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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

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

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

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

9.6 out of 10, Exceptional, (4)
"Na"
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
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)
"Fun time. Conditions were good. We love this family Mountain "
Jiminy Premier Ski-In/Ski-Out Resort Bentley B
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)
"My family had a blast here and appreciate the availability. The property is situated perfectly for skiing on/off of Jiminy Cricket. Ski lockers made it even easier. We loved the spacious rooms, whirlpool bath, laundry and kitchen. My son said he wanted to move in :) Towels for bath and pool, coffee & filters, and laundry detergent provided. Free wifi and plenty of activities if you aren't skiing or apres-ski. There are 2 EV charging stations at one of the buildings and front desk avail 24/7. "
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
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 at Jiminy Peak - 2 Bedroom - ski in/out
Lobby

Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out

Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!
Outdoor pool, a heated pool

SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!

9.6 out of 10, Exceptional, (16)
"The cabin is exactly as pictured. Kim was nice enough to let us check in early and check out late and left some bottles of water for us. It's a 5-10 minute walk to the slopes with kids and gear on, but close to the hotel and the convenience store. Note that the outdoor pool nearby is closed when it's under 25 degrees. Also note that the beds are soft, but other than that we had a wonderful stay and would recommend! "
SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!
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, (9)
"Great place to stay. Easy access to the mountain and great layout for our family."
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
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
9.8 out of 10, Exceptional, (38)
"Stay was perfect all you need "
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
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 resort is ski in ski out . You can’t beat that . The rooms are specious and kitchen and living room are add space. Everything is right there . Pool and hot tubs are great after skiing. We love Bentley Brook has been coming here for 8 years "
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!
Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires
Lobby

Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires

2.0 star property
10.0 out of 10, Exceptional, (2)
"We enjoyed staying at this clean, quiet, and comfy property. Close to so many beautiful spots! Only minutes to both New York and Vermont!"
Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires
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
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
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, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort
Lobby

Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort

10.0 out of 10, Exceptional, (1)
"We spent a lovely weekend at the Bentley Brook with our kids. The condo is about 200 feet from the nearest lift. The condo is comfortable and spacious. Don't hesitate.."
Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort
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
Vacation Village in the Berkshires 5 Star Resort - Suite A
Indoor pool, outdoor pool

Vacation Village in the Berkshires 5 Star Resort - Suite A

Vacation Village in the Berkshires 5 Star Resort - Suite A
Bentley Brook at Jiminy Peak ^ Studio
Exterior

Bentley Brook at Jiminy Peak ^ Studio

Bentley Brook at Jiminy Peak ^ Studio
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)
"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
Dining

Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort

Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out 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.
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Other property types in Old Chatham

5 STAR ESTATE w/ POOL, POND, ARCADE, GYM, TRAILS! ASK ABOUT FANTASTIC DISCOUNT!
Fridge, microwave, oven, stovetop

5 STAR ESTATE w/ POOL, POND, ARCADE, GYM, TRAILS! ASK ABOUT FANTASTIC DISCOUNT!

9.6 out of 10, Exceptional, (85)
"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"
5 STAR ESTATE w/ POOL, POND, ARCADE, GYM, TRAILS! ASK ABOUT FANTASTIC DISCOUNT!
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"Very nice accomodations, more like a mini apartment than a motel room. "
The price is SAR 484
SAR 572 total
includes taxes & fees
25 Mar - 26 Mar
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is SAR 503
SAR 552 total
includes taxes & fees
6 Apr - 7 Apr
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's the best resort in Old Chatham?
Our top-rated resorts around Old Chatham: In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 16 mi (25.7 km) from Old Chatham. Has ski-in/ski-out access, a fitness center, and a garden. SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires! - Ski resort right by Jiminy Peak Mountain Resort. 15.9 mi (25.6 km) from Old Chatham. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers. All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx. - Only a 5-minute walk from Jiminy Peak Mountain Resort. 16.1 mi (25.8 km) from Old Chatham. Amenities include a sauna.
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 November, 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.