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Compare 26 Resorts in Lenox with updated reviews, rates, and availability.

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
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
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
1 Bedroom - Vacation Village in the Berkshires Resort - Hancock
Property grounds
1 Bedroom - Vacation Village in the Berkshires Resort - Hancock
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!"
1 Bedroom - Vacation Village in the Berkshires Resort - Hancock
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
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.
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!
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 Kemble- Built by a US Secretary of State in Lenox
The Kemble - a registered Great Estate
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (16)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
The Winthrop Estate - 12K SF 32 Acres
The Winthrop (1)
The Winthrop Estate - 12K SF 32 Acres
10.0 out of 10, Exceptional, (4)
"Everyone enjoyed the stay"
The Winthrop Estate - 12K SF 32 Acres
Amore Estate - beautiful room with many places to explore and relax in.
October MNT FARM!!
Amore Estate - beautiful room with many places to explore and relax in.
9.8 out of 10, Exceptional, (17)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
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: Canyon Ranch Lenox - 0.9 mi (1.5 km) from Lenox. Has a seasonal outdoor pool, a health club, and a steam room. 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. Cozy Cabin on resort property in Cultural Berkshires. Labor Day Sale! - Ski resort right by Jiminy Peak Mountain Resort. 13.8 mi (22.2 km) from Lenox. Amenities include ski-in/ski-out access, a fitness center, and beach sun loungers.
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. Discover the theater scene at Shakespeare and Company and Tanglewood Music Center, or take the whole family to The Bookstore and Berkshire Scenic Railway Museum. For more to see in the area, you can spend time at Ventfort Hall Mansion and Gilded Age Museum or Wyndhurst Golf & Club.
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.