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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

Compare 36 Resorts in Old Chatham with updated reviews, rates, and availability.

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 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
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
Lg 1 Bd - Vacation Village in the Berkshires
Lobby

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!"
Lg 1 Bd - Vacation Village in the Berkshires
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
COZY CABIN IN BERKSHIRES RESORT
Outdoor pool, a heated pool

COZY CABIN IN BERKSHIRES RESORT

9.6 out of 10, Exceptional, (16)
"Perfect for a weekend of skiing with the family."
COZY CABIN IN BERKSHIRES RESORT
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

8.6 out of 10, Excellent, (10)
"Great place to stay very clean and comfortable."
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
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
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)
"Easy booking, great ski weekend. Very positive experience!"
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
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!
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
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 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
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
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
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 - 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
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
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
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! 07/13/25 - 07/20/25 REDUCED!
Fridge, microwave, oven, stovetop

5 STAR ESTATE w/ POOL, POND, ARCADE, GYM, TRAILS! 07/13/25 - 07/20/25 REDUCED!

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! 07/13/25 - 07/20/25 REDUCED!
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, (1801)
"Great property"
The price is SAR 443
SAR 527 total
includes taxes & fees
8 May - 9 May
Vacation Village in the Berkshires
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (96)
"Third or fourth time staying. Always a pleasure "
The price is SAR 487
SAR 526 total
includes taxes & fees
13 May - 14 May
Micosta Leisure Inn
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: All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx. - 16.1 mi (25.8 km) from Old Chatham. Has a sauna. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort. 16 mi (25.7 km) from Old Chatham. Enjoy the ski-in/ski-out access, fitness center, and garden. Bentley Brook the perfect home base for exploring nearby Berkshire County - Ski resort. 16.1 mi (25.8 km) from Old Chatham. Amenities include ski-in/ski-out access, a sauna, and a fitness center. Bentley Brook the perfect home base for exploring nearby Berkshire County - Ski resort. 16.1 mi (25.8 km) from Old Chatham. Access to ski-in/ski-out access, a sauna, and a fitness center.
What can I do in Old Chatham?
Shaker Museum and Library, Kinderhook Lake, and The Mac-Haydn Theatre are a few interesting places to visit nearby. Additional attractions in the area include Martin Van Buren National Historic Site and Art Omi International Arts Center - Fields Sculpture Park.
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.