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Ski-in/Ski-out vacation rentals in Jiminy Peak

Find and book unique ski-in/ski-out homes on Airbnb

Top-rated ski-in/ski-out rentals in Jiminy Peak

Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A cozy bedroom features a spacious bed draped in a soft, dark blanket. The walls are adorned with a captivating array of framed artwork, showcasing various styles. A bedside table holds a lamp, and a curtain partially covers a window, allowing natural light to filter in.

Place to stay in North Adams

4.93 out of 5 average rating, 256 reviews

Freemans Grove Benevolent Society Walk to MoCA

Welcome to the Freeman's Grove Benevolent Society! Artist's apartment/gallery with kitchen, bath, one bedroom, and a sleeping nook. It is an open floor plan, for heating purposes there are curtains (no doors) on the bedroom and sleeping nook. Sleeps 4 people comfortably. The walk from MASS MoCA to the house is flat except the last block which is STEEP! The apartment is a flight and a half off the street, so be prepared for some stairs. A truly unique apartment and cabinet of curiosities. #fgbs

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

4.94 out of 5 average rating, 86 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.

A comfortable living area features a gray sofa paired with a stylish floor lamp. Mounted on the wall are two crossed red skis, adding a mountain-themed touch. Soft lighting from twinkling fairy lights above creates a relaxing ambiance in the space.

Home in Wilmington

4.86 out of 5 average rating, 111 reviews

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

Welcome to our ❄newly listed❄lodge style home! HOT TUB✅ Our home is located on private 2.6 acre lot with beautiful views of Mount Snow in the distance. Our home offers easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our home. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in southern Vermont!

The interior of the renovated studio cabin is seen from the kitchenette area. A bed, adorned with a patterned coverlet, is framed by a folding screen featuring floral and landscape designs. Artwork hangs on the walls, adding character to the warm space.

Guesthouse in Becket

4.93 out of 5 average rating, 277 reviews

Country Cabin

Lovely private country setting, air conditioner. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. I only accept advance reservations of 2 nights or more. (You may reserve a single night booking within 5 days of request.) The space is for 2 adults but I'm flexible, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.

Top guest favorite

A spacious living area features a large sectional sofa adorned with textured cushions and a sleek coffee table. Natural light floods through tall windows, illuminating the open-plan layout, which seamlessly connects to the dining area with a wooden table and high-backed chairs.

Townhouse in Hancock

5 out of 5 average rating, 24 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

A modern kitchen features a central island with bar stools, stainless steel appliances, and white cabinetry. Natural light floods the space through a skylight and large windows, highlighting the open layout. A dining area with dark chairs sits adjacent to the kitchen.

Apartment in Charlemont

4.99 out of 5 average rating, 164 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

Our happy place is a 5 minute walk to Berkshire East/Thunder Mountain . An 8 minute walk to the Deerfield River for guided fishing tours with Hilltown Anglers, kayaks, ,whitewater rafting. 10 minute walk to town and shuttle for tubing. A 5 minute drive to local wedding venues. We provide a full kitchen with all cooking essentials, a private picnic area with charcoal grill (charcoal provided). We reside at the single family home on property and we’re excited to share our Suite 23 !

A cozy living area features a tall Christmas tree adorned with lights and ornaments next to a glass-top coffee table. A fireplace with built-in decor sits beneath a mounted television. Velvety blue chairs complement an orange accent pillow on the nearby couch, surrounded by large windows with sheer curtains.

Apartment in Hancock

4.76 out of 5 average rating, 17 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!

A pathway lined with lush greenery leads to a bungalow with a screened-in porch, featuring outdoor seating. The soft sunlight filters through the foliage, creating a serene entrance to the welcoming space.

Home in Williamstown

4.89 out of 5 average rating, 223 reviews

Hollywood Bungalow in the Berkshires #C0191633410

Cool Cozy Rustic Country Bungalow with Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Cable & Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

The exterior of The Country Inn is shown, featuring a covered entrance with a sloped roof and decorative columns. Lush greenery and flowering shrubs frame the front, while the building's muted tones complement the natural surroundings. Nearby parking spaces are visible under an overcast sky.

Vacation home in Hancock

4.96 out of 5 average rating, 26 reviews

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.

The front of the house is framed by lush greenery and a vibrant red maple tree. A welcoming red staircase leads to the entrance, while large windows allow natural light to illuminate the interior. The roof is partially covered with clouds, enhancing the outdoor serenity.

4.92 out of 5 average rating, 160 reviews

The Pinnacle House at Otis Ridge Ski Area!

Otis is the best town for a visit to the Berkshires. It is close to all the places you would want to visit like Jacob's Pillow, Tanglewood, Norman Rockwell Museum to start with. It is also close to hiking trails, swimming, shopping and great restaurants. This wonderful three plus bedroom home is located on the backside of Otis Ridge Ski Area. Wake up and take a walk on the ridge or just sit outside and have your morning beverage with the woods surrounding you.

A bright living space features a white sofa with light striped cushions, complemented by a wooden coffee table. A dining area with a light wood table and chairs is present. Large glass doors open to a scenic outdoor view, enhancing the open and airy ambiance.

Home in Germantown

4.97 out of 5 average rating, 346 reviews

Private Cottage/Mountain Views/Trails/Fire pit

A Unique Modern Cottage with Stunning Views / A Spa like Bathroom/ A Charming Gas Fireplace/ Fully equipped Chef's kitchen/Soapstone countertops/New premium appliances. Total Privacy High ceilings, hand plastered walls, antique doors. Glass French doors open to a private deck Enjoy big Catskill Mountain and seasonal Hudson River views. The large bath has a tiled glass door shower and a soaking tub. A Fieldstone fire pit overlooks the Catskills!

A rustic wooden cabin sits in the snow-covered landscape, framed by trees and a soft sunset sky. The cabin is equipped with a sloped metal roof and features a surrounding deck. A fire pit is positioned in the snowy foreground, adding to the cabin's serene atmosphere.

Cabin in Woodford

4.84 out of 5 average rating, 376 reviews

400+ Airbnb Visits: Incredible Mountain Cabin

Our cabin is off the grid, NO running water (read this twice) or indoor bathroom, but it’s comfortable and has been enjoyed by 100’s of Airbnb travelers. There is electricity, but this cabin takes an adventurer in the winter months. Winter Stays take work! Don’t be surprised of shoveling and bringing in your gear! Our reviews speak for how great rental is for people, thank you for considering a stay at our cabin.

Vacation rentals for every style

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Popular amenities for Jiminy Peak ski-in/ski-out rentals

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

A tranquil exterior view of a single-story house, framed by lush greenery and vibrant flowers. A gravel path leads to the front door, which is flanked by a small set of stairs. Two satellite dishes are visible on the roof among the trees.

Home in Stephentown

4.81 out of 5 average rating, 83 reviews

A Magic Spot: Booking year round.

A blue wooden chalet is surrounded by greenery, featuring large glass windows that provide views of the interior. A small outdoor deck leads to a hot tub, positioned against the backdrop of vibrant autumn foliage.

4.89 out of 5 average rating, 18 reviews

Private chalet tucked in the green mountains

A snow-covered landscape is visible, with trees lining the sides of a roadway. The hills in the background are partially obscured by clouds, suggesting a serene winter atmosphere. Several homes and parked cars can be seen along the road.

Home in Hancock

4.96 out of 5 average rating, 23 reviews

Condo on the mountain

A spacious two-story house with a dark wooden exterior is visible, featuring a private balcony adorned with American flags. Two garage doors are present below the balcony, and a well-maintained driveