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Resorts in Cheshire

All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
Lobby

All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.

2.0 star property
10.0 out of 10, Exceptional, (44)
"Great place and location!"
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
Bentley Brook the perfect home base for exploring nearby Berkshire County
Exterior

Bentley Brook the perfect home base for exploring nearby Berkshire County

10.0 out of 10, Exceptional, (3)
"We just spent a couple nights here but enjoyed our time here. There was plenty of room for 4 people and it was a close walk to the base of Jiminy Peak for the adventure park. Staff was helpful and friendly as well. "
Bentley Brook the perfect home base for exploring nearby Berkshire County
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Interior

In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

8.8 out of 10, Excellent, (11)
"Great place to stay very clean and comfortable."
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Bentley Brook the perfect home base for exploring nearby Berkshire County
Exterior

Bentley Brook the perfect home base for exploring nearby Berkshire County

Bentley Brook the perfect home base for exploring nearby Berkshire County
COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY.
Outdoor pool, a heated pool

COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY.

9.6 out of 10, Exceptional, (17)
"Perfect for a weekend of skiing with the family."
COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY.
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Property grounds

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!

10.0 out of 10, Exceptional, (1)
"We loved everything about this place! It was quiet, centrally located, and everyone was friendly and helpful. We will stay here again for sure!"
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Bentley Brook the perfect home base for exploring nearby Berkshire County
Exterior

Bentley Brook the perfect home base for exploring nearby Berkshire County

10.0 out of 10, Exceptional, (1)
Bentley Brook the perfect home base for exploring nearby Berkshire County
1 Bd - Vacation Village in the Berkshires
Lobby

1 Bd - Vacation Village in the Berkshires

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great spot"
1 Bd - Vacation Village in the Berkshires
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Property grounds

Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A

10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay and it was nice to be so close to the slopes."
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B
Property grounds

Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B

Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B
Vacation Village In The Berkshires 5 Star Resort - Suite B
Indoor pool, outdoor pool

Vacation Village In The Berkshires 5 Star Resort - Suite B

Vacation Village In The Berkshires 5 Star Resort - Suite B
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
Dining

Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

10.0 out of 10, Exceptional, (6)
"Great location, clean and perfect for a family! "
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
Dining

Pres Week- Bentley Brook Resort - Your Peak Winter Escape

9.6 out of 10, Exceptional, (4)
"Bentley Brook is the ideal location for a young family on a ski trip!"
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
Dining

Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base

10.0 out of 10, Exceptional, (3)
"This property is great for skiing, especially with kids. There is a nice pool and little movie theater thats prefect for after a day on the slopes."
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Dining

Hot SKI-in SKI-out Rentals Bentley Brook Resort!

10.0 out of 10, Exceptional, (1)
"Great property! Great location. Smooth check-in."
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Jiminy Premier Ski-In/Ski-Out Resort Bentley B
Dining

Jiminy Premier Ski-In/Ski-Out Resort Bentley B

10.0 out of 10, Exceptional, (2)
"Great place to get my 6 year old on the mountain. What a great time !"
Jiminy Premier Ski-In/Ski-Out Resort Bentley B
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
Exterior

Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl

10.0 out of 10, Exceptional, (1)
"Large property with ski-in/ski-out proximity to Jiminy Peak. Units are standard but large, clean, and with helpful amenities for a family vacation (kitchenette in unit, plus nice pool for kids' apres-ski, kids' movies, etc.) We'll be back."
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
Dining

Bentley Brook: Ultimate Ski-In Ski-Out -Crazy

9.6 out of 10, Exceptional, (4)
"Very easy access to the slope and perfect for family with kids"
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
Dining

Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury

10.0 out of 10, Exceptional, (2)
"This condo was perfect for our family. We had lots of space and we were right on the base of Jiminy peak. I would definitely stay again."
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
Dining

Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss

10.0 out of 10, Exceptional, (1)
"Walked out of the building, straight into my kids skiing lessons, very convenient."
Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
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.
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Top Cheshire Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"I honestly just spent the night as part of a longer road-trip, but I found it quiet and comfortable, and the room was very clean when I arrived. Slept well, but unfortunately had to leave before breakfast."
Eric 1-night trip
Posted 6 hours ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

What is Cheshire like for a resort vacation?
You deserve a vacation, and a resort is just the place to find all the amenities and services you need for a relaxing trip to Cheshire. One of the comfortable resorts in the area might be just what you're looking for, whether you're hoping for a luxurious suite, shopping possibilities, or fun activities to try.
What's the best resort for my stay in Cheshire?
Here's our top-rated resort near Cheshire: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 20.6 mi (33.2 km) from Cheshire. Access to a sauna, a fitness center, and a terrace.
What can I do in Cheshire?
Mount Greylock State Reservation, St Mary's of the Assumption Church, and Mount Greylock State Reservation Visitor Center are a few interesting places to visit nearby. In the area, other attractions include Mount Greylock and Brodie Mountain.
What's the weather like in Cheshire?
The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around Cheshire?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 11.5 mi (18.5 km) from the city center. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.