Ski-in/Ski-out vacation rentals in Hancock

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Top-rated ski-in/ski-out rentals in Hancock

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

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Guest favorite

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

4.93 out of 5 average rating, 251 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

Home in Wilmington

4.88 out of 5 average rating, 105 reviews

MtSnow * HotTub * Pool * Air Hockey * 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!

Guest favorite

The interior of the renovated studio cabin is seen from the kitchenette area. A bed, adorned with a patterned coverlet, is framed by a folding screen featuring floral and landscape designs. Artwork hangs on the walls, adding character to the warm space.

Guesthouse in Becket

4.93 out of 5 average rating, 272 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

A detailed map of Jiminy Peak reveals various landmarks and facilities, including lodging, dining, and attractions. Clearly marked trails and lifts illustrate the layout of the area, surrounded by a snowy landscape, providing an overview of the mountain experience.

Condo in Hancock

4.85 out of 5 average rating, 151 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

Home in Hancock

4.92 out of 5 average rating, 25 reviews

Summertime 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

The image depicts a charming blue house surrounded by a serene winter landscape. Snow-covered ski slopes rise in the background, with ski lifts visible along the mountainside. Leafless trees frame the scene, creating a peaceful atmosphere in a snowy setting.

Apartment in Hancock

5 out of 5 average rating, 10 reviews

Artsy loft near Williams 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 favorite

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

4.89 out of 5 average rating, 217 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 favorite

A spacious common area features a large stone fireplace as the focal point. Comfortable seating is arranged around wooden tables, with soft lamps providing light. Large windows allow natural light to fill the space, enhancing the inviting ambiance.

Vacation home in Hancock

4.96 out of 5 average rating, 24 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 favorite

A two-story home is shown with a sloped roof covered in snow. The entrance features a white door framed by large windows and a porch with wooden steps. Snow-covered shrubs line the pathway, providing a cozy winter touch.

Home in Otis

4.92 out of 5 average rating, 153 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

A snowy scene captures skiers preparing for the slopes outside multiple building complexes. Skis are propped against racks amidst the winter setting, while guests are seen gathered, adjusting gear and enjoying the snow-covered landscape.

Apartment in Hancock

4.97 out of 5 average rating, 37 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

A light-filled living area features a white couch adorned with striped cushions. A wooden coffee table sits atop a textured rug, while a small potted plant and candles are arranged on it. Large glass doors lead to an outdoor view with vibrant autumn foliage.

Home in Germantown

4.97 out of 5 average rating, 326 reviews

Fantastic Cottage/Insane 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 premium appliances. Total Privacy High ceilings, hand plastered walls, antique doors. Glass French doors open to a 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!

Guest favorite

A cozy nook features a broad window surrounded by lush greenery, allowing natural light to fill the space. A daybed with neutral linens and decorative pillows complements a simple wooden table adorned with books and a small vase of wildflowers.

Guesthouse in Tivoli

4.91 out of 5 average rating, 169 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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What guests are saying

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4

4.92 out of 5 average rating, 13 reviews1 month ago

The woodland suite was perfect for our weekend stay! Howard was responsive and accommodating when my plans had changed and was able to update my reservation as needed. The suite looked exactly like the pictures, and there were ample instructions on navigating the area (both for check-in and getting around the resort). The appliances were a mix of vintage for charm and modern for functionality and convenience. There was never a lack of amenities/toiletries either. The only downside, at no fault of the host, is if you happen to have noisy neighbors you'll unfortunately hear everything they do. The building itself seemed to have very thin walls, and paired with ski boots walking around it could get loud. The location though is still great for a ski-in/ski-out proximity

Apartment in Hancock

What guests are saying

Berkshire family getaway at Jiminy Peak!

4.92 out of 5 average rating, 91 reviews2 months ago

This place was fantastic. We were not sure what to expect having only been to this area many years ago, and were pleasantly surprised. Ron's place was amazing for our family of 5. The location was perfect and allowed our older boys to run back and forth to the house while we were at the mountain when they needed a break. We would definitely rent this place again when we return to Jiminy Peak. Thanks for a great weekend getaway!

Townhouse in Hancock

What guests are saying

StrautmanHaus: All-Season Chalet at Berkshire East

4.99 out of 5 average rating, 71 reviews2 months ago

Great stay slopeside at Berkshire East. We had a wonderful week and the house was perfect. We had some trouble with the weather (and power) that was out of host's hands but they went above and beyond to stay in touch and help get through it. Great spot for family skiing, or group trip mountain biking, rafting, etc. Thanks!

Chalet in Charlemont

What guests are saying

Mountainside Condo @ Jiminy Peak in the Berkshires

5 out of 5 average rating, 43 reviews1 week ago

Everything about our stay was great. The condo itself was very comfortable and had everything we would expect to need (and more). It was very clean, and an all around great setup. We had 4 people stay here while attending a work conference. It was extremely comfortable for that many people; both privately and socially. We liked it so much everyone in our group was asking if we could book the same condo for next year's conference. Also, we had another group of employees attending the conference who stayed in a different condo at another area of the resort. When they stopped by one evening to say hi, they asked if I could book their condo next year since our place was so nice. Two people in our group needed to be there earlier than the other two. The fact they were ready for us to check in a few hours early, and ok with us doing so, was a big help and greatly appreciated. I would absolutely recommend Gina and David's condo for anyone looking to stay at Jiminy Peak.

Townhouse in Hancock

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