Search Resorts in Chatham

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Find properties with these dates

Tonight
May 3 - May 4
Tomorrow
May 4 - May 5
This weekend
May 3 - May 5
Interior
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
Interior
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!
Interior
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
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Interior
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
Pool
Cozy Cabin on resort property in Cultural Berkshire. Pets are welcome!
9.8 out of 10, Exceptional, (13)
"Very nice stay"
Cozy Cabin on resort property in Cultural Berkshire. Pets are welcome!
Exterior
Ski resort, Wydham Bently Brook in Berkshire mountains, MA
Ski resort, Wydham Bently Brook in Berkshire mountains, MA
Interior
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
Property grounds
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Interior
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
Exterior
Cozy and large 2 Bedroom 2 Full Bath ski in, ski out condo Unit with balcony.
Cozy and large 2 Bedroom 2 Full Bath ski in, ski out condo Unit with balcony.
Private kitchen
Mountain Lodge Apt!
Mountain Lodge Apt!
Property grounds
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B
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See all available properties in Chatham
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.

Other property types in Chatham

7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (28)
"We've stayed in a lot of home rentals - and across the board - this was the best place ever. The home was clean, nicely decorated and super comfortable. The hosts were easy to get a hold of and incredibly welcoming, leaving us with a generous basket of local treats. We loved the peaceful outdoor space and roamed all 40 acres. The pond was beautiful and if it had only been warmer we'd have jumped in the rowboat. We will be back for sure. A++ Thank you, Anna!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1672)
"Very nice spot quiet "
The price is HK$1,319
HK$1,525 total
includes taxes & fees
4 May - 5 May
Vacation Village in the Berkshires
Private kitchen
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (856)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is HK$1,164
HK$1,277 total
includes taxes & fees
8 May - 9 May
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.

Chatham Resorts information

Number of reviews
19
Accommodation
12 Resorts
Lowest Price
Highest Price

Frequently asked questions

What can I expect from a resort holiday in Chatham?
You deserve a break, and a resort is just the place to find all the amenities and services you need for a relaxing trip to Chatham. One of the comfortable resort hotels in the surrounding 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 a favourite resort for my stay in Chatham?
Here’s our top-rated resort near Chatham: Cozy Cabin on resort property in Cultural Berkshire. Pets are welcome! - Ski resort. 20.4 mi (32.8 km) from Chatham. Enjoy the ski-in/ski-out access, fitness centre and beach sunloungers.
What can I do in Chatham?
Experience the local theatre scene at The Mac-Haydn Theatre, or take the kids to Berkshire Botanical Garden for some family fun. In the area, other attractions include Martin Van Buren National Historic Site and Kinderhook Lake.
What's the weather like in Chatham?
The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chatham are January, March, February and November, with each month seeing an average of 18 cm 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. You can also search 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, consider renting a car to explore more sights.

Recent Hotel Reviews in Chatham
Expedia verified reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent
"Our room was on the lake and had a nice deck where we could relax with a beer purchased (very cheap!) from the front reception area. Also the Indian restaurant was excellent with ample portions. And because it's in MA, everything was ADA accessible which made it feel inclusive to all. Some guest had their dogs with them but the place was very clean even with pets. "
A verified traveller stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 15 hours ago
The Black Swan Lee - Lenox, Ascend Hotel Collection