Cheshire Resorts
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Resorts in Cheshire
![Ski resort, Wydham Bently Brook in Berkshire mountains, MA](https://images.trvl-media.com/lodging/98000000/97080000/97079800/97079703/80157b1d_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Ski resort, Wydham Bently Brook in Berkshire mountains, MA
With a stay at this resort in Hancock, you'll be a 1-minute drive from Jiminy Peak Mountain Resort and 9 minutes from Mount Greylock State Reservation.
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![Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base](https://images.trvl-media.com/lodging/101000000/100900000/100899400/100899305/fe474181_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
With a stay at this resort in Hancock, you'll be a 1-minute drive from Jiminy Peak Mountain Resort and 9 minutes from Mount Greylock State Reservation.
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![Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out](https://images.trvl-media.com/lodging/97000000/96990000/96987700/96987624/w1024h614x0y34-f95f15b1_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
With a stay at this resort in Hancock, you'll be in the mountains, within a 10-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State Reservation.
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![In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants](https://images.trvl-media.com/lodging/96000000/95770000/95763800/95763744/f5813f2b_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
With a stay at this resort in Hancock, you'll be in the mountains, within a 10-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State Reservation.
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Hot Tub
![Cozy Cabin on resort property in Cultural Berkshires. Pets are welcome!](https://images.trvl-media.com/lodging/79000000/78440000/78431000/78430936/1a1aaa8a_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Cozy Cabin on resort property in Cultural Berkshires. Pets are welcome!
With a stay at this resort in Hancock, you'll be in the mountains, within a 10-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State Reservation.
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![Hot SKI-in SKI-out Rentals Bentley Brook Resort!](https://images.trvl-media.com/lodging/71000000/70600000/70595300/70595216/4db4d626_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
With a stay at this resort in Hancock, you'll be a 1-minute drive from Jiminy Peak Mountain Resort and 8 minutes from Mount Greylock State Reservation.
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![Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury](https://images.trvl-media.com/lodging/102000000/101270000/101263700/101263676/5a54e43d_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
With a stay at this resort in Hancock, you'll be a 1-minute drive from Jiminy Peak Mountain Resort and 9 minutes from Mount Greylock State Reservation.
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Hot Tub
![Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort](https://images.trvl-media.com/lodging/102000000/101090000/101081700/101081653/00e7014d_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
With a stay at this resort in Hancock, you'll be a 1-minute drive from Jiminy Peak Mountain Resort and 9 minutes from Mount Greylock State Reservation.
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![Vacation Village In The Berkshires 5 Star Resort - Suite B](https://images.trvl-media.com/lodging/37000000/36830000/36822800/36822714/309fdcd3_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Vacation Village In The Berkshires 5 Star Resort - Suite B
With a stay at this resort in Hancock, you'll be in the mountains, within a 10-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State Reservation.
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![Bentley Brook: Ultimate Ski-In Ski-Out -Crazy](https://images.trvl-media.com/lodging/102000000/101360000/101352000/101351994/4618129f_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
With a stay at this resort in Hancock, you'll be a 1-minute drive from Jiminy Peak Mountain Resort and 9 minutes from Mount Greylock State Reservation.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Cheshire Resorts essential information
Accommodation | 21 Resorts |
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Lowest Price | |
Highest Price | |
Popular accommodation | Ski resort, Wydham Bently Brook in Berkshire mountains, MA, Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base, Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out, In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants, Cozy Cabin on resort property in Cultural Berkshires. Pets are welcome!, Hot SKI-in SKI-out Rentals Bentley Brook Resort!, Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury , Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort , Vacation Village In The Berkshires 5 Star Resort - Suite B, Bentley Brook: Ultimate Ski-In Ski-Out -Crazy, Pres Week- Bentley Brook Resort - Your Peak Winter Escape, Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out |