Vacation rentals in Bentley Brook

4.86 out of 5 average rating, 290 reviews

A rustic cabin is nestled in a wooded area, featuring a bright red front door and a spacious deck. Surrounding the deck, lush greenery provides a natural backdrop, and a cozy seating area is visible on the porch. A fire pit with stones is situated in the foreground.

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!

5 out of 5 average rating, 5 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!

4.89 out of 5 average rating, 164 reviews

A quaint cottage is nestled among trees, featuring a welcoming front porch with several potted plants and outdoor seating. The light-colored exterior is complemented by blue accents on the chairs, while the wooden deck extends invitingly, creating a serene outdoor space.

Cabin in Cheshire

Private Paradise in the Berkshires

Your own private and romantic getaway behind a small orchard. A sweet running brook and outdoor shower! A short drive to all Berkshire cultural events -- Tanglewood, Jacob's Pillow, theatre festivals and more. Great dining nearby. Perfect for 2! Under COVID-19 regulations in Massachusetts, I am required to allow at least 24 hours between guests. It's a drag, but it is intended to keep us all healthy! Please forgive any inconveniences this might create in your trip plans.

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!

4.98 out of 5 average rating, 425 reviews

An inviting wood-fired Finnish sauna is presented with a circular wooden interior. A small stove, burning warmly, is visible along with benches along the walls. Natural light filters in through a glass door, creating a soothing atmosphere.

Home in North Adams

Steps to MoCA private house + SAUNA!

Tucked away on a hilltop oasis above MoCA (3 minutes by walk) the whimsically restored house is part of a private estate. 10 min drive to Williams College & Clark. Steps to downtown & restaurants. Your stay enables us to host refugee & immigrant musicians pro bono year-round. More info on @chasehillartistretreat Note: more dates are often available beyond what the calendar shows. Please don’t hesitate to inquire!

4.92 out of 5 average rating, 66 reviews

A spacious bed adorned with white linens and decorative pillows is positioned near large windows. Soft natural light filters through the curtains, highlighting the cozy atmosphere. A lamp sits beside the bed, contributing to the room's overall comfort.

Condo in Hancock

Jiminy Peak Country Inn - ski in/out condo MT view

Rent your very own condo in the Country Inn at Jiminy Peak Mountain Resort.This unit is just steps away from the entrance and your ski locker. Ski in/out and never have to move your car! Spectacular view of the mountain from your windows, close to all the amenities the resort has to offer. The resort offers a year-round heated pool, 2 hot tubs, a gym, fireplace lounge and restaurants. The perfect mountain escape.

4.9 out of 5 average rating, 126 reviews

A flowing stream is nestled among lush greenery, bordered by tall trees and dense foliage. Clear water glistens as it travels over smooth stones, with soft ripples audible in the serene environment.

Yurt in Stephentown

Off Grid Yurt Right By The Best of The Berkshires

This is an off grid yurt with a woodstove for heat and an off grid kitchen - no running water or electricity - water can be heated on the woodstove. You'll have a comfy bed and futon. We love it when it rains. Staying inside, listening to the rain on the yurt and playing games is a highlight of our trips there. Cooking outside and enjoying a campfire & toasting marshmallows is also fun!

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Other great vacation rentals in Bentley Brook

4.95 out of 5 average rating, 225 reviews

The spacious interior features high wooden beams and a stone fireplace at its center. Natural light fills the area through large windows, highlighting the open floor plan. A loft area is visible above, and comfortable seating arrangements support relaxation and gatherings.

Farm stay in New Lebanon

Barn Stay at Shadowbrook Farm

JenniferRating, 5 stars1 month ago

The space was beautiful, clean, and exactly as pictured! We enjoyed a weekend away and appreciated the local recommendations shared in the guide. We spent time exploring the farm, the surrounding area, and also were able to kick back and relax in the amazing property.

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

DougRating, 5 stars2 days ago

What a wonderful gem! My wife and I stayed here for a Williams College reunion. The rental is a wonderfully furnished barn in a gorgeous pastoral setting. Very comfortable! Nicely furnished with plenty of amenities. There’s a delightful breakfast place just down the road, and this place is perfect if you happen to be in the Berkshires and Williamstown.

5 out of 5 average rating, 31 reviews

A serene outdoor space is presented, featuring two wooden chairs positioned around a fire pit surrounded by gravel. A rustic wooden structure holds firewood nearby, while trees provide a natural canopy overhead, creating a secluded area for relaxation.

Camper/RV in East Nassau

The Hawk's Nest

ArsalanRating, 5 stars1 day ago

We had best time there! awesome host ! She was really kind in entire trip, we were there with our baby and she gave him toys & books ❤️ Everything was perfect and safe , Thanks to her

4.97 out of 5 average rating, 36 reviews

A tall stone tower rises against a bright blue sky adorned with fluffy white clouds. A gravel path leads through lush green grass, guiding visitors toward the monument. Trees are visible along the pathway, creating a natural frame for the scene.

Home in Williamstown

New Berkshire home - 3 bed, 2.5 bath w/views

MichaelRating, 5 stars3 weeks ago

2nd year staying there. Trina is great and as usual the house was perfect! we'll see you next year!