It does not feel right not to include Massachusetts as a destination to explore and enjoy when you are thinking of vacationing in the United States. If you are fond of skiing, you will love Massachusetts. The state offers top-notch ski resorts, such as Jiminy Peak Mountain Resort, Nashoba Valley Ski Area, and Butternut Ski Area and Tubing Center. Other than skiing, you can admire a collection of contemporary art, drawings, and musical instruments from around the world at Museum of Fine Arts, Boston. You can also spend some time at New England Aquarium, which features more than 2,000 aquatic animals. For a place to stay in during your trip, read on to know about the top ski-in ski-out accommodations in Massachusetts, USA.
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 August 30, 2025.
1. Swiss chalet with a spacious deck (from USD 264)
This Swiss chalet is surrounded by a forest. If you want to reconnect with nature and escape from the bustling city, then you will love staying here. You can enjoy cross-country skiing right on the property when the snow is thick. High-speed internet and television are amenities available so that you can stay entertained. In summer or spring, you can relish your favorite cocktails on the deck, which overlooks the forest.
Peru, Massachusetts, United States
11.35 km (7.1 mi) from Wahconah Falls State Park
Top guest reviews
Host:
the owner was easy to communicate with and prompt to respondLocation:
very peaceful property with no close neighborsi highly recommend laura's place as a wonderful way to get away for a whileCleanliness:
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 cookingRead more reviewsAmenities & 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 was
2. Spacious house with an indoor fireplace (from USD 750)
This spacious house can accommodate a group of 12 travelers and features 4 bedrooms. Jiminy Peak Mountain Resort is just a short walk away. If you prefer to stay home, you can entertain yourself by watching your favorite movies on the Smart television. The place also has a jetted tub and a rain shower. You can stay warm by the indoor fireplace while sipping wine on a chilly evening. Other amenities include a fully equipped kitchen, a ski storage room, and Wi-Fi access.
Hancock, Massachusetts, United States
15.8 km (9.9 mi) from Wahconah Falls State ParkAccommodates: 12
Top guest reviews
Host:
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 hadLocation:
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 againCleanliness:
super clean and comfortableRead more reviewsAmenities & 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 comfortable
3. Create wonderful memories in Massachusetts
Massachusetts is an incredible place where you can engage in a lot of activities, such as skiing, fishing, and boating. You will have wonderful memories with your family or friends when you visit Massachusetts. You can refer to this list when you plan your skiing trip.
4. Bright cabin with a reading room (from USD 274)
You will have a relaxing stay at this bright cabin, which is surrounded by a forest of pine, maple, and birch trees. You can have a memorable riverside cross-country skiing experience here. The place features two bedrooms and one bathroom. It is designed to offer comfort for four people. Other amenities include a reading room, a back deck, and a large wood stove.
Chesterfield, Massachusetts, United States
27.23 km (17.0 mi) from Wahconah Falls State Park
Top guest reviews
Host:
thank you to robbie who was a gracious hostthanks to our hosts for a lovely staythe owners were very communicative and we had everything we needed for a great long weekendLocation:
location is remote but surrounded by beautiful naturesuper private great location lovely place to unwindinside and out just a wonderful place to spend timeCleanliness:
the house is modern clean quiet and spaciousthe house is cozy clean and brightvery clean and well maintained and robbie was a pleasure to work withthe property is beautifully renovated and was perfectly cleaned and prepped for our staythe cabin was impeccably clean and we just loved being a bit secluded and away from the normsRead more reviewsAmenities & Room:
beautiful home cozy fires and wonderful walks in the woodsthe glow room is delightful to experiencewe hope to be able to visit beautiful the glow room again soon
5. Elegant sanctuary with a lush garden
You will have an enjoyable stay at this elegant house, which is good for up to 14 people and is located right at the base of Mount Greylock. Ski slopes are just minutes away. It has seven bedrooms and three bathrooms. You can take a leisure walk around the lush garden after waking up in the morning. Then you can prepare your breakfast in the fully equipped kitchen. To end your day, you can share a bottle of wine with loved ones on the balcony.
Adams, Massachusetts, United States
15.18 km (9.5 mi) from Wahconah Falls State Park
Top guest reviews
Host:
property managers are very helpfuljill is a wonderful property manager and super responsivejill was very responsivethe property manager jill was exceptionally helpfuljill was a great property manager she was extremely helpfulLocation:
it is a gorgeous house in a beautiful location in the berkshiresgreat donut shop a short walk from the houseprivate quiet short driving distance to berkshire attractionsRead more reviewsCleanliness:
place was very clean with large well equipped kitchenit is super clean and the most charming house everbeautiful house very clean lots of space for everyoneit is immaculate well stocked and a beautiful house
Cozy apartment with heated pools
This cozy apartment, which is surrounded by mountains, boasts express lifts that can take you to Jiminy Peak Mountain Resort for your skiing adventure. It features two bedrooms and two bathrooms and promises a pleasant and comfortable stay for up to eight people. After a day of skiing, you can unwind in one of the hot tubs. The place also has indoor and outdoor heated pools where you can relax. There is a ski school for both children and adults in case you want to take some lessons.
16.36 km (10.2 mi) from Wahconah Falls State ParkSuperhost
Accommodates: 8
Top guest reviews
Host:
doug was a great hostthe staff are super friendly and helpfuldoug was super responsive and answered any questions immediatelythis was my first booking through airbnb and doug was so helpfulLocation:
the location was right on the mountain and was ski-on/ski-/off which was hugewe loved our stay perfect accommodations for a family of four and the location can't be beatclean great location perfect for our familyRead more reviewsCleanliness:
very clean and well equippedclean comfortable and welcomingadditionally the apartment was sparkling cleanincredibly clean and comfortable you can’t beat the location for skiing in/out
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