Ski-in/Ski-out holiday rentals in Western Massachusetts

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

Top-rated ski-in/ski-out rentals in Western Massachusetts

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

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Top Guest favourite

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

4.94 out of 5 average rating, 277 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

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Guest favourite

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

4.94 out of 5 average rating, 398 reviews

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

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Superhost

A cozy living area features a dark gray sofa with decorative cushions, complemented by two wooden armchairs. A timber-framed window offers a view of the outdoors. A coffee table holds a small centerpiece, and vintage skis are mounted on the wall above the seating.

Home in Wilmington

4.85 out of 5 average rating, 144 reviews

MtSnow HotTub Pool Table AirHockey PingPong *Darts

Welcome to our ❄newly listed❄lodge style home! HOT TUB✅ Our home is located on private 2.6 acre lot with beautiful views of Mount Snow in the distance. Our home offers easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our home. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in southern Vermont!

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Guest favourite

A lakefront cottage is positioned among trees, with a spacious lawn leading down to the water. A newly installed dock extends into the lake, while various colorful kayaks and paddle boards are neatly arranged on the grass. The sun sets, casting a warm glow over the scene.

Home in Westminster

4.89 out of 5 average rating, 239 reviews

Lakefront, view of ski mtn, fireplace, sauna

Direct lakefront with panoramic views of Wachusett Mountain (#1 skiing in MA). In the summer, enjoy the kayaks, canoe, paddle-boards, motor boat. In the winter, cozy up next to the fireplace and enjoy a complimentary bottle of wine. In the fall, gaze upon the breathtaking foliage from the sunroom. Outdoor shower, dock, firepit, hammock, bike, washer/dryer, desk, sauna, dishwasher, linens, kitchen amenities. Our other lakefront house is down the road: www.airbnb.com/h/lakefrontmountainview

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Guest favourite

Condo in Dover

4.92 out of 5 average rating, 128 reviews

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna

Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

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Top Guest favourite

A serene lakeside scene features a plush chair by the water, where a golden retriever is comfortably resting. Lush greenery surrounds the lake, and a kayak is seen moored nearby, adding to the tranquil atmosphere.

Cottage in Newbury

4.95 out of 5 average rating, 253 reviews

Large Private Lake House

Spacious lake house with a private beach, directly on Lake Todd in Newbury, NH, located within the Lake Sunapee Region. Fish for bass, pickerel or swim/boat to one of the lake's three islands. Relax on the water or on one of the large decks overlooking the lake. Enjoy local outdoor activities such as hiking, biking, golfing, fishing & kayaking. Mt Sunapee ski area is only 10 minutes down the road. Enjoy ice skating and cross country skiing right out your door in the winter or cozy by the fire.

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Top Guest favourite

A peaceful scene reveals a winding road leading through a residential area with well-maintained homes. Snow-covered mountain slopes are visible in the background, flanked by trees that display early signs of changing seasons.

Townhouse in Hancock

4.92 out of 5 average rating, 115 reviews

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

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Top Guest favourite

A modern kitchen features a central island with bar stools, stainless steel appliances, and white cabinetry. Natural light floods the space through a skylight and large windows, highlighting the open layout. A dining area with dark chairs sits adjacent to the kitchen.

Apartment in Charlemont

5.0 out of 5 average rating, 201 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

Our happy place is a 5 minute walk to Berkshire East/Thunder Mountain . An 8 minute walk to the Deerfield River for guided fishing tours with Hilltown Anglers, kayaks, ,whitewater rafting. 10 minute walk to town and shuttle for tubing. A 5 minute drive to local wedding venues. We provide a full kitchen with all cooking essentials, a private picnic area with charcoal grill (charcoal provided). We reside at the single family home on property and we’re excited to share our Suite 23 !

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Top Guest favourite

The living room features a high, vaulted ceiling with large, triangular windows allowing ample natural light. A brick fireplace serves as a focal point, surrounded by a wooden mantel and decorative plants. A dining table sits nearby, and hardwood flooring is complemented by colorful area rugs.

Farm stay in Ashfield

5.0 out of 5 average rating, 153 reviews

Sunny Chalet Nestled in the Woods of Ashfield

Relax in a quiet sunny chalet located on land with established herbal gardens, offering privacy, space, and a comfortable base for families and small groups visiting Ashfield and the surrounding hills. This pet-friendly three-bedroom home is designed for guests who want a peaceful, rural stay with the reassurance of an attentive host nearby. Whether you’re visiting family, exploring the area, or enjoying time away from the city, the chalet offers room to unwind in a calm setting.

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Top Guest favourite

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

4.9 out of 5 average rating, 239 reviews

Hollywood Bungalow in the Berkshires #C0191633410

Cool Cozy Rustic Country Bungalow with 7.1 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, 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.

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Top Guest favourite

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, 178 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.

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Guest favourite

A modern cabin is nestled among lush greenery, featuring a wooden exterior and a wrap-around porch. Large windows provide views of the surrounding trees, while the gentle slope of the land leads to a grassy area in the foreground.

Guesthouse in Tivoli

4.9 out of 5 average rating, 210 reviews

Tivoli Star Gazing Cabin

Down a long driveway, set amongst 100 year old trees and meadows, the cabin offers time in the quiet country though only minutes to the lively village of Tivoli. With a wrap around porch for morning coffee, fire fly viewing or star gazing. It has a soaking tub, with a hand held shower. The cabin is part of our family compound of a main house and a small garden hut. Each property has an independent outdoor space for relaxing and privacy.

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