Holiday rentals in Jiminy Peak

4.94 out of 5 average rating, 416 reviews

Chalet in Otis

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

4.85 out of 5 average rating, 40 reviews

All-season Berkshires ski resort condo - Sitzmark

Stay at the Jiminy Peak mountain resort near renowned museums, music, dance and theater in the beautiful Berkshires. You'll be steps from swimming, hiking, aerial adventures and thrill rides. Meals are easy with two resort restaurants, a country store and a fully equipped kitchen. Spend your days at Tanglewood, Hancock Shaker Village, Mass MoCA and other nearby attractions. Then relax on the deck or in front of TVs in each room. Return for skiing in the winter with a fireplace for extra warmth.

4.98 out of 5 average rating, 44 reviews

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.

4.88 out of 5 average rating, 184 reviews

Flat in Petersburgh

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Space is 14 x 28 feet and includes living/dining/work space, bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed with pull out twin mattress. High def TV, wifi, private deck, kitchenette has mini fridge, microwave, toaster oven, hot kettle for tea and and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

4.89 out of 5 average rating, 188 reviews

Cottage in Williamstown

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 pull out couch.. Dog friendly for up to 2 dogs .More than one dog will have to be an additional fee of 50.00 each pet. My cottage sits on 13 privately owned acres. Partially fenced in.3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!

5 out of 5 average rating, 19 reviews

Townhouse in Hancock

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!

4.95 out of 5 average rating, 174 reviews

Home in Pittsfield

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

5 out of 5 average rating, 10 reviews

Flat in Hancock

Artsy loft near MassMoCA with pool and hot tubs

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!

4.98 out of 5 average rating, 692 reviews

Cottage in Shaftsbury

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 350 acre property.

4.96 out of 5 average rating, 24 reviews

Holiday home in Hancock

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.

4.94 out of 5 average rating, 32 reviews

Home in Hancock

Bougie B’s Mountainside Getaway

Escape to our updated 2-bedroom, 2-bath condo at Jiminy Peak! Perfectly situated for the ski season, you'll enjoy quick access to both the slopes and apres ski. After a day on the trails, unwind at nearby restaurants like Christianson's Tavern or Bluebird & Co, offering top notch local eats. Bougie B's features updated amenities and that perfect touch of class to make you feel special. Come experience the beauty of the mountains today—your perfect escape awaits!

4.91 out of 5 average rating, 23 reviews

Large one bedroom, two full bath, full kitchen

Located in the heart of Hancock's premier ski-resort, Jiminy Peak this lovely appointed self contained apartment is ski on, ski off the 45 runs of the mountain. Perfect for a cozy Fall getaway to leaf peep all of the beautiful Berkshires. Close to Williamstown, North Adams, Lee, Lenox, Pittsfield and more. This is a year round spot with loads of activities. Pool, jacuzzi, exercise room and two restaurants are on site.

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Other great holiday rentals in Jiminy Peak

Guest suite in Hancock

4.81 out of 5 average rating, 180 reviews

Cozy apartment near Jiminy Peak

KatieRating, 5 stars3 months ago

We loved staying with Naren! She was very accommodating and has a beautiful home:) Highly recommend and would love to return!

Home in Hancock

4.83 out of 5 average rating, 12 reviews

Beautiful 4 Bedroom Townhouse in the Berkshires

LindaRating, 5 stars3 months ago

This home was the perfect place for our family/friends gathering. Location was fantastic - just a short 1-2 min walk to the ski-in spot, making it incredibly convenient for hitting the slopes with little ones. The host was exceptionally informative and friendly, ensuring we had everything for a comfy stay. Kids had fun sledding between the houses and grownups loved the hot tub.

Home in Hancock

4.88 out of 5 average rating, 8 reviews

Snowdrop Lodge: Beautiful Condo at Jiminy Peak

BrianRating, 5 stars5 months ago

It was great to be on the property at Jiminy Peak walking distance to the lodge and mountain. Place was adorable. Perfect for our family of four. They had garbage bags, soap and all the necessities. Would definitely stay there again.

Campervan/Motorhome in East Nassau

5 out of 5 average rating, 30 reviews

The Hawk's Nest

RupamRating, 5 stars2 weeks ago

Great host and great location. Very peaceful and everything was provided to make the glamping experience a memorable one. Will return soon.

4.83 out of 5 average rating, 84 reviews

Cottage in Hancock

Berkshire Cottage Queen Bd-Jiminy Peak 3 mi

KellyRating, 5 stars5 days ago

Renee was always responsive when we messaged. The Airbnb was super clean and the bed was very comfortable. Check in was so easy! At the end all Renee asked of us is to take the trash out which was super easy. I would definitely recommend this place. It is an especially good location for people who are attending a wedding at Bloom Meadows which is about 2 minutes away.

4.97 out of 5 average rating, 31 reviews

Cabin in Cambridge

Pond View Cabin. Off-Grid, Rustic & Dog Friendly.

EmilyRating, 5 stars1 week ago

Highly recommend Brian’s off grid cabin! His directions were very helpful and made navigating the generator, camp shower, and other on-site details super easy to understand and execute. His property is beautiful and peaceful. We’re already looking at our calendars for another time to visit. Our dog, Stumpy, very much enjoyed the outdoor access and pond. He didn’t want to leave!

4.6 out of 5 average rating, 148 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

BenRating, 5 stars3 months ago

We had a great stay here. It was very close to the ski lifts, and the ski locker was directly across the hall. It made for a very enjoyable and easy skiing experience. Jiminy Peak is a great place to ski at with a variety of trails for all skill levels, and even though it was a school vacation week/weekend, the lift lines were never long. Margaret was very responsive to any questions we had and made the process easy. We loved it!