Vacation rentals in Cherry Plain

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Top-rated vacation rentals in Cherry Plain

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Superhost

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

4.86 out of 5 average rating, 290 reviews

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.

Top guest favorite

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

4.88 out of 5 average rating, 185 reviews

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.

Guest favorite

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

4.89 out of 5 average rating, 188 reviews

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!

Top guest favorite

The entrance of a light green house is shown, featuring a welcoming door with multiple glass panes. A wooden welcome mat lies at the foot of the door, while a pathway leads through a well-maintained grassy area beside it.

Guest suite in Williamstown

4.96 out of 5 average rating, 238 reviews

Berkshire Guest Suite

Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.

Top guest favorite

An electric cedar barrel sauna features smooth wooden benches along the curved walls. The interior is warmly lit, highlighting the natural wood grain. A compact heating unit is positioned centrally, providing a functional and relaxing ambiance for guests.

Cabin in Petersburgh

4.93 out of 5 average rating, 235 reviews

Cozy Retreat in the Trees

Time travel to 1958 in this architectural gem! This mid-century modern glass and wood cabin is 300 yards away from a charming small lake. The house is NOT on the lake itself, but it is surrounded by trees in a lovely secluded spot. The only heat is a wood stove... but there is a 4-person cedar barrel sauna in the woods that is electric. A classic 1952 Spartanette travel trailer serves as an extra bedroom. This is a true retreat for romance and adventure.

Top guest favorite

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

4.98 out of 5 average rating, 425 reviews

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!

Guest favorite

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

4.92 out of 5 average rating, 66 reviews

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.

Top guest favorite

A grassy area is surrounded by a variety of trees, creating a serene outdoor space. Several seating options, including benches and chairs, are arranged around a central wooden table. Potted plants add a touch of greenery, enhancing the relaxing environment.

Barn in Williamstown

4.97 out of 5 average rating, 301 reviews

Cozy barn apartment on the river

Private converted first floor barn apartment next to the Green River. Comfortable with unique furnishings and back door that opens to a riverfront covered patio. Sleeps 1-2 comfortably. Can accommodate 4 with the extra sleeper, tri-fold floor mattress, (Best for 1-2 smaller children). Private full bath. Great for 1-2 adults or a family with smaller children. It is on our property with a shared driveway.

Superhost

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

4.9 out of 5 average rating, 126 reviews

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!

Top guest favorite

A bathroom features a modern toilet positioned under a window, providing natural light. The gray tiled floor complements the neutral wall color. A toilet paper holder is visible nearby, along with a small waste bin and a metal shelving unit in the corner.

Apartment in Williamstown

4.94 out of 5 average rating, 304 reviews

COLD SPRING

Welcome to your peaceful Berkshire retreat. Originally a barn, this charming two-bedroom, one-bath apartment features a fully equipped kitchen, skylight-vaulted ceilings, and original wood beams. Just a short drive from Mount Greylock, Jiminy Peak, and the Williamstown Theatre Festival—surrounded by scenic hikes and great local dining, it’s the perfect home base for your getaway.

Top guest favorite

A white chicken stands near a basket of eggs, surrounded by daffodils. The setting includes a background of a variety of chickens and natural greenery, highlighting the farm's vibrant agricultural life.

Loft in East Nassau

4.99 out of 5 average rating, 181 reviews

Dog Friendly Farm

Welcome to The June Arthur Farm! This beautiful spot has a long agricultural history. It hasn't been in production for the past 40 years but we're slowly bringing it back to life. It's once again producing good, happy, Hudson Valley food: eggs, fruit, lamb, and beef. We hope you'll come visit us. Note for the skiers out there: We're 20 minutes from Jiminy Peak!

Top guest favorite

A gentle brook flows through a landscape adorned with autumn leaves. Tall trees line the banks, their foliage transitioning to various shades of gold and orange. Smooth stones are scattered in the water, and the ground is covered with a carpet of fallen leaves.

Guesthouse in Williamstown

4.96 out of 5 average rating, 184 reviews

Brookside Cottage

Drift off to the sound of a babbling brook outside the bay window in this cozy country cottage. Minutes from Downtown Williamstown, North Adams and Bennington, VT. We are about 20 minutes away from Jiminy Peak for downhill skiing. The trails behind our house are ideal for snowshoeing, nordic skiing, and snowman building.