Berkshires, situated in the northeastern United States, is a mountainous region blessed with stunning natural beauty. Some of the places you can visit here include Pleasant Valley Wildlife Sanctuary, Natural Bridge State Park, Berkshires Botanical Garden, Bish Bash Falls and Monument Mountain. Berkshires has museums of famous authors and artists such as Herman Melville, Edith Wharton and Norman Rockwell who chose to stay here because of the peaceful atmosphere. In summer, you can swim in Green River, hike in Kennedy Park and kayak in Goose Pond. Berkshires has many accommodations close to mountain resorts where you may go for skiing, tubing, snowboarding, ice boating and snow kiting. Keep reading to learn more about the top ski-in ski-out accommodations in Berkshires, Massachusetts.
We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to ski slopes and equipment. The image galleries get refreshed with the latest updates regularly. They were last updated on April 14, 2024.
1. Jiminy Peak Mountain Resort, Hancock (from USD 145)
You may be glad to know that Jiminy Peak Mountain Resort gets 100% of its power from renewable energy sources. Rent skis, snowboards, helmets, ski poles and boots at the resort. You may purchase half-day, full-day or multi-day ski-lift passes depending on the duration of your stay.
The instructors at the resort can offer group or individual skiing and snowboarding lessons tailored to the age and experience of the guests. Additionally, warm up in the heated whirlpools when you return.
Jiminy Peak Mountain Resort
Address: 37 Corey Rd
376 meters (0.3 ft) from Jiminy Peak Mountain Resort
Top guest reviews
Cleanliness:
we enjoyed it there and the one bedroom we had was clean and niceplace was clean with friendly staffRead more reviewsLocation:
next time i hope i can stay close to the slopesEarn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.
2. Pet-friendly cabin with a garden, Hancock (from USD 289)
This cabin is a three-minute walk from the Jiminy Peak ski resort so it is convenient for skiing and snowboarding. You may buy groceries from the nearby convenience store and cook meals on the charcoal grill, cooker or oven.
On days with pleasant weather, you can play with your pet in the shared garden. You may pass the time in the hot tub, outdoor pool or beside the fireplace on cold days. The cabin has board games and DVDs for entertainment.
Top guest reviews
Amenities & Room:
our two boys shared the trundle room and were cozyCleanliness:
the cabin was absolutely great everything was so clean and it was quite spaciouseverything was clean and it was easy to enjoy the pool and the outdoor adventure parkfantastic family time away with serene surroundings and a cozy spotless cabinHost:
kim was such a wonderful hostkim was the textbook definition of a great host: helpful responsive kindkim is a fantastic host super responsive flexible and helpfulkim is awesome kind responsive and communicates instructions very clearRead more reviewsLocation:
her home was in a fabulous location- walking distance to slopeskim was great- place was walkable to ski liftsgreat place to stay clean and convenient location with a lot of things to do nearby
Superhost
3. Comfortable two-bedroom condo with bright interiors, Hancock (from USD 325)
The condominium is located at Crane Lodge in Jiminy Peak close to the Berkshire Expressway lift. If you crave a change from skiing, hiking or mountain biking, you may work out in the nearby gym. You can also use the free Wi-Fi to post photos and videos on social media.
After making smoothies in the blender, you may sip them while watching your favourite shows on the television. In case you feel like taking a nap in the afternoon, you can use the room-darkening shades in the bedroom.
Top guest reviews
Cleanliness:
the place was extremely clean well decorated and comfortablewhat a special spot the condo was spotless and really niceHost:
amazing place amazing hosts :)she was incredibly kind thoughtful and responsivewe highly recommend this wonderful condo and the great hostsRead more reviewsLocation:
amazing location pristine apartment everything was wonderfulthe airbnb is extremely well decorated and stocked and is the perfect location for skiingwhat a great place to stay
4. Middle Way Farm, Lee (from USD 199)
Middle Way Farm is situated on the top of October Mountain so you can enjoy wonderful views of the forest and fields. You may walk through the orchards, hike beside the streams and go skiing on the cross-country trails.
If you need to do laundry, the house has a washer and dryer. You may also bake cakes in the oven and enjoy them with a cup of coffee on the balcony while watching beautiful sunsets.
Top guest reviews
Amenities & Room:
there is no tv but the wifi works greatthe view is breathtaking and the loft is incredibly comfortable and relaxingbasic cooking utensils/pots & pans comfortable bed and a couple cozy chairs to sit in toothe view from the windows and bathroom is stunningamazing views of the mountains and cozy atmosphere makes you feel so relaxedCleanliness:
very clean and open spacethe cabin was clean and very comfortablethe apartment is very comfortable and spotlessly cleanthe space is clean and open with a yogi vibethe loft was clean and so relaxing highly recommendedHost:
host was easy to contacthost was friendly and helpfulgreat host and a great placejohn was super helpful and quick to respond with recommendations and directionsthe owner improved everything myself and others had left feedback aboutRead more reviewsLocation:
wow what a location to staythe location was silent and relaxingthe location is wonderful; near great barrington and great hiking trailsthe location was very nice and relaxinggreat location beautiful and peaceful setting
5. Spacious house with ski storage, Hancock (from USD 850)
This four-bedroom house is a few minutes away from the Grouse Run ski trail. You may use the snowshoes available here and keep the skis in the storage room when you are not using them. If you are arriving by car, there is parking available in front of the house.
