Ski-in/Ski-out holiday 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.

0 of 0 items showing

1 of 3 pages

Guest favourite

Condo in Hancock

4.95 out of 5 average rating, 59 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 favourite

Place to stay in North Adams

4.93 out of 5 average rating, 254 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 favourite

Home in Hancock

4.92 out of 5 average rating, 13 reviews

Comfortable Berkshires retreat on mtn resort, SISO

Once a retreat for an NYC real estate family, this grand yet comfortable place in Jiminy Peak has retained the feel of a chalet: perfect after a ski/hike/bike through the beautiful mountains around it. 4 bdrs allow your group to space out, and a great room with 20 foot high ceilings extends through the dining area. Convenient to many Berkshires spots (Tanglewood, museums, etc.), a 2nd living room, fireplace, jacuzzi, and access to slopes, hot tubs, heated pool & gym complete the perfect getaway.

Guest favourite

Guesthouse in Becket

4.93 out of 5 average rating, 274 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.

Top Guest favourite

Townhouse in Hancock

5 out of 5 average rating, 21 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!

Guest favourite

Apartment in Hancock

5 out of 5 average rating, 11 reviews

Artsy loft near MassMoCA with pool and hot tubs

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!

Guest favourite

Home in Williamstown

4.89 out of 5 average rating, 220 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 favourite

Holiday home in Hancock

4.96 out of 5 average rating, 25 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 favourite

Home in Otis

4.92 out of 5 average rating, 155 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 favourite

Apartment in Hancock

4.95 out of 5 average rating, 40 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 favourite

Home in Hancock

4.93 out of 5 average rating, 27 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 favourite

Condo in Hancock

4.91 out of 5 average rating, 69 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.