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Browse Select Hancock B&B

Club Wyndham Bentley Brook
Exterior

Club Wyndham Bentley Brook

3.0 star property
9.2 out of 10, Wonderful, (495)
"Better than expected! No complaints! Very impressed with the staff! Every staff member we encountered was kind, professional, helpful and pleasant! From the front desk employees, to the men who were taking care of the pool, to the staff shoveling snow and salting, to the women we observed pushing these heavy wagons to the gentleman responding to a service call who helped us find our way around….very impressive! It was our first time here and we’re discussing our next trip back with friends!...
Club Wyndham Bentley Brook
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

8.4 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
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, (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...
SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!
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-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
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, (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
Lobby

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

Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
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: Ultimate Ski-In Ski-Out -Crazy
Dining

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
Xmas in Hancock @ Jiminy Premier Ski-In/Ski-Out Resort
Dining

Xmas in Hancock @ Jiminy Premier Ski-In/Ski-Out Resort

10.0 out of 10, Exceptional, (2)
"Great place to get my 6 year old on the mountain. What a great time !"
Xmas in Hancock @ Jiminy Premier Ski-In/Ski-Out Resort
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, (1)
"Great spot. We had a ton of fun."
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
Dining

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
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.
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
Dining

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
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 Hancock

Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (922)
"It’s challenging to read the reviews and know what to expect for this hotel. One main reason for that is because each unit is owned by different owners. Some units may have been renovated more recently than other units. I booked 3 rooms. One unit had an old electric stove with coils while the other had a newer electric stove. 1 had a toaster oven while the others did not. We brought food to cook, but kept it simple because we didn’t know what cooking pots and utensils would be available. One...
The price is CA $271
CA $297 total
includes taxes & fees
Jan 20 - Jan 21
Jiminy Peak Mountain Resort
Mountainside Condo Ski In Ski Out
Pool

Mountainside Condo Ski In Ski Out

9.0 out of 10, Wonderful, (21)
"Stay at Jiminey for the 13 nights. Condo was clean and had anything you could ever need! "
The price is CA $214
CA $269 total
includes taxes & fees
Jan 20 - Jan 21
Mountainside Condo Ski In Ski Out
Family-Friendly Hancock Home: Walk to Slopes!
Interior

Family-Friendly Hancock Home: Walk to Slopes!

9.8 out of 10, Exceptional, (16)
"The instructions were clear. Mike was easy to talk to and very polite. He answered all questions asked. The place was clean and there were plenty of plates, pots, utensils, and cleaning agents. We enjoyed our stay and are willing to come back."
Family-Friendly Hancock Home: Walk to Slopes!
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

Searching for B&Bs in Hancock?
If you’re looking for something a little quirkier than the traditional hotel experience, a bed and breakfast could be the perfect alternative for your vacation. If you’re looking to hit the slopes on your trip to Hancock, Jiminy Peak Mountain Resort is worth a visit.
Why would you choose a B&B over a traditional hotel room?
With attentive service, opportunities to meet guests from other places, and of course a full breakfast, B&Bs provide a truly one-of-a-kind setting.
What are the top B&Bs in Hancock?
Below are some B&Bs in the surrounding area: The Cornell Inn, Lenox: 12.5 mi (20.2 km) from the heart of Hancock. Enjoy the free full breakfast and unique décor. Lakehouse Inn: 14 rooms. 15.4 mi (24.7 km) from the downtown core. Enjoy the free full breakfast and deli. Chambery Inn: 9 rooms. Situated 16.6 mi (26.7 km) from the heart of Hancock. Enjoy the private yard and deli. Shaker Mill Inn: 9 rooms. 15.3 mi (24.7 km) from the heart of downtown.Brook Farm Inn: 15 rooms. Located 13.5 mi (21.7 km) from the core of Hancock. Enjoy the free cooked breakfast and outdoor pool.
What's the best time of year to stay at a B&B in Hancock?
When you’re dreaming of a getaway to Hancock, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Hancock are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Hancock?
If you’re looking for some things to do on your trip, travelers enjoy Hancock for its skiing and hiking. If you’re looking to find something to do during your travels, you might consider checking out Alpine Super Slide and Mountain Coaster. You might check out Jiminy Peak Mountain Resort if you have time to see more of the area.
How can I get to and around Hancock?
Mapping out your trip in and around Hancock is easy with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 8.5 mi (13.6 km) from the heart of the city. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 28.1 mi (45.2 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.