Vacation rentals in Jiminy Peak

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Top-rated vacation rentals in Jiminy Peak

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Superhost

An outdoor deck is furnished with two brown adirondack chairs beneath a striped umbrella. Decorative pillows with floral designs add a colorful touch. A grill is positioned nearby, surrounded by lush greenery, enhancing the natural setting.

Condo in Hancock

4.85 out of 5 average rating, 39 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.

Top guest favorite

A Victorian house is framed by colorful autumn foliage, set within a spacious yard covered in fallen leaves. Long shadows stretch across the lawn, creating a serene atmosphere as sunlight filters through the trees, highlighting the inviting wraparound porch.

Apartment in North Adams

4.98 out of 5 average rating, 560 reviews

See MoCA from your mansion+Sauna!

This two-floor 4 bed apartment is tucked away on a hilltop oasis above Mass MoCA (3 mins by foot). It is fully private and occupies the second and third floors of the Small Mansion, a two family Victorian house (there are no shared spaces with the apartment downstairs). 5-10 mins drive to Williams, Clark. Whimsically restored (fast Wi-Fi & great water pressure). Most importantly, your stay’s proceeds allow us to host refugee/immigrant musicians pro bono year-round! @chasehillartistretreat

Guest favorite

A charming stone building is surrounded by lush greenery and colorful flowers, including pink and white blossoms. The sign, featuring 'Stone School Cottage,' is prominently displayed. Large windows indicate a bright interior. The setting offers a peaceful and inviting entrance to the accommodation.

Cottage in Lanesborough

4.93 out of 5 average rating, 241 reviews

Stone School Cottage

Romantic getaway or family vacation. Charming stone building served as a one-room schoolhouse from 1832 until 1950. Beautifully situated amidst horse farms on the scenic road to Mt Greylock, centrally located midway between Williamstown and Lenox. We host lots of writers and musicians who love the bright airy space, families that have fun in this big playhouse, and couples seeking a memorable and private retreat. PLEASE NOTE: this truly-unique building has an unusual layout, described below.

Top guest favorite

A cozy outdoor seating area is highlighted by a stone fire pit, with flames dancing above a bed of volcanic rocks. In the background, a high-definition TV displays a sports event. Barstools and a wooden structure suggest a welcoming spot to relax.

Apartment in Petersburgh

4.88 out of 5 average rating, 180 reviews

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.

Top guest favorite

An airy open-plan living space is highlighted by large windows allowing natural light. A sectional sofa is positioned near a modern fireplace, complemented by a wooden dining table set for six. Decorative rugs add warmth to the hardwood flooring, enhancing the welcoming atmosphere.

Townhouse in Hancock

5 out of 5 average rating, 17 reviews

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!

Top guest favorite

The image displays a private deck overlooking a lush green lawn bordered by trees. In the distance, vibrant fall foliage and rolling hills are visible under a clear blue sky, creating a serene natural backdrop.

Apartment in Canaan

4.99 out of 5 average rating, 158 reviews

Mountain View Getaway

Come relax & enjoy panoramic mountain and pond views. Marvel at the dramatic lighting effects on Mercer Mt from sunrise-sunset from your private deck or bright living room. Fully equipped kitchen, grill on the deck, short scenic drive to a wide variety of restaurants & endless cultural venues in the surrounding quaint villages of Berkshire County Mass and Columbia County NY. Near hiking trails, skiing, apple picking & farm stores. Queechy Lake swimming, NYS boat launch for car top boats.

Superhost

A small, vibrant pink shed is surrounded by greenery, featuring large windows that provide natural light. Nearby, a stone lantern and a decorative rock arrangement accentuate the outdoor space, while a small, colorful tree adds a touch of autumnal beauty.

Home in Dalton

4.88 out of 5 average rating, 138 reviews

The Yellow House

The Yellow House in the Berkshires is the perfect place for a getaway, just 2. 5 hours from NYC and 2 hours from Boston. This historic small town offers many activities including Jacob's Pillow, hiking trails, skiing, Mass MoCA, and The Clark Art Institute. It is close to Tanglewood in Lenox and the Norman Rockwell Museum in Stockbridge. Located steps away from The Stationery Factory, which houses a food market, gallery spaces, artisan shops, coffee shop, and the Shire Brewhouse & pub.

Top guest favorite

A serene outdoor seating area is framed by a large tree, with two wooden chairs positioned beside a round table. Sunlight filters through the leaves, casting dappled shadows on the lush green lawn that gently slopes in the background.

Guest suite in Williamstown

4.96 out of 5 average rating, 231 reviews

Berkshire Guest Suite

Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.

Guest favorite

A clear blue pool is surrounded by several lounge chairs and green umbrellas. Lush green hills rise in the background, with trees dotting the landscape. Buildings are visible along a winding path leading to the pool area, emphasizing the natural setting.

Apartment in Hancock

5 out of 5 average rating, 10 reviews

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!

Top guest favorite

Two friendly dogs are seated on a wooden deck. One dog is a small corgi with a charming pose, while the other is a larger, darker dog with upright ears. The deck space is tidy, suggesting a welcoming setting.

Farm stay in Pittsfield

5 out of 5 average rating, 202 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Guest favorite

Apartment in Hancock

4.97 out of 5 average rating, 38 reviews

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.

Guest favorite

A clear blue swimming pool is surrounded by a concrete deck, with lush greenery and tall trees visible in the background. The pool's water shimmers under the sunlight, reflecting the blue sky and scattered clouds.

Guesthouse in Lenox

4.93 out of 5 average rating, 366 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.