Vacation rentals in Bentley Brook

4.86 out of 5 average rating, 290 reviews

A vintage coffee grinder is mounted on the wall next to a retro metal sign that reads 'Steaming Absolutely Fresh Hot Coffee.' The sign features bold red and blue lettering, complementing the rustic charm of the cabin.

Cabin in Stephentown

Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

4.85 out of 5 average rating, 41 reviews

A Keurig coffee maker is positioned on a granite countertop, accompanied by a two-tier wire basket holding a variety of coffee and tea pods, sugar packets, and creamers. The kitchen area is designed for easy beverage preparation.

Condo in Hancock

All-season Berkshires ski resort condo - Sitzmark

Stay at the Jiminy Peak mountain resort near renowned museums, music, dance and theater in the beautiful Berkshires. You'll be steps from swimming, hiking, aerial adventures and thrill rides. Meals are easy with two resort restaurants, a country store and a fully equipped kitchen. Spend your days at Tanglewood, Hancock Shaker Village, Mass MoCA and other nearby attractions. Then relax on the deck or in front of TVs in each room. Return for skiing in the winter with a fireplace for extra warmth.

4.88 out of 5 average rating, 185 reviews

A cozy outdoor seating area is highlighted by a stone fire pit, with flames dancing above a bed of volcanic rocks. In the background, a high-definition TV displays a sports event. Barstools and a wooden structure suggest a welcoming spot to relax.

Apartment in Petersburgh

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Space is 14 x 28 feet and includes living/dining/work space, bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed with pull out twin mattress. High def TV, wifi, private deck, kitchenette has mini fridge, microwave, toaster oven, hot kettle for tea and and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

4.89 out of 5 average rating, 188 reviews

A gentle stream flows through a wooded area, surrounded by trees with bare trunks and patches of moss-covered rocks. Fallen leaves cover the ground, and the sound of flowing water is evident in this serene natural setting.

Cottage in Williamstown

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 pull out couch.. Dog friendly for up to 2 dogs .More than one dog will have to be an additional fee of 50.00 each pet. My cottage sits on 13 privately owned acres. Partially fenced in.3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!

4.91 out of 5 average rating, 92 reviews

A detailed trail map displays the skiing and snowboarding routes available at Jiminy Peak. Color-coded paths represent varying levels of difficulty, while icons indicate peak locations, lift systems, and amenities. The surrounding mountainous landscape provides context for the trail network.

Townhouse in Hancock

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

5 out of 5 average rating, 19 reviews

Townhouse in Hancock

Serene+Stylish Mountain Retreat

Our beautifully-designed, comfortable, much-loved townhome is great for families or friends wanting an escape to the Berkshire mountains. Located up the hill from Jiminy Peak Village Center, the home has 4 bedrooms over 3 floors, an open plan living space, updated kitchen, family room, and new deck. A short walk to the slopes in winter and use of Jiminy Peak resort pools in the summer make it a year-round destination. Book your stay and find out why once you are here, it’s so hard to leave!

5 out of 5 average rating, 4 reviews

Apartment in Hancock

1st Floor Mountain View Suite Ski On/Off At Jiminy

You want to pop out of bed, walk down hall, and be right on the mountain This 1BR 1 BA Ground Floor Unit Charming Mountain Decorated Suite right by the entrance features a king bed in the master bedroom, plus a fold out queen sofa bed in the living room. The kitchen comes complete with all your needs, incl Keurig, pots, pans, etc. The unit is equipped with board games , along with smart TVs that have all your favorite shows . The Inn amenities are yours including heated year round pool

5 out of 5 average rating, 11 reviews

The image depicts a charming blue house surrounded by a serene winter landscape. Snow-covered ski slopes rise in the background, with ski lifts visible along the mountainside. Leafless trees frame the scene, creating a peaceful atmosphere in a snowy setting.

Apartment in Hancock

Artsy loft near MassMoCA with pool and hot tubs

This ski-in/ski-out loft at Jiminy Peak offers all of the amenities you could ever possibly ask for! A spacious 1 bedroom loft that sleeps up to 4 (1 Queen Bed, 1 Pullout Couch) is stylish and comfortable. We are the new owners and we are regularly updating the furniture and decor. A full kitchen, full bathroom with tub, ski locker / equipment storage, laundry in unit, dedicated parking spot, access to 2 pools and 2 hot tubs, a sauna, skiing, mountain cart, ropes course, and more!

4.96 out of 5 average rating, 24 reviews

A snow-covered building stands prominently against a backdrop of a frosty mountain slope. Softly shaped snow drapes over the surrounding trees, while the mountain, lightly dusted with white snow, is visible in the distance under a clear blue sky.

