Ski-in/Ski-out vacation 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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Guest favorite

Cottage in Hollis

4.87 out of 5 average rating, 231 reviews

Lakefront Nature Getaway - Wood fired Cedar Sauna

Rustic getaway directly on lakefront - 60 feet from the water with private sauna. Private entrance, Pellet stove, 50" & 40" TV, Roku in each room, Soundbar, fast Internet w/ WiFi. Private cabin/apt is for nature lovers, hikers, artists, writers, snowmobilers, xc-skiers, fatbikers, fisherman & more. Bald Eagles are a daily sight. The BEST AirBnB in Hollis- the most amenities. Summer and Winter activities ** IMPORTANT: No Tobacco - all guests must be listed in reservation, dogs by request only

Guest favorite

Place to stay in North Adams

4.93 out of 5 average rating, 247 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

Guest favorite

Guesthouse in Becket

4.93 out of 5 average rating, 269 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. I only accept advance reservations of 2 nights or more. (You may reserve a single night booking within 5 days of request.) 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.

Superhost

Home in Westminster

4.81 out of 5 average rating, 122 reviews

Lakefront; view of ski mtn, firepit, dock, kayaks!

A charming lake house with a magnificent view of a ski mountain — Wachusett Ski Resort (voted #1 in MA). Newly-renovated, 650 square foot cabin with a wall unit AC, fire pit, grill, smart TVs, kayaks, paddle board, and all the amenities you’ll need. (FYI: We also own another lakefront Airbnb right down the street that accommodates 10 guests. Ask for link.) *A brand new retaining wall and dock will be installed May 2024. This will extend and even out the lawn for nights around the firepit!

Guest favorite

Condo in Hancock

4.85 out of 5 average rating, 142 reviews

Cozy Condo @ Jiminy Peak

Nestled in the majestic Berkshire mountains, this Cozy Condo is a home away from home! It features 2 bedrooms with closets & dresser space. The master bedroom connects to a full bathroom and has a TV for when it's time to unwind in the comfort of bed! The fully equipped kitchen/dining area opens into a spacious living room. It's the perfect place for evening gatherings with friends or a romantic night in front of the fireplace! Free access to 2 heated pools, hot tubs, sauna & fitness center.

Guest favorite

Rental unit in West Granby

4.9 out of 5 average rating, 130 reviews

Majestic Farmhouse Private & Peaceful Guest Apt.

Welcome to the Joab Griffin House. We are a beautiful historic farmhouse set on a private hill tucked away in the foothills of the Berkshires, surrounded by gorgeous farmland and hundreds of acres of land trust and game refuge trails, streams, and waterfalls within a five-minute walk from your door. Enjoy a private apartment in this lovely farmhouse. Here, you'll find cool summer breezes, cozy, warm, sun-filled days, and star-filled skies with the sounds of the brook outside your window.

Guest favorite

Home in Germantown

4.96 out of 5 average rating, 298 reviews

Modern Country Cottage, Views, Trails, Fireplace!

A Unique Modern Cottage with Stunning Views / A Spa like Bathroom/ A Charming Gas Fireplace/ Fully equipped Chef's kitchen/Soapstone countertops/New appliances. Total privacy, high ceilings, hand plastered walls, antique wood doors. Glass doors open onto private deck Enjoy big Catskill Mountain and seasonal Hudson River views. The large bath has a tiled glass door shower and a soaking tub. A Fieldstone fire pit overlooks the Catskills! For more photos at @martinasplaces at insta/gram

Guest favorite

Bungalow in Williamstown

4.89 out of 5 average rating, 211 reviews

Hollywood Bungalow in the Berkshires

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

Cabin in Prattsville

4.92 out of 5 average rating, 208 reviews

Little Red Cabin Near Windham & Hunter w/ Hot Tub

Nestled in the woods, our 3 bedroom cabin offers the perfect escape from the hustle and bustle of everyday life. The cozy interior features a warm, inviting atmosphere with all the amenities you need for a comfortable stay. The spacious living room is the perfect place to unwind after a long day of exploring the great outdoors, complete with a cozy fireplace and outdoor hot tub that offer stunning views of the surrounding landscape. Follow us on IG @thelittleredcabinny

Guest favorite

Guesthouse in Tivoli

4.93 out of 5 average rating, 153 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.

Superhost

Cabin in Woodford

4.84 out of 5 average rating, 362 reviews

400+ Airbnb Visits: Incredible Mountain Cabin

Our cabin is off the grid, NO running water (read this twice) or indoor bathroom, but it’s comfortable and has been enjoyed by 100’s of Airbnb travelers. There is electricity, but this cabin takes an adventurer in the winter months. Winter Stays take work! Don’t be surprised of shoveling and bringing in your gear! Our reviews speak for how great rental is for people, thank you for considering a stay at our cabin.

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 728 reviews

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.