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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Guest favorite

Condo in Hancock

4.98 out of 5 average rating, 42 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Jiminy's GEM is everything you're looking for! The location is absolutely prime- steps from the highspeed 6pk lift with your balcony overlooking the beautiful mountain & apres fire pit. Enjoy 3 bdrms/3 full baths with enough beds to accommodate numerous families, sleeping a total of 10 people. Take advantage of a heated pool, hottub & gym when you're not enjoying the mountain. Summer and Leaf Peeping season are equally as entertaining and enjoyable. Let us make your trip better than imagined!

Guest favorite

Place to stay in North Adams

4.93 out of 5 average rating, 241 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, 267 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.

Guest favorite

Townhouse in Hancock

5 out of 5 average rating, 39 reviews

Jiminy Peak Mountainside Getaway in the Berkshires

This beautiful 3 bedroom, 3 full bath condo nestled in a quiet cul-de-sac is a short hop to the bunny ski lift! Newly renovated in Jan 2022, you will enjoy all new kitchen cabinets, appliances, countertops, flooring, vanities, toilets, & furniture. 2 living rooms, 2 TVs & extra amenities to make you feel at home. 2 parking spots, a ski locker & access to Jiminy's resort facilities. Relax on the deck or by the fireplace with Netflix, Prime, etc. This is THE PLACE to come back to year round!

Guest favorite

Condo in Hancock

4.84 out of 5 average rating, 139 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.

Superhost

Home in Hancock

4.89 out of 5 average rating, 19 reviews

Autumn at Left Bank Lodge

Welcome to the Berkshires and all that Jiminy Peak has to offer. This spacious townhome has all that you need for the perfect getaway, Winter, Spring, Summer and Fall. Bring the whole family and all the friends because there is more than enough room for everyone. Enjoy 3 floor living with 4 bedrooms, 3 full baths, fully equipped kitchen, 2 living rooms with fireplace and brand new trex deck with views for days. Skip the hassle of parking and take advantage of skiing right out your door!

Guest favorite

Vacation home in Hancock

4.94 out of 5 average rating, 16 reviews

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 favorite

Bungalow in Williamstown

4.88 out of 5 average rating, 207 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

Home in Otis

4.92 out of 5 average rating, 144 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.

Guest favorite

Rental unit in Hancock

4.96 out of 5 average rating, 27 reviews

Ski-InSki-Out Loft Lift&MT.Views

This ski-in, ski-out loft is located right at the base of the mountain in the Thatcher Lodge in the heart of the village at Jiminy Peak. Unmatched access to all of Jiminy Peak’s year-round activities. Skiing, mountain biking, hiking, tennis, swimming, fall foliage leaf peeping, shops, restaurants and the Mountain Adventure Park including the famous Mountain Coaster, Alpine Super Slide, Euro Bungy Trampoline, Soaring Eagle, Giant Swing, and climbing wall.

Guest favorite

Condo in Hancock

4.94 out of 5 average rating, 17 reviews

Large one bedroom, two full bath, full kitchen

Located in the heart of Hancock's premier ski-resort, Jiminy Peak this lovely appointed self contained apartment is ski on, ski off the 45 runs of the mountain. Perfect for a cozy Fall getaway to leaf peep all of the beautiful Berkshires. Close to Williamstown, North Adams, Lee, Lenox, Pittsfield and more. This is a year round spot with loads of activities. Pool, jacuzzi, exercise room and two restaurants are on site.

Guest favorite

Condo in Hancock

4.91 out of 5 average rating, 54 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.