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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare 25 Resorts in Drury with updated reviews, rates, and availability.

Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
Dining

Bentley Brook: Ultimate Ski-In Ski-Out -Crazy

9.6 out of 10, Exceptional, (4)
"Na"
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
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)
"Fun time. Conditions were good. We love this family Mountain "
Jiminy Premier Ski-In/Ski-Out Resort Bentley B
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 resort is ski in ski out . You can’t beat that . The rooms are specious and kitchen and living room are add space. Everything is right there . Pool and hot tubs are great after skiing. We love Bentley Brook has been coming here for 8 years "
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
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)
"Responsive and informative host. Great location ski out. "
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

9.6 out of 10, Exceptional, (4)
"My family had a blast here and appreciate the availability. The property is situated perfectly for skiing on/off of Jiminy Cricket. Ski lockers made it even easier. We loved the spacious rooms, whirlpool bath, laundry and kitchen. My son said he wanted to move in :) Towels for bath and pool, coffee & filters, and laundry detergent provided. Free wifi and plenty of activities if you aren't skiing or apres-ski. There are 2 EV charging stations at one of the buildings and front desk avail 24/7. "
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
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 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
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!
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

8.8 out of 10, Excellent, (9)
"Great place to stay. Easy access to the mountain and great layout for our family."
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
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!
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
Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires
Lobby

Ski Jiminy Peak - 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!"
Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires
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

Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski 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
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
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
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
Bentley Brook at Jiminy Peak ^ Studio
Exterior

Bentley Brook at Jiminy Peak ^ Studio

Bentley Brook at Jiminy Peak ^ Studio
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
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 Drury

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, (1786)
"It was very nice. Had a kitchen and 2 tvs!"
The price is AED 437
AED 520 total
includes taxes & fees
16 Mar - 17 Mar
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 547
AED 600 total
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is AED 551
AED 841 total
includes taxes & fees
16 Mar - 17 Mar
Berkshire Village Carriage House - Super Private!!
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 Drury?
Longing for a relaxing escape? You deserve the luxuries and comforts of a resort, where you can find everything you want for your vacation from convenient food and drink options to entertainment and shopping. Browse the resorts in the area and discover the right one for you, whether you see yourself kicking back in a luxury suite or heading to the spa for a deep-tissue massage.
What's a favorite resort for my stay in Drury?
Our highest-rated resorts near Drury: Bentley Brook: Ultimate Ski-In Ski-Out -Crazy - Family-friendly resort, 5-minute walk from Jiminy Peak Mountain Resort. 16.5 mi (26.6 km) from Drury. Features a fitness center, an indoor pool, and an outdoor pool. Jiminy Premier Ski-In/Ski-Out Resort Bentley B - Only a 5-minute walk from Jiminy Peak Mountain Resort. 16.5 mi (26.6 km) from Drury. Has a fitness center, an indoor pool, and an outdoor pool. All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx. - Only a 5-minute walk from Jiminy Peak Mountain Resort. 16.5 mi (26.6 km) from Drury. Amenities include a sauna. Bentley Brook Resort: Premier Retreat at Jiminy Peak’s Base - Situated just a 5-minute walk from Jiminy Peak Mountain Resort. 16.5 mi (26.6 km) from Drury. Access to a fitness center and a hot tub.
What can I do in Drury?
If you’re interested in local sights, Tannery Falls, Hoosac Range, and Zoar Outdoor/Deerfield Valley Canopy Tours are some places to visit nearby. Other attractions in the area include Berkshire East Ski Resort and Bissell Covered Bridge.
What's the seasonal weather like in Drury?
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 Drury 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 Drury?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 21.6 mi (34.8 km) away from the heart of the city. If you’d like to venture out around the area, you may want a rental car for your journey.