Vacation rentals in Stephentown

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Top-rated vacation rentals in Stephentown

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Superhost

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

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, 186 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!

Guest favorite

Cottage in New Lebanon

4.95 out of 5 average rating, 193 reviews

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and table.

Guest favorite

The image displays the welcoming sign of the Stephentown Hotel, featuring the hotel's name prominently. Surrounding the sign are colorful flowers, adding a touch of nature. In the background, the hotel building and nearby utility poles are visible, indicating its location along the road.

Apartment in Stephentown

4.83 out of 5 average rating, 66 reviews

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Welcome to the historic Stephentown Hotel! We are located minutes away from Jiminy Peak Ski Resort in the world famous Berkshire Mountains! Right on the NY / MASS border in beautiful Stephentown. Surrounded by nature and serenity. Beautiful 2 bedroom apartment on the 1st floor with a private entrance. We have (x2) fire pits, BBQs and old fashion popcorn machine on site! Every stay includes bottles of water, granola bars, oatmeal packets, coffee and tea! Parking right in front.

Guest favorite

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

4.89 out of 5 average rating, 164 reviews

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.

Top guest favorite

A wooden sign with the text 'BITTERSWEET FARM' is displayed prominently. Below the sign, a flower bed contains vibrant orange and yellow marigolds, adding a touch of color to the entrance. The surrounding grassy area is well-maintained, enhancing the welcoming appearance of the farm.

Farm stay in Pittsfield

4.99 out of 5 average rating, 221 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Top guest favorite

A colorful circular rug with a vibrant pattern is placed on a smooth bamboo floor. Natural light highlights the textures of the space, while a wooden staircase leads into the studio apartment. The overall layout showcases an inviting and dynamic atmosphere.

Apartment in Troy

4.93 out of 5 average rating, 443 reviews

Stunning studio in the heart of Troy: Raven's Den

Raven's Den is a large studio apartment with a queen sized bed, full kitchen, and an extra-deep bathtub. It is an open plan room that can be configured as needed, featuring two "aerial silk" hammocks that double as swings. It's in the heart of Downtown Troy, close to RPI, EMPAC, The Troy Music Hall, The Farmers Market, and the Takk House. Whether you need a cozy romantic getaway or simply a clean, fresh, place to lay your head, Raven's Den could be for you.

Guest favorite

A spacious outdoor seating area is situated under a wooden canopy, featuring multiple sectional sofas arranged around a central fire pit. Lush greenery surrounds the space, providing a serene atmosphere. The flooring consists of natural wood, enhancing the connection with nature.

Cabin in East Nassau

4.99 out of 5 average rating, 105 reviews

Artistic Blue Cabin with private creek and forest

Our wood cabin is located in a secluded area on 5 acres of forest and a creek flowing through the property that you see from every room. Newly renovated, our cabin is finished with refined colonial details and decorated with furniture from all over the world. Enjoy a morning coffee with a view of the creek by the wood burning stove or take a hike through our 5 acres of backyard forest. This property is the perfect escape.

Superhost

A wooden deck with a railing features flower pots at each end. An umbrella provides shade over a spot for seating. The section below the deck includes a stone path leading to the yard, framed by greenery and trees in the background.

Apartment in New Lebanon

4.78 out of 5 average rating, 18 reviews

A Sacred Place

A place that has a history of love. It’s cozy and it’s on beautiful family land in a central location . You can enjoy all four seasons here and all kinds of interests . With near by activity’s including skiing, hiking, lakes , fishing , horseback riding, museums, farmers markets, health and Yoga retreat center, and much more! Great Market , a couple cafes and restaurants right in town and plenty more.

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 green, spacious yard features two lounge chairs positioned near a fire pit, surrounded by lush grass and vibrant flowering plants. The farmhouse stands in the background, complemented by a rustic barn and mature trees enhancing the natural setting.

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!

