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Compare 31 Resorts in Lenox with updated reviews, rates, and availability.

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

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.

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

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

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

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

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!

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

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

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

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!

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

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

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

Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort

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

Vacation Village in the Berkshires 5 Star Resort - Suite A

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

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

Bentley Brook at Jiminy Peak ^ Studio
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 Lenox

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

10.0 out of 10, Exceptional, (1)
Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate
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 Lenox?
You deserve a break, and a resort is the perfect place to find all the services and amenities you need for a relaxing trip to Lenox. One of the comfortable resorts in the surrounding area might be just what you’re searching for, whether you’re hoping for a luxurious suite, shopping possibilities, or activities for the kids.
What's the best resort in Lenox?
Here are our top-rated resorts near Lenox: SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires! - Ski resort right by Jiminy Peak Mountain Resort. 13.8 mi (22.2 km) from Lenox. Has ski-in/ski-out access, a fitness center, and beach sun loungers. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 13.7 mi (22.1 km) from Lenox. Enjoy the ski-in/ski-out access, fitness center, and garden. All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx. - Only a 5-minute walk from Jiminy Peak Mountain Resort. 13.8 mi (22.3 km) from Lenox. 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. 13.8 mi (22.3 km) from Lenox. Access to a fitness center and a hot tub.
What can I do in Lenox?
Travelers enjoy the cultural offerings in Lenox, and have good things to say about its museums and live music venues. Check out the interesting exhibits at Ventfort Hall Mansion and Gilded Age Museum and Berkshire Scenic Railway Museum, or catch the latest production at Shakespeare and Company or Tanglewood Music Center. For more to see in the area, you can spend time at Wyndhurst Golf & Club or The Mount.
What's the seasonal weather like in Lenox?
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 Lenox 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 Lenox?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 4.7 mi (7.6 km) away from the city center. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.8 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.