Hancock, Massachusetts
Wyndham Bentley Brook

Wyndham Bentley Brook Vacations, Resorts, Rentals, Suites and Getaways

  • What We Love

      • You’ll love the indoor/outdoor pool and the spacious gazebo hot tub.
      • Bentley Brook has a cool mini cinema with real, comfortable theater chairs!
      • Jiminy Peak Mountain Resort is right next door, providing your family with a multitude of activities, a small store, and restaurant.
      • This great location gives you easy access to skiing and other outdoor adventures.
      • You’re also super close to the natural haven of The Berkshires, so you can hike, picnic, and relax in these gorgeous surroundings without a huge hassle!
  • Description

    • Nestled among the Berkshire Mountains, you will find a true New England treasure; Wyndham Bentley Brook. Located a mere 200 feet away from the premier Jiminy Peak Mountain Resort puts you in position to take part in the area’s best skiing and snowboarding. After a full day on the slopes, warm up and relax in cozy studio, one- and two-bedroom units. Rooms here showcase both scenic mountain and valley views, and are filled with all the comforts and conveniences of home. All units feature a full kitchen; equipped with a stove, oven, dishwasher, microwave, and all the cookware needed to put together a private feast. Well laid-out suites provide generously-sized bedrooms and living rareas; two bedroom units even feature an in-suite washer and dryer.


      The resort boasts both indoor and outdoor pools, and hot tubs for your full relaxation. Tennis courts, exercise equipment, sauna, and picnic and BBQ areas are offered for your enjoyment as well. Children will be entertained by the “Play Days” activities program and game room. Summer presents a wealth of activities as well, as Jiminy Peak transforms its ski slopes into mountain bike trails, a ropes course, and even a mountain coaster. Stay at Wyndham Bentley Brook, and enjoy the Berkshires in comfort and style.


    • Tripbound Traveler FavoriteTake to the hills for a romantic moonlit hike at the historic Hilltop Orchards. Home to the award-winning Furnace Brook Winery, the farm features 200 acres of the most incredible views and trails in all of the Berkshires. The always popular “Full Moon Hike & Bonfire” runs year round, according to the lunar cycle. The fee for this tour is $10 per adult, and includes a 1-1/2 hour interactive hike that finishes off with wine and cider samples by the bonfire. Tour times vary according to the time of year, and reservations are highly recommended due to limited space. If you don’t happen to be in town for a tour, don’t worry because Hilltop Orchards has miles of trails designed for hiking, cross-country skiing, and snowshoeing.

  • Amenities

    • Unit Amenities

      · Cable TV
      · DVD player

      · Fully equipped kitchen - and even wine glasses!

      · Air conditioning

      · Balcony / deck (excludes studio units) 

      · Washer and dryer (2 BR Deluxe units)

      · Sofa bed

      · Whirlpool tub (2 BR Deluxe units) 

      · Hair dryer

      · Iron and ironing board

      · Wireless Internet access


      Resort Amenities

      · Indoor swimming pool

      · Outdoor swimming pool

      · “Play Days” activities program

      · 3 Tennis courts

      · Exercise equipment

      · Laundry facilities*

      · 1 Indoor & 2 Outdoor hot tubs

      · Game room

      · Picnic / BBQ area

      · Tour desk

      · Video rentals*

      · Kid's programs

      · Sauna


      Please note that some amenities are made available on a seasonal basis and at an additional charge.* 


      Daily housekeeping is not included and may be added for a nominal charge.


      Check In: 4:00 p.m., Check Out: 10:00 a.m.


      Local Activities

      · Full Moon Hike & Bonfire

      · Furnace Brook Winery

      · Hancock Shaker Village

      · Jiminy Peak

      · Norman Rockwell Museum

      · Hilltop Orchards

      · Berkshire Museum

      · MASS MoCA Museum of Contemporary Art

      · Horseback riding

      · Mountain biking

      · Water skiing

      · Boating

      · Shopping

  • Suite Options

    • 2 Bedroom Deluxe

      Two Bedroom Deluxe unit features a varying bed layout, two bathrooms - whirlpool tub in Master, washer and dryer, and private balcony or deck. Full kitchen with coffee and tea maker, microwave, refrigerator, oven, dishwasher, stove, toaster, cookware, flatware. Convenient comforts include cable TV, DVD player, hairdryer, AM/FM alarm clock, iron and ironing board, and complimentary wireless Internet. Max occupancy: 8, sq. ft. varies

  • Rate Schedule

    • Promotional codes and seasonal sale prices not reflected.
      Use Instant Quote feature to apply any discounts.
      2 Bedroom Deluxe
      Reservation fees not included.
  • Map

    • 1 Corey Road, Hancock, MA
  • Resort Reviews

    • Simple, clean and convenient.
      Posted by Jeff R. on 03.28.2019
      We had a great time and the resort was very convenient for families! Ski in, ski out!
      Posted by Craig L. on 02.03.2019
      Bentley Brooke Wyndham is terrific! And booking through Tripboubd is easy & affordable. Highly recommend.
      Posted by Lara D. on 01.20.2019
      The ski in ski out is very convenient and the 2 bedroom deluxe is very spacious.
      Posted by Earnest L. on 01.04.2019
      We had a great 5-night stay in a 2 bed, 2 bath that had plenty of space for the six of us, plus a pullout couch we didn't even use. It was updated, clean, and the staff was very friendly. All amenities were there, including in-unit washer and dryer with detergent there for us to use. Loved the activities for the kids (such as making friendship bracelets and scented lip balm in the activity room) and the pool was perfect for our young kids. Jiminy Peak was awesome in the summer - kids had so much fun doing the ropes course, zips, mountain coaster, etc etc....and it was walking distance to get there! Overall great stay and highly recommend!
      Posted by Stephanie M. on 08.25.2018
      Well maintained. Pleasant staff
      Posted by Karen F. on 08.01.2018
      Staff is friendly and helpful, room was clean and very well stocked, and the amenities were great for the kids!
      Posted by Kathleen G. on 06.24.2018
      The Bentley Brook Resort was really clean, amazing amenities. I loved the indoor/outdoor pool and the fact that there was an adult only hot tub AND pool. 2 bathrooms, 2 bedrooms, and full kitchen were very useful. Unit was spacious and just the right amount of space/size for our trip. The setting was perfect and so easy to get to. All staff were so super friendly as well.
      Posted by Cheryl B. on 07.11.2018

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What Our Travelers Are Saying
Donna I
Jul 14, 2018
This was such an easy vacation to plan since Tripbound helped me every step of the way! Nicki was great finalizing my plans and putting in special requests! The room was much more affordable than on other sites. I would definitely use Tripbound again!
John C
Jul 11, 2018
Incredible communication. Easy to use website. A perfect company for helping plan a family vacation
Linda H
Jun 18, 2018
We have booked several trips with Tripbound. They are always very friendly and helpful, and their prices are great.
Sara McCaw R
Jul 19, 2018
Everything about this experience was perfect. From day 1 of booking to the last day when we were checking out of the resort, the whole process was seamless. The condo we stayed at in Sevierville, TN was spacious, the beds were amazing, the amenities kept our whole family entertained, and the location couldn’t have been better. I would highly recommend this rental to any family that is traveling. We will continue to use Tripbound for our future vacation accommodations. Thank you for making our vacation feel like home.