Ski-in/Ski-out vacation rentals in Berkshire County

Find and book unique ski-in/ski-out homes on Airbnb

Top-rated ski-in/ski-out rentals in Berkshire County

Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A cozy bedroom features a spacious bed draped in a soft, dark blanket. The walls are adorned with a captivating array of framed artwork, showcasing various styles. A bedside table holds a lamp, and a curtain partially covers a window, allowing natural light to filter in.

Place to stay in North Adams

4.93 out of 5 average rating, 259 reviews

Freemans Grove Benevolent Society Walk to MoCA

Welcome to the Freeman's Grove Benevolent Society! Artist's apartment/gallery with kitchen, bath, one bedroom, and a sleeping nook. It is an open floor plan, for heating purposes there are curtains (no doors) on the bedroom and sleeping nook. Sleeps 4 people comfortably. The walk from MASS MoCA to the house is flat except the last block which is STEEP! The apartment is a flight and a half off the street, so be prepared for some stairs. A truly unique apartment and cabinet of curiosities. #fgbs

Top guest favorite

A panoramic view captures the snowy landscape from the condo, showcasing ski trails on the mountains in the background. The foreground features a plaza with chairs arranged around a fire pit, with skiers and snowboards visible along the paths.

Condo in Hancock

4.98 out of 5 average rating, 47 reviews

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2

Ski-in,ski-out! Unbeatable location for all seasons! Closest condo at JiminyPeak to the slopes and lifts. Located right at base of Mt. in JJ’sLodge in the heart of JiminyVillage. Mere steps to BerkshireExpress HighSpeed 6pack! Amazing pano views of the slopes surround. Designated pkg space in owner’s pkg lot. Unmatched access to all JP’s year-round activities. Skiing,MtBiking,hiking,tennis,swimming,fall foliage leaf peeping, shops,restaurants,MtAdventurePark w/ famous MtCoaster&AlpineSuperSlide.

Top guest favorite

A spacious living area features a large sectional sofa adorned with textured cushions and a sleek coffee table. Natural light floods through tall windows, illuminating the open-plan layout, which seamlessly connects to the dining area with a wooden table and high-backed chairs.

Townhouse in Hancock

5 out of 5 average rating, 26 reviews

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!

Superhost

A cozy living area features a tall Christmas tree adorned with lights and ornaments next to a glass-top coffee table. A fireplace with built-in decor sits beneath a mounted television. Velvety blue chairs complement an orange accent pillow on the nearby couch, surrounded by large windows with sheer curtains.

Apartment in Hancock

4.76 out of 5 average rating, 17 reviews

Artsy loft surrounded by fall foliage with hot tub

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!

Superhost

A bright living area features a soft gray sofa with decorative pillows, complemented by a plush area rug. A coffee table holds decorative items, and a seating area includes a cozy recliner. Large windows allow ample natural light while providing views of the outdoors.

Apartment in Hancock

4.9 out of 5 average rating, 21 reviews

Gorgeous Zen Must-See Suite At Jiminy Country Inn

This is the MOST UNIQUE suite in the Berkshires, specially designed for an incredible experience. The Master Bedroom Features a King Bed, and the main room has a Queen Sofa bed for extra room. This Peaceful Suite features a luxurious massage chair, waterfall, color changing lights, Ionic Salt Diffuser, Zen Garden, and tons of surprises you just have to see. There is even a professional massage table in the closet! The King BR comes with Oil Diffuser, Sound Machine, Bamboo bedding.

Guest favorite

A pathway lined with lush greenery leads to a bungalow with a screened-in porch, featuring outdoor seating. The soft sunlight filters through the foliage, creating a serene entrance to the welcoming space.

Home in Williamstown

4.89 out of 5 average rating, 224 reviews

Hollywood Bungalow in the Berkshires #C0191633410

Cool Cozy Rustic Country Bungalow with Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Cable & Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

Guest favorite

The exterior of The Country Inn is shown, featuring a covered entrance with a sloped roof and decorative columns. Lush greenery and flowering shrubs frame the front, while the building's muted tones complement the natural surroundings. Nearby parking spaces are visible under an overcast sky.

Vacation home in Hancock

4.96 out of 5 average rating, 26 reviews

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.

Guest favorite

The front of the house is framed by lush greenery and a vibrant red maple tree. A welcoming red staircase leads to the entrance, while large windows allow natural light to illuminate the interior. The roof is partially covered with clouds, enhancing the outdoor serenity.

Home in Otis

4.92 out of 5 average rating, 163 reviews

The Pinnacle House at Otis Ridge Ski Area!

Otis is the best town for a visit to the Berkshires. It is close to all the places you would want to visit like Jacob's Pillow, Tanglewood, Norman Rockwell Museum to start with. It is also close to hiking trails, swimming, shopping and great restaurants. This wonderful three plus bedroom home is located on the backside of Otis Ridge Ski Area. Wake up and take a walk on the ridge or just sit outside and have your morning beverage with the woods surrounding you.

Superhost

Home in Hancock

4.93 out of 5 average rating, 30 reviews

Family Lodge at Jiminy Peak - Pools & Adventure

Escape to the Berkshires this summer in our spacious 4BR/3BA townhome at Jiminy Peak! Perfect for families, with 2 living rooms, a fully equipped kitchen, and a large Trex deck with mountain views. Enjoy resort perks like outdoor pools, tennis, hiking trails, mountain coaster, and ropes course—all just steps away. With plenty of space and nonstop adventure, it’s the ultimate summer getaway for families and friends!

Guest favorite

A living area features a beige sofa with cushions, positioned beside a dark wood coffee table. Natural light enters through a large window with tan drapes, offering a view of grassy landscaping. A simple lamp stands next to the sofa, enhancing the cozy ambiance.

Condo in Hancock

4.9 out of 5 average rating, 71 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.

Superhost

An old agricultural tool sits in a grassy field, its wheels complementing the expansive landscape. In the background, vibrant hues of sunset illuminate the sky, casting a soft glow over the lush green foliage and distant hills.

Guest suite in Lee

4.73 out of 5 average rating, 204 reviews

Berkshire Charm w/ Panoramic views

This is a new beautiful and tastefully renovated building high on October Mountain that offers panoramic views and amazing sunsets over the Berkshires. This intimate space has walking and cross-country ski trails, fire pit, gardens, decks, streams and more. While having a remote and rural feel you are located in the heart of Berkshire culture only minutes form Lenox, Lee and Great Barrington MA.

Guest favorite

The interior of the renovated studio cabin is seen from the kitchenette area. A bed, adorned with a patterned coverlet, is framed by a folding screen featuring floral and landscape designs. Artwork hangs on the walls, adding character to the warm space.

Guesthouse in Becket

4.92 out of 5 average rating, 280 reviews

Country Cabin

Lovely private country setting, air conditioner. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. The space is for 2 adults but I'm flexible, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.