
Ski-in/Ski-out holiday rentals in Berkshire County
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Top-rated ski-in/out rentals in Berkshire County
Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

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

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2
Ski-in,ski-out! Unbeatable location for all seasons! Closest condo at JiminyPeak to the slopes and lifts. Located right at base of Mt. in JJ’sLodge in the heart of JiminyVillage. Mere steps to BerkshireExpress HighSpeed 6pack! Amazing pano views of the slopes surround. Designated pkg space in owner’s pkg lot. Unmatched access to all JP’s year-round activities. Skiing,MtBiking,hiking,tennis,swimming,fall foliage leaf peeping, shops,restaurants,MtAdventurePark w/ famous MtCoaster&AlpineSuperSlide.

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.

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!

1st Floor Mountain View Suite Ski On/Off At Jiminy
You want to pop out of bed, walk down hall, and be right on the mountain This 1BR 1 BA Ground Floor Unit Charming Mountain Decorated Suite right by the entrance features a king bed in the master bedroom, plus a fold out queen sofa bed in the living room. The kitchen comes complete with all your needs, incl Keurig, pots, pans, etc. The unit is equipped with board games , along with smart TVs that have all your favorite shows . The Inn amenities are yours including heated year round pool

Ski-in/Ski-Out on Jiminy Peak
Jiminy Peak Mountain Resort is the perfect Berkshire get away surrounded by cultural attractions and with skiing, mountain biking, snow shoeing, mountain coaster, ropes course and MORE right on property! For an easy convenient trip once you arrive you will not have get back into your car. Jiminy Peak has everything you need on property bar/restaurants, ski/ snowboard shop, general store, ski/snowboard and snowshoe equipment rentals, ski/snow lessons and school, day care, souvenir shop.

Artsy loft surrounded by fall foliage with hot tub
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!

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.

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.

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.

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. 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.
Popular amenities for Berkshire County ski-in/out rentals
Ski-in/out house rentals

A Magic Spot: Booking year round.

Knoll Rock House (3B/3B) - Best of the Berkshires

Beautiful 4 Bedroom Townhouse in the Berkshires

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Pe

Smiling Dog Meadow

Berkshire Lake-side Retreat

A simple kind of paradise

Cozy Ski Cabin in Berkshires Resort
Family-friendly, ski-in/out home rentals

Mountain View Jiminy Peak Ski On Off sleeps 4

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Catamount Lodging Ski In/Ski Out

Gorgeous Mountain View Suite Ski On/Off At Jiminy

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4
Ski-in/out apartment rentals

Condo Resort at Jiminy Peak Ski Mountain's Base

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

Wyndham Bentley Brook

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Unique - Country suite @ Jiminy Peak

Large one bedroom, two full bath, full kitchen

Jiminy Peak Country Inn 1 Bedroom Suite
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- Ski-in/ski-out rentals Massachusetts
- Ski-in/ski-out rentals United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Kent Falls State Park
- Zoom Flume
- Catamount Mountain Ski Resort
- Bushnell Park
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Taconic State Park
- Mount Sugarloaf State Reservation
- Opus 40
- Mohawk Mountain Ski Area
- Beartown State Forest
- Mount Tom State Reservation
- Mount Snow Ski Resort
- Bousquet Mountain Ski Area
- Hartford Golf Club
- Bright Nights at Forest Park
- Albany Center Gallery
- Talcott Mountain State Park