Hancock MA
8.0
Very Good
Info Categories
Vacation Home with Parking


Vacation Home near Golf Courses


Family Friendly Vacation Home


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Scenic Hancock Retreat 4 Mi to Jiminy Peak! 7.0 km from Cheshire
Vacation Home in Hancock MA
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Vacation Home with Parking


Vacation Home with Free Wi-Fi


3-Star Vacation Home


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Jiminy Peak Vacation Home 7.0 km from Cheshire
Vacation Home in Hancock MA
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Vacation Home with Parking


Vacation Home near Ski Resorts


Vacation Home with Swimming Pool

Heated Pool    Indoor Pool    Outdoor Pool  


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Jiminy Peak Mountainside Getaway in the Berkshires 7.0 km from Cheshire
Vacation Home in Hancock MA
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Vacation Home with Parking


Vacation Home near Golf Courses


Family Friendly Vacation Home


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Spacious 3BR 3BA Sleeps 8 Ski On Off Jiminy Mountain Resort 7.0 km from Cheshire
Vacation Home in Hancock MA
9.0
Excellent
Info Categories
Vacation Home with Parking


Dog Friendly Vacation Home


Vacation Home with Swimming Pool

Outdoor Pool  


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Berkshire Cottage 7.1 km from Cheshire
Vacation Home in Lanesborough MA
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Vacation Home with Parking


Vacation Home near Ski Resorts


Vacation Home with Free Wi-Fi


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Holiday Cottage 7.1 km from Cheshire
Vacation Home in Lanesborough MA
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Vacation Home with Parking


Vacation Home near Ski Resorts


Vacation Home with Free Wi-Fi


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Writers Cottage 7.1 km from Cheshire
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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Greylock Cottage 7.1 km from Cheshire
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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Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak 7.2 km from Cheshire
Vacation Home in Hancock MA
10
Excellent
Info Categories
Vacation Home with Parking


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 7.2 km from Cheshire
Vacation Home in Hancock MA
9.5
Excellent
Info Categories
Vacation Home with Parking


Vacation Home with Swimming Pool

Indoor Pool    Outdoor Pool  


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 (236)
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  •     3 Star (98)
  •     Ski (87)
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