Search Resorts in Chatham

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 42 Resorts in 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 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 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
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
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
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
COZY CABIN IN BERKSHIRES RESORT - LABOR DAY SALE
Outdoor pool, a heated pool

COZY CABIN IN BERKSHIRES RESORT - LABOR DAY SALE

9.6 out of 10, Exceptional, (16)
"Perfect for a weekend of skiing with the family."
COZY CABIN IN BERKSHIRES RESORT - LABOR DAY SALE
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
Bentley Brook 1-bedroom Mountainside ski resort in charming Hancock sleeps 8
Pool

Bentley Brook 1-bedroom Mountainside ski resort in charming Hancock sleeps 8

10.0 out of 10, Exceptional, (1)
"the property was great we had a good time Liana was great answered all of my questions got back to me within a few min and also foud a place for a friend when they couldnt also gaveus a free up grade"
Bentley Brook 1-bedroom Mountainside ski resort in charming Hancock sleeps 8
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
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
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
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 at Jiminy Peak ^ Studio
Exterior

Bentley Brook at Jiminy Peak ^ Studio

Bentley Brook at Jiminy Peak ^ Studio
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!
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
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

What can I expect from a resort vacation in Chatham?
You deserve a break, and a resort is the ideal place to treat yourself to the amenities and services you need for a relaxing stay in Chatham. One of the comfortable resort hotels in the surrounding area might be just what you’re looking for, whether you’re hoping for great restaurants on site, a state-of-the-art fitness center, or activities for the kids.
What's the best resort for my stay in Chatham?
Here are our top-rated resorts around Chatham: All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx. - 20.5 mi (33 km) from Chatham. Has a sauna. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort. 20.4 mi (32.8 km) from 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. 20.5 mi (33 km) from 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. 20.5 mi (33 km) from Chatham. Access to ski-in/ski-out access, a sauna, and a fitness center.
What can I do in Chatham?
Experience the local theater scene at The Mac-Haydn Theatre, or bring the kids to Berkshire Botanical Garden for some family fun. In the area, other attractions include Art Omi International Arts Center - Fields Sculpture Park and Martin Van Buren National Historic Site.
What's the seasonal weather like in 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 Chatham 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 Chatham?
Fly into Hudson, NY (HCC-Columbia County), which is located 7.7 mi (12.4 km) away from the city center. Otherwise, look for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 16 mi (25.8 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.