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Other great vacation rentals in Stephentown

Guest favorite

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

4.95 out of 5 average rating, 226 reviews

Barn Stay at Shadowbrook Farm

MarthaRating, 5 stars4 weeks ago

The place is private with nice outdoor and indoor space, well outfitted. I wish we had had more time there.

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!

Top guest favorite

A charming two-story building is nestled in a snowy landscape, surrounded by tall trees covered in frost. Soft light glows from the windows, and a path leads to the entrance, highlighting the tranquil winter setting.

Guesthouse in Pittsfield

4.96 out of 5 average rating, 79 reviews

The Nest at Birdland

MichelleRating, 5 stars2 weeks ago

The Nest was a great spot for us to rest and recoup before our NEYC day! Mary was easy to work with, communicated well, and provided a great space with so many thoughtful extras!

Top guest favorite

A charming cabin exterior is shown, featuring dark wooden siding with orange trim around the windows and door. The sloped metal roof adds a rustic touch, while a small porch light is visible beside the entryway. Lush green grass surrounds the cabin, offering a serene setting.

Home in Stephentown

5 out of 5 average rating, 15 reviews

Berkshire Cabin

SolomonRating, 5 stars8 months ago

Avi's little house is situated on a peaceful property with a modern interior. It provides more than a standard hotel, featuring high-end appliances such as a Philippe Starck bigot, a Wolf range, a two-drawer dishwasher, and more. We had a wonderful stay at Avi's place and may consider returning in the future.

Top guest favorite

A serene outdoor seating area features three wooden Adirondack chairs arranged around a circular fire pit, set on a grassy expanse. Lush greenery from surrounding trees and ferns creates a peaceful, natural backdrop.

Vacation home in Stephentown

4.96 out of 5 average rating, 23 reviews

Quiet, peaceful wooded setting.

AshleyRating, 5 stars4 months ago

We had an incredible stay at Allison’s listing. Allison was easy to communicate with and very responsive. She was super helpful and accommodating. One of the nights there was a snow storm and the roads were bad so she even offered to bring over breakfast in case we didn’t have anything!! The location was amazing. It was easy to find and less than 15 minutes to Jiminy peak mountain for skiing. The house was clean/ cozy and had everything that we needed. I would highly recommend this Airbnb and would stay here again!

Cabin in Stephentown

4.81 out of 5 average rating, 21 reviews

Cabin Nestled in the Pines (New Arcade Machine!)

DanRating, 5 stars2 weeks ago

Georgianna's place was just what I was looking for. Rustic, secluded, and reasonably priced. Kitchen cookware was lacking a little bit, only a few stainless pans which can be a bit difficult to cook on, but that seems to be pretty typical with short term rentals. Overall everything was just as advertised and I would stay again.

Farm stay in Adams

5 out of 5 average rating, 4 reviews

Berkshires/Pet Friendly farm stay w/mountain views

SarahRating, 5 stars1 week ago

We had a great week full of hiking at Mt. Greylock and walking the local rail trail with our pups! Jessica’s place was a perfect touch down for everything we wanted to do. The camper felt private and cozy, a perfect place to relax and view beautiful scenery from the field. Getting to see the horses was a plus and our dogs loved hanging in the back yard. The camper was clean, comfortable and Jessica was very accommodating, making sure we had everything we needed! This is a place we would definitely come back to if we are in Adams again!

Guest favorite

A private hot tub is showcased on a wooden deck, surrounded by lush greenery. Soft blue lighting is reflected in the water. Two outdoor chairs are positioned nearby, and solar-powered string lights cast a warm glow over the area. The tiny house's glass wall is visible in the background.

Tiny home in Haines Falls

5 out of 5 average rating, 7 reviews

Romantic tiny Pod for two/HotTub/LakeView/FirePit

MaryoryRating, 5 stars6 days ago

We really enjoyed these days... the space is great, comfortable, cozy, with details that make it very special... everything is very well maintained and impeccable... congratulations on such a great place...

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Vacation rentals in Stephentown

Top-rated vacation rentals in Stephentown

Vacation rentals for every style

Popular amenities for Stephentown vacation rentals

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