Vacation rentals in Cherry Plain

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Top-rated vacation rentals in Cherry Plain

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Superhost

An old-fashioned cedar hot tub is positioned on a wooden deck, surrounded by trees displaying autumn foliage. The peaceful outdoor setting offers a serene atmosphere for relaxation.

Cabin in Stephentown

4.85 out of 5 average rating, 301 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.

Guest favorite

A charming blue cottage with a wooden fence is showcased, featuring an American flag mounted on the front. The entrance includes a door framed by two windows, and a rustic fence leads to the path, surrounded by autumn leaves and forest greenery.

Cottage in Williamstown

4.89 out of 5 average rating, 194 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!

Guest favorite

A detached red barn is surrounded by a grassy yard, with patches of snow visible on the ground. The property features a gravel driveway leading to the barn's double garage doors. Mature trees line the background, offering a natural setting.

Guesthouse in Lenox

4.9 out of 5 average rating, 277 reviews

The Coach House | Modern 2BR Loft + Views & Pool

Restored coach barn with 25-ft cedar ceilings, skylights, and mountain views—part of House on Golden Hill, a historic Lenox farmhouse compound. This airy 2BR + loft retreat blends rustic charm with modern ease. Enjoy a full kitchen, cozy living space, and outdoor area. Set beside a stream with seasonal pool access, it’s perfect for families, couples, or creative escapes. Centrally located and just minutes to downtown Lenox, Tanglewood, and trails—your Berkshires base for rest and inspiration.

Top guest favorite

A spacious bedroom features a large queen bed with a white duvet and decorative pillows. Two sets of French doors open to an outdoor view, flanked by soft curtains. A cozy seating area with a light-colored sofa adds comfort, illuminated by natural light from the windows.

Guest suite in Valatie

4.98 out of 5 average rating, 259 reviews

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

Guest favorite

A wooden structure with a deck extends into the greenery, framed by tall hop poles. The building features a large front porch, inviting outdoor seating, and an entrance accentuated by surrounding trees and a grassy area leading up to it.

Apartment in Petersburg

4.89 out of 5 average rating, 201 reviews

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Open space includes living/dining/work space & bedroom; bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed (extra twin mattress beneath). HD TV, wifi, private deck, kitchenette with mini fridge, microwave, toaster oven, hot tea kettle 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

The entrance to a Hobbit house is framed by lush greenery and natural stone. A curved, grassy roof merges with the surrounding trees, while a stone pathway leads to the large wooden door. Decorative lanterns are positioned above the entrance, enhancing the rustic charm.

Earthen home in West Sand Lake

4.97 out of 5 average rating, 210 reviews

The Hobbit House at June Farms

Enjoy 120-acres of beautiful farmland while you stay in your very own Hobbit house! Nestled in the hills of Hudson Valley, June Farms is a gorgeous animal sanctuary. During your stay, you will be able to meet our Shire horses, Scottish highland cows, Gloucestershire spotted pigs, Nigerian dwarf goats, many chickens and ducks! From June 1 - Labor Day, the bar & restaurant is open most days for you to enjoy (check our calendar to be sure). We look forward to meeting you!

Superhost

A well-appointed bedroom features a spacious bed adorned with a patterned quilt. Natural light streams in through large windows, complemented by dark curtains. A stylish dresser and a cozy red armchair are present, creating a comfortable and inviting setting.

Cabin in Stephentown

4.68 out of 5 average rating, 31 reviews

Cabin Nestled in the Pines (New Arcade Machine!)

Step back in time and remember when life was less complicated. Come relax in this vintage full house on private dead end street. The setting is peaceful and surrounded by hemlocks. Two bedrooms and two baths and a full size deck. Entertainment includes WiFi and a TV with roku and Netflix. There are many fun activities in the area, including multiple ski resorts and beautiful hiking trails. Minutes from the Berkshires and also close to Vermont and the Capital region.

Top guest favorite

A canvas tent is set on a wooden deck, featuring a spacious bed with natural linens and decorative elements. Two wooden Adirondack chairs are positioned on the deck, facing the entrance. Nearby, a wood stove and a small table are included for added comfort.

Farm stay in Johnsonville

4.99 out of 5 average rating, 242 reviews

Hide-a-way at Graceful Acres Farmstay

Enjoy the grace of a historic family farm in the heart of eastern NY. Let the cool, fresh air and sounds of the outdoors start your day. Fill your time with a hike across our 440 acre farm then spend time with the animals and learn more about regenerative farming during a scheduled farm tour. Graceful Acres Farmstay is situated an hour south of the Adirondack State Park and within 35 minutes of Saratoga Springs, Albany, Troy, NY and Bennington, VT.

Top guest favorite

A garden scene is presented with a wrought-iron chair nestled among frosted pink and green sedum flowers. A leafless tree stands in the background, framed by autumn foliage. Rolling hills are visible beyond the landscaped area, hinting at the surrounding natural beauty.

Vacation home in Williamstown

4.98 out of 5 average rating, 110 reviews

ALL welcome: Lovely 1 BR studio, Berkshires beauty

Come as you are - we welcome ALL visitors. Relax and soak in your surroundings in this new 1 bedroom vacation spot. Part of a barn conversion, the space is clean and bright and ideally located for those exploring all the Berkshires has to offer. Perfect for an individual or couple looking to escape to a serene and beautiful setting - a stream abuts the property and hiking/snowshoeing trails are accessible out the front door.

Guest favorite

A charming cabin exterior features a wooden porch with a yellow door. Stone pathways lead to the entrance, surrounded by landscaped greenery. Natural lighting highlights the rich wood beams and inviting seating area, while vibrant foliage of the forest provides a serene backdrop.

Cabin in East Nassau

4.98 out of 5 average rating, 124 reviews

Design Lover’s Blue Cabin

Blue Cabin is a cozy, design-forward retreat between the Capital Region and the Berkshires. Enjoy vaulted wood ceilings, a forest-green kitchen, and a spa-style bath. Outside, unwind in the covered lounge with U-shaped sectional, charcoal grill, and TV—or explore the backyard, where a creek runs through and a seasonal flower garden blooms. Peaceful, private, and perfectly located for both rest and adventure.

Guest favorite

A vibrant red yurt is nestled among the trees, surrounded by autumn foliage. A wooden platform supports the yurt, while a vehicle is parked nearby. A light plume of smoke is seen rising from the woodstove, indicating warmth inside.

Yurt in Stephentown

4.9 out of 5 average rating, 132 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!

Guest favorite

A comfortable living area features a sectional sofa and a single armchair arranged around a small metallic coffee table. A colorful area rug adds warmth to the space, while a lamp provides soft lighting. Exposed wooden beams enhance the architectural detail, and a door leads to the hallway.

Apartment in Williamstown

4.93 out of 5 average rating, 323 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.