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Compare 26 Resorts in Old Chatham with updated reviews, rates, and availability.

All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
Exterior
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
2.0 star property
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
Exterior
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
10.0 out of 10, Exceptional, (2)
"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
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
8.0 out of 10, Very Good, (6)
"Great time at jiminy! This unit was super clean and super convenient to everything at jiminy including the lodge and lifts! Thank you for the speedy communication! Appreciate it! We’ll be back next year! Thanks!"
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
Exterior
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
Cozy Cabin on resort property in Cultural Berkshires. Labor Day Sale!
Outdoor Pool by our cabin. Open from Memorial Day weekend through end of August.
Cozy Cabin on resort property in Cultural Berkshires. Labor Day Sale!
9.6 out of 10, Exceptional, (14)
"Very nice stay"
Cozy Cabin on resort property in Cultural Berkshires. Labor Day Sale!
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Exterior
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!
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
Exterior
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
10.0 out of 10, Exceptional, (2)
"The property manager was great and very communicative. The hotel is the perfect place to stay if skiing at Jiminy peak. Ski school right outside, pool and arcade room for the children."
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
Exterior
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
Exterior
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
10.0 out of 10, Exceptional, (2)
"Jimney is always a great time"
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
Vacation Village In The Berkshires 5 Star Resort - Suite B
Exterior
Vacation Village In The Berkshires 5 Star Resort - Suite B
Vacation Village In The Berkshires 5 Star Resort - Suite B
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
Exterior
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
10.0 out of 10, Exceptional, (1)
"Great location and overall wonderful stay at Jiminy Peak!"
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
Bentley Brook: Elevate Your Winter Thrills with Premier Ski-In/Ski-Out Luxury
Room
Bentley Brook: Elevate Your Winter Thrills with Premier Ski-In/Ski-Out Luxury
10.0 out of 10, Exceptional, (1)
"Great place to get my 6 year old on the mountain. What a great time !"
Bentley Brook: Elevate Your Winter Thrills with Premier Ski-In/Ski-Out Luxury
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
10.0 out of 10, Exceptional, (1)
"Great spot. We had a ton of fun."
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
Bentley Brook at Jiminy Peak ^ Studio
Exterior
Bentley Brook at Jiminy Peak ^ Studio
Bentley Brook at Jiminy Peak ^ Studio
Slope-Side Ski-in Ski-Out: Bentley Brook Resort
Wyndham Bentley Brook Resort
Slope-Side Ski-in Ski-Out: Bentley Brook Resort
Slope-Side Ski-in Ski-Out: Bentley Brook Resort
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 - Hancock, MA - 2BD, Sleeps 8ppl - A
Exterior
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Pool
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
1 Bedroom - Vacation Village in the Berkshires Resort - Hancock
Property grounds
1 Bedroom - Vacation Village in the Berkshires Resort - Hancock
2.0 star property
1 Bedroom - Vacation Village in the Berkshires Resort - Hancock
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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.
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Other property types in Old Chatham

Beautiful Private Estate! Pool, Pond, Gym, Arcade, Barn, Trails, Library & More!
Beautiful Bellavista Country Estate! Create Timeless Memories w/ Family/ Friends
Beautiful Private Estate! Pool, Pond, Gym, Arcade, Barn, Trails, Library & More!
9.6 out of 10, Exceptional, (84)
"This large home has many comfortable bedrooms, some very large suites. The kitchen is very well stocked. Our family had a wonderful stay. The pool was great, and a center of our enjoyment. Kids also enjoyed the game room."
Beautiful Private Estate! Pool, Pond, Gym, Arcade, Barn, Trails, Library & More!
Vacation Village in the Berkshires
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1714)
"Nice place. Pleasantly surprised how big the suite was. The whole place was very clean from the suite itself, the huge indoor pool and hot tub. The clerk that checked us in was very knowledgeable of the area and just a pleasant person. She is an older lady, I forget her name but she is a definite asset to this property! On the down side the path to the main office was not well lit but we used our flashlights. Also there isn't restaurants on site or groceries available. We had to travel 25...
The price is SAR 633
SAR 732 total
includes taxes & fees
24 Sep - 25 Sep
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (897)
"Was good everything "
The price is SAR 549
SAR 602 total
includes taxes & fees
26 Sep - 27 Sep
Jiminy Peak Mountain Resort
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.

Frequently asked questions

What can I expect from a resort vacation in Old Chatham?
Longing for a relaxing escape? Indulge in the comforts of a resort, where you can find everything you want for your trip from tasty dining options to activities and entertainment. Browse the resorts in the area and discover the right one for you, whether you envision yourself kicking back in a suite with stunning views or checking out the on-site boutiques.
What can I do in Old Chatham?
Shaker Museum and Library, The Mac-Haydn Theatre, and Martin Van Buren National Historic Site are a few interesting places to visit nearby. Additional attractions in the area include Art Omi International Arts Center - Fields Sculpture Park and Hancock Shaker Village.
What's the weather like in Old Chatham?
The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Old Chatham are January, March, December, and April, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around Old Chatham?
Fly into Hudson, NY (HCC-Columbia County), which is located 12.7 mi (20.4 km) from the heart of the city. Otherwise, you can search for flights to Pittsfield, MA (PSF-Pittsfield Municipal), which is 13.9 mi (22.3 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.