Ski-in/Ski-out holiday rentals in Jiminy Peak

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Top-rated ski-in/out rentals in Jiminy Peak

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Guest favourite

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 favourite

Home in Ashfield

5 out of 5 average rating, 114 reviews

Sunny Chalet Nestled in the Woods of Ashfield

Need some time to recharge surrounded by nature? Whether a group of friends, family or a wedding party - 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

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 favourite

Guest house 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 favourite

Apartment 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.

Superhost

Chalet in Dover

4.65 out of 5 average rating, 31 reviews

Mount Snow Chalet w/ Ski-Home Trail & Indoor Sauna

Welcome to your Mount Snow Ski House! (FYI: no hidden fees, low cleaning fee, no hassle on exit) Spacious, recently renovated 4 bedroom chalet w/ 2 living rooms and full sauna. Our neighborhood's private ski-off trail drops off about a minute walk from our front door, and the shuttle to Mt Snow base picks up even closer than that. Warm up by the fire in our large central living area after a day on the slopes, or enjoy neighborhood amenities in the shared clubhouse w/ ping pong table.

Superhost

Home in Dover

4.91 out of 5 average rating, 82 reviews

FULLY renovated 1 bed/1 bath ski in-out condo!

Can't get closer to on the slopes than skiing to your door! Walk 100 ft. to the lift, ski locker at entrance. Nothing untouched, FULLY RENOVATED AND STOCKED 1 bd/1 ba unit w QN bed and QN sleeper sofa. Large closet with sheets, pillows, blankets, towels. Bath w/ soaking tub! Full size washer and dryer. Kitchen stocked with appliances, coffee maker, pots, pans, spices, paper products everything you need to cook! Wood burning fireplace, LARGE TV. All new furniture. Office and dining room.

Guest favourite

Home in Dover

5 out of 5 average rating, 13 reviews

Hot tub | Shuttle | Ski back home!

Quintessential Vermont! Located at the end of a cul-de-sac and adjacent to the National Forest, this cozy-yet-spacious home offers a peaceful, private escape. Accommodations include a private hot tub, free MOOver ski shuttle on weekends/holidays, and a ski trail home weather permitting. Guests have access to clubhouse with fitness room and game room. For summer rentals, Memorial Day through Labor Day, enjoy the community's heated, outdoor pool, pickle ball courts and hiking trails!

Guest favourite

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 favourite

Holiday 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 favourite

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 favourite

Flat 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.