Ski-in/out vacation rentals in Massachusetts

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

Top-rated ski-in/out rentals in Massachusetts

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Place to stay in North Adams

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 favourite

Home in Westminster

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

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

Guest favourite

Chalet in Charlemont

StrautmanHaus: All-Season Chalet at Berkshire East

Welcome to StrautmanHaus, a Bavarian style A-Frame home, nestled at the base of Berkshire East Mountain Resort. This charming chalet is newly renovated, with 4 beds/2 baths/4 decks and stunning views that sleeps 10! Surrounded by mature growth pine trees, the property offers a perfect combination of privacy and ski-on/off access to Berkshire East. In the summer & fall, you have on-site access to the resort’s mountain biking/white water rafting/zip line/mountain coaster & aerial adventure park.

Guest favourite

Rental unit in South Hadley

River front property

Unique 2 bedroom guest house on the Connecticut River in South Hadley, Sleeps 8 1 bathroom Covered parking Dock available Kayaking Boat rental available Paddle bikes and boards Views Fire pit Tour boat next door at Brunelle’s Marina. Patio Ice machine Boathouse restaurant Village commons 1 mile away McCrays farm 1 mile away Ledges golf course 2 miles away Malls etc. 15 min MGM casino 15 min Basketball hall of fame 15 min Airport 45 min Amtrak 10 min Mt sugarloaf 20min. Hiking trails

Guest favourite

Guesthouse in Becket

Country Cabin

Lovely private country setting. 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 the request.) The space is for 2 adults but I allow for flexibility, 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.

Guest favourite

Condo in Hancock

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 favourite

Condo in Hancock

Upscale 2 bed/2bath Condo at a Mountain Resort!

A beautiful newly renovated two bedroom condo with A/C at Jiminy Peak Mountain Resort. This natural light filled 1130 sq. ft. condo can accommodate up to 4 people with 2 bedrooms. Two full baths, a washer and dryer as well as a full kitchen will make this your home away from home. This convenient location is just a short distance from area lakes, hiking trails, restaurants, shopping and cultural venues. Take advantage of Jiminys' pools when you're not enjoying the Mountain Adventure Park!

Guest favourite

Home in Ashfield

Sunny Chalet Nestled in the Woods of Ashfield

Need some time to recharge and replenish? Whether a group of friends, family or a couples getaway - this property will suit all your needs. Access to hiking right out the door and loads of recreational activities such as skiing, swimming, biking. Our high speed WiFi and TV support streaming. Curl up on the couch and bask in the sunlight through the windows. Read a book by the fire. Gaze up at the stars and moon from the deck. Share a meal. A perfect spot for a retreat or family gathering.

Guest favourite

Vacation home in Hancock

Ski in/Ski Out - Building 1 Condo at Jiminy Peak

*NEW to AirBnB* 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 favourite

Guesthouse in Brockton

Majestic home in Brockton

Welcome to our house, we offer a bright and cozy guest house. Ideal for 4 or 5 people looking for the perfect space. Our modern guesthouse is in a beautiful and quiet neighborhood designed to take into consideration every detail you need to enjoy your stay in Brockton. supermarket, & pharmacies. Within 3 miles you have an MBTA commuter station and a Westgate shopping center. This place has been professionally cleaned, and sanitized after each use. Feel free to text me anytime.

Guest favourite

Bungalow in Williamstown

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 favourite

Home in Otis

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.