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A Magic Spot: Booking year round.

Springtime at The Magic Spot! It's beautiful. In the woods, with birds and tulips (1200), lilacs and lots of rare lilies. Perfect for families. Art and books in every room. Excellent kitchen. A perfect vacation house. Hiking/birding/guided mushrooming. Nearby State Park for swimming. Near Tanglewood, Mass Moca, Clark Art Inst. IMPORTANT: Weekday BASE PRICE $200 for 2 bedrooms. Additional bedrooms $50 per room . Summer weekends $300/entire house. Discounts available. We say: "Welcome Home!"

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!

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

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.

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

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!

Hollywood Bungalow in the Berkshires #C0191633410

Cool Cozy Rustic Country Bungalow with 7.1 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, 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.

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.

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.

Cozy Cabin in the Berkshire Resort

Cozy Cabin at Jiminy Peak – Perfect for Couples, Friends & Families Escape to the heart of the Berkshires at our charming single-level cabin nestled within the Jiminy Peak Ski Resort. Whether it’s a romantic retreat, a fun trip with friends, or a family vacation, our home is the perfect base to explore everything the region has to offer—from outdoor adventures, hiking, and lake swimming to mountain rides and world-class arts, music, and cultural events.

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.

Berkshire Charm w/ Panoramic views

This is a new beautiful and tastefully renovated building high on October Mountain that offers panoramic views and amazing sunsets over the Berkshires. This intimate space has walking and cross-country ski trails, fire pit, gardens, decks, streams and more. While having a remote and rural feel you are located in the heart of Berkshire culture only minutes form Lenox, Lee and Great Barrington MA.