Your children can enjoy the toys or board games while you read the books available here. You may also do yoga while listening to your favourite tunes on the Sonos sound system.
Top guest reviews
Amenities & Room:
very comfortable and had all the amenities you could needthe welcome goodie baskets in the kitchen and bathrooms rivaled a 5-star hotelthe beds were luxuriously comfortableCleanliness:
super clean and comfortableHost:
the owner was also very helpful and responsivevery quick ot reply and extremely helpfulhost is super considerate and warm heartedgreat house and great host howard always responded quickly and had great local suggestionsi really appreciated the communication from the host for any questions we hadRead more reviewsLocation:
this is a fantastic place in a great locationthe walk to the trails is relatively short and connects to an easy trailthe house is right on the mountain and was easily accessible to the lifts with a short walka couple minutes to a semi-private pool fun amusement parks and many local “must do” spotswe really loved the place and hope to return again
6. Cosy condo with a dedicated workspace, Hancock (from USD 263)
When you stay at this mountainside condo, you can walk with your skiing equipment to the Bunny Hill ski lift or store the gear locker at JJ’s Lodge. If you prefer to exercise indoors, you may work out using the weights, stationary bike or treadmill available at the gym.
The condo has a dedicated workspace with Wi-Fi which you can use for video conferences. You can also play video games using Nintendo Switch, listen to music on Echo Dot and watch television.
Top guest reviews
Amenities & Room:
the couch and bed were so comfortablethe condo was extraordinarily well-stocked and had a fantastic organized and clean kitchenwe enjoyed the pools and the adventure park and the food options at the various restaurants on siteCleanliness:
the condo was clean and nicely decoratedthe condo was spacious and clean and comfortablethe space was very clean and comfortable and there was always great communicationthe place is exactly is described- very spacious clean and so invitingthe townhouse itself is well maintained clean quiet and very comfortable to stay atHost:
gina & david were very attentive and responsive hostsgina and david were fantastic hoststhe owners were very responsive and accommodatingowners were gracious & very responsivegina and dave are very responsive and any questions and requests made were immediately addressedRead more reviewsLocation:
super comfortable place and just a short walk to the mountainluckily we found gina and dave's place right next door to wyndhamwe enjoyed our stay the townhouse is in a fun location at jimny peakthree of us stayed at this location and were impressed with the attention/care of the guestsquiet and safe extremely well stocked
7. Three-bedroom condo with kitchen, Hancock (from USD 251)
The location of this condo is near JJ Lodge at Jiminy Peak Mountain Resort making it a good base for skiing and mountain biking. In case you feel cold, you may relax beside the electric fireplace or at the hot tub nearby. The kitchen has a toaster, stove, microwave and oven which you may use to prepare meals or quick snacks.
For refreshments, make tea using the kettle and sip it while enjoying the mountain view from the porch.
8. Wyndham Bentley Brook, Hancock (from USD 492)
Wyndham Bentley Brook is located close to a ski lift at Jiminy Peak Mountain Resort. You may store your skis in the locker downstairs. On stormy days, you can swim in the indoor pool and exercise on the treadmills or stationary bikes in the gym.
You may also play snooker or tennis with your companions and relax in the sauna or hot tub. In case your clothes get dirty, you can use the washing machine and dryer available at the resort.
Top guest reviews
Amenities & Room:
great room to accommodate two familiesthe whole family enjoyed the pool and hot tub after a day on the mountainCleanliness:
the condo was clean and attractiveplace was clean and neatthe one we were in was dated but cleanRead more reviewsLocation:
this is the ideal ski-in/ski-out location for jiminy peakeverything is pretty clean and the location is amazing
9. Secluded vintage house surrounded by a forest, Peru (from USD 235)
This charming house in Peru is beautifully adorned with wooden beams. You can go for walks in the forest which also has a stream. The house has three pairs of cross-country skis and is close to skiing trails.
Guests can stay occupied by playing board games, listening to music on CDs, playing the piano and reading books. Please note that cellphones generally do not work but you can make calls using the landline or Wi-Fi.
Top guest reviews
Amenities & Room:
we didn’t have cell phone reception but the wifi was strong enough for streaming and cell phone usethe beds and beddings were very comfortablehouse had all the needed amenities comfortable beds and a pleasant overall cozinessthere was plenty of room and good sleepong space for alli loved cooking in the kitchen and we couldn't get over how beautiful the night sky wasCleanliness:
clean place with beautiful windows/lightingthe house was very clean and decorated with nice little touches in every cornera well-designed house generously furnished and supplied sparkling clean comfortableevery thing was perfect and so very cleanthe house is very clean and has most everything you need for cookingHost:
the owner was easy to communicate with and prompt to respondRead more reviewsLocation:
very peaceful property with no close neighborsi highly recommend laura's place as a wonderful way to get away for a while
10. The Greylock Getaway, Adams (from USD 243)
This house is located at the base of Mount Greylock where you can go skiing and snowshoeing. You may also use the available bicycles to explore the neighbourhood. If you have kids, they can be occupied with toys, puzzles or board games while you prepare meals in the kitchen.
Moreover, you can relax by reading books or watching television. The owner allows pets if you pay extra.
Enjoy skiing in Berkshires
Berkshires has many accommodations which have skis, storage lockers or nearby shops from where you can rent equipment. In case you wish to take a break from skiing, you may visit nature parks or museums. Book one of the top ski-in ski-out accommodations on this list to enjoy your vacation in Berkshires, Massachusetts.
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