Holiday houses in Jiminy Peak

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Top-rated holiday rentals in Jiminy Peak

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Top Guest favourite
A snowy landscape is presented, showcasing ski slopes and a bustling scene below. A quaint building serves as a backdrop, surrounded by skiers and snowboarders. Tables and chairs are visible, along with ski equipment neatly arranged, highlighting the active atmosphere accessible from the condo.
Condo in Hancock
4.95 out of 5 average rating, 92 reviews

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1

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.

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Apartment in Hancock
5 out of 5 average rating, 3 reviews

Mountain Getaway Suite Ski OnOff Jiminy Peak - Ful

You want to pop out of bed, walk down hall, and be right on the mountain This 1BR 1 BA Third Floor Unit Charming Mountain Decorated Suite right by the entrance boasts gorgeous views and 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, including 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 h

Top Guest favourite
Apartment in North Adams
4.96 out of 5 average rating, 654 reviews

Steps to MoCA Near SKI: 2bd + SAUNA!

Near ⛷️ SKI resorts: Jiminy Peak, Berkshire East Mountain and others. A large, private 2-bedroom apt at the Small Mansion of Chase Hill Estate. Outdoor Sauna! Just a 5 minute-walk to MASS MoCA & downtown restaurants, 10 mins drive to Williams College & Clark. Whimsically restored (fast Wi-Fi & great water pressure!) and part of @chasehillartistretreat ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates available beyond what the calendar shows—contact us!

Top Guest favourite
A peaceful scene reveals a winding road leading through a residential area with well-maintained homes. Snow-covered mountain slopes are visible in the background, flanked by trees that display early signs of changing seasons.
Townhouse in Hancock
4.92 out of 5 average rating, 101 reviews

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

Top Guest favourite
The cozy upstairs studio features a queen bed adorned with patterned bedding. Two windows allow natural light to illuminate the space, highlighting the exposed wooden beams and rustic charm. A comfortable chair and a TV are positioned nearby, creating a welcoming relaxation area.
Cabin in Canaan
4.99 out of 5 average rating, 260 reviews

Rustic Barn Studio Apartment

Built from a saved, moved, & reconstructed 1850s- era barn from a former local dairy farm, this upstairs studio space features views of the Berkshire Mountains and walking paths on the 5 acre grounds. 20 mins from Jiminy Peak. 20 mins from Tanglewood Music Center. The space has a queen bed, sofa, kitchen area with fridge, sink, oven, stove, microwave, Keurig and coffee, toaster, and cooking essentials. **EV Charging Station coming sometime summer of 2023. We'll update when available.

Guest favourite
An outdoor deck is presented with a large wooden table surrounded by chairs. Colorful cushions add comfort, and potted flowers brighten the space. Soft string lights hang above, illuminating a hammock and lounge chairs nearby, all set against a backdrop of lush greenery.
Guest suite in Hancock
4.82 out of 5 average rating, 197 reviews

Cozy apartment near Jiminy Peak

Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.

Top Guest favourite
A wooden structure with a deck extends into the greenery, framed by tall hop poles. The building features a large front porch, inviting outdoor seating, and an entrance accentuated by surrounding trees and a grassy area leading up to it.
Apartment in Petersburgh
4.89 out of 5 average rating, 209 reviews

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Open space includes living/dining/work space & bedroom; bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed (extra twin mattress beneath). HD TV, wifi, private deck, kitchenette with mini fridge, microwave, toaster oven, hot tea kettle and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

Guest favourite
A snow-covered entrance showcases a wooden sign featuring 'SMITH UNITS 1061 - 1064.' The residential building, adorned with white siding, includes a window unit air conditioner protruding from the wall. Surrounding shrubs are blanketed with fresh snow.
Townhouse in Hancock
4.83 out of 5 average rating, 96 reviews

Beautiful Jiminy Peak Townhome Family Friendly

Leave the city behind and come work remotely from our 3 bedroom, 2 bathroom newly renovated townhome. Whether you're visiting the Berkshires area in the winter for skiing at Jiminy Peak, or you're seeking summertime adventures on the lakes and the hiking trails, this 3 level home with puts you right in the middle of the action. Perfect for families, this rental is located in a community just a mile (3 minute drive) from the mountain and managed by Moresi Property Management.

Top Guest favourite
A two-story home is depicted, featuring a grey wooden exterior with multiple windows. A wooden deck with stairs leads to the entrance, surrounded by green grass and vibrant yellow flowers. The clear blue sky complements the inviting structure.
Farm stay in Pittsfield
4.99 out of 5 average rating, 284 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 favourite
A cozy living area features a light grey sofa paired with a wooden coffee table. An accent chair with a textured throw sits beside a basket. A large cow print hangs on the wall, with two framed pieces nearby. A patterned rug covers the floor.
Apartment in Bennington
4.95 out of 5 average rating, 178 reviews

Cooper's Place

Small bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with VT flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas.

Top Guest favourite
The open living area showcases a modern curved sectional sofa in dark leather, adorned with cream and patterned pillows. A sleek chandelier hangs from the high ceiling, complemented by a wall-mounted TV and a wooden fireplace. Large sliding doors lead to the outdoor patio.
Home in Hancock
4.95 out of 5 average rating, 42 reviews

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!

Top Guest favourite
The living area features a comfortable seating arrangement with a patterned armchair and a light-colored sofa accented by a vibrant throw. A side table is positioned next to the sofa, and a wall clock adds a decorative touch, while wooden flooring enhances the cozy ambiance.
Apartment in Troy
4.96 out of 5 average rating, 124 reviews

Adorable Apartment - Near Emma Willard, RPI, Troy

Welcome to Cheri's house! You'll enjoy a private 1 bedroom apartment including a full size bed in the bedroom, living room with pull-out sofa and smart TV, full kitchen, bathroom and bonus work space or dining room. Off street parking, free WiFi and breakfast included. My home is a quick 5 min walk to Emma Willard School, 1.5 miles to RPI, and 2 miles to Russell Sage College. The unit is on the 2nd floor of an owner-occupied house. Please ask me any questions!

Popular amenities for Jiminy Peak holiday rentals