Vacation home in Hancock

Ski in/Ski Out - Building 1 Condo at Jiminy Peak

Book today and spend your ski days only steps from the lift! Get first tracks or even night ski from this one bedroom condo in Building 1 at The Country Inn at Jiminy Peak. Private parking, kitchenette, and all of the comforts of home. Visit any season to explore this beautiful Berkshire mountain. Enjoy private, gated parking, walk to the country store to get essentials, and even rent equipment right at the mountain. A family-friendly condo with food options for all.

4.94 out of 5 average rating, 32 reviews

An aerial view captures the expansive Jiminy Peak Resort, showcasing a snow-covered landscape dotted with trees and ski slopes in the background. The modern condominium complex sits prominently in the foreground, with parking spaces visible in front and mountain trails leading into the distance.

Home in Hancock

Bougie B’s Mountainside Getaway

Escape to our updated 2-bedroom, 2-bath condo at Jiminy Peak! Perfectly situated for the ski season, you'll enjoy quick access to both the slopes and apres ski. After a day on the trails, unwind at nearby restaurants like Christianson's Tavern or Bluebird & Co, offering top notch local eats. Bougie B's features updated amenities and that perfect touch of class to make you feel special. Come experience the beauty of the mountains today—your perfect escape awaits!

4.97 out of 5 average rating, 38 reviews

An aerial view captures the verdant landscape surrounding Jiminy Peak, showcasing ski trails seamlessly blending into the dense greenery of the mountains. Below, a collection of buildings is positioned within the valley, bordered by expansive parking areas and offering convenient access to outdoor activities.

Apartment in Hancock

Ski-InSki-Out Loft Lift&MT.Views

This ski-in, ski-out loft is located right at the base of the mountain in the Thatcher Lodge in the heart of the village at Jiminy Peak. Unmatched access to all of Jiminy Peak’s year-round activities. Skiing, mountain biking, hiking, tennis, swimming, fall foliage leaf peeping, shops, restaurants and the Mountain Adventure Park including the famous Mountain Coaster, Alpine Super Slide, Euro Bungy Trampoline, Soaring Eagle, Giant Swing, and climbing wall.

4.91 out of 5 average rating, 23 reviews

The exterior of a large light gray building is featured, displaying a covered entrance with stone accents. A wide staircase leads to the entrance from the parking area, complemented by a decorative railing. The sky is overcast, creating a calm ambiance.

Condo in Hancock

Large one bedroom, two full bath, full kitchen

Located in the heart of Hancock's premier ski-resort, Jiminy Peak this lovely appointed self contained apartment is ski on, ski off the 45 runs of the mountain. Perfect for a cozy Fall getaway to leaf peep all of the beautiful Berkshires. Close to Williamstown, North Adams, Lee, Lenox, Pittsfield and more. This is a year round spot with loads of activities. Pool, jacuzzi, exercise room and two restaurants are on site.

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Other great vacation rentals in Bentley Brook

4.83 out of 5 average rating, 12 reviews

A clear blue sky stretches above a tranquil swimming pool surrounded by lush green trees. A bowl of fresh raspberries and slices of kiwi is set on a table near the pool, with a distant view of a serene house on a hillside.

Home in Hancock

Lovely Home in the Berkshires

ElizabethRating, 5 stars3 months ago

We had a great stay. Toni was very responsive and the location is super close to the mountain.

An outdoor deck is presented with a large wooden table surrounded by chairs. Colorful cushions add comfort, and potted flowers brighten the space. Soft string lights hang above, illuminating a hammock and lounge chairs nearby, all set against a backdrop of lush greenery.

Guest suite in Hancock

4.81 out of 5 average rating, 180 reviews

Cozy apartment near Jiminy Peak

KatieRating, 5 stars3 months ago

We loved staying with Naren! She was very accommodating and has a beautiful home:) Highly recommend and would love to return!

Vacation home in Williamstown

A wooden porch features two Adirondack chairs and a small footrest, all in a rich brown hue. Natural light filters through the nearby windows, illuminating the wooden flooring and the inviting setting. A storage box is positioned beside the chairs.

4.98 out of 5 average rating, 96 reviews

ALL welcome: Lovely 1 BR studio, Berkshires beauty

SamRating, 5 stars3 months ago

The hosts were very helpful in general, and responded immediately to take care of a minor issue we mentioned. The studio in the barn is clean, comfortable, and well set up. It's a great spot for 1-2 people. The only minor complaint (which is out of the host's control) is that my wife and I use Verizon, and the studio was a dead zone for cell service for us [when we needed to make a call, we 'solved' this problem by walking down the driveway towards the road, where we got signal]. Wi-Fi in the studio worked great for computer use and streaming, so that is not an issue, just Verizon cell service. We had a great stay overall!

Home in Hancock

4.88 out of 5 average rating, 8 reviews

Snowdrop Lodge: Beautiful Condo at Jiminy Peak

BrianRating, 5 stars5 months ago

It was great to be on the property at Jiminy Peak walking distance to the lodge and mountain. Place was adorable. Perfect for our family of four. They had garbage bags, soap and all the necessities. Would definitely stay there again.