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Compare 25 Resorts in Housatonic 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
Snow and ski sports

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
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
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Room

In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

8.4 out of 10, Very Good, (7)
"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
Cozy Cabin on resort property in Cultural Berkshires.
Outdoor Pool by our cabin. Open from Memorial Day weekend through end of August.

Cozy Cabin on resort property in Cultural Berkshires.

9.6 out of 10, Exceptional, (15)
"Kim is a wonderful host, and her cabin is just perfect. This is my second time staying at her place, since I like to travel with my dog whenever possible. Very roomy with a high ceiling, but still nice and toasty. It has everything you could want in a full kitchen, and there’s also a great restaurant and country store/deli just a few steps away. We had a great time at the haunt this Halloween season, which I had never done before. Lots of fun things to do, and gorgeous hikes in the area. I have...
Cozy Cabin on resort property in Cultural Berkshires.
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Snow and ski sports

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
Snow and ski sports

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
Snow and ski sports

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
Snow and ski sports

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
Snow and ski sports

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
Snow and ski sports

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
Snow and ski sports

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
Snow and ski sports

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!

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!
Cozy and large 2 Bedroom 2 Full Bath ski in, ski out condo Unit with balcony.
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.
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 Housatonic

Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AED 547
AED 600 total
includes taxes & fees
27 Nov - 28 Nov
Jiminy Peak Mountain Resort
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.8 out of 10, Exceptional, (37)
"Beautiful property located in the woods with plenty of privacy. 3 floors with a lot of elbow room and a tennis court also! Very good communication with the owners with easy check in/check out instructions. "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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 Housatonic?
You deserve a getaway, and a resort is the perfect place to pamper yourself with the services and amenities you need for a relaxing stay in Housatonic. One of the comfortable resorts in the surrounding area could be just what you’re searching for, whether you’re hoping for great restaurants on site, a state-of-the-art fitness center, or nightly entertainment options.
What's a favorite resort in Housatonic?
Here are our top-rated resorts near Housatonic: In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 20.6 mi (33.2 km) from Housatonic. Has ski-in/ski-out access, a fitness center, and a garden. Cozy Cabin on resort property in Cultural Berkshires. - Ski resort right by Jiminy Peak Mountain Resort. 20.6 mi (33.2 km) from Housatonic. 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. 20.7 mi (33.3 km) from Housatonic. Amenities include a sauna.
What can I do in Housatonic?
Housatonic River, Norman Rockwell Museum, and Berkshire Botanical Garden are a few interesting places to visit nearby. Other attractions in the area include Naumkeag Museum and National Shrine of the Divine Mercy.
What's the weather like in Housatonic?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Housatonic 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 Housatonic?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 11.9 mi (19.1 km) away from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 17.5 mi (28.1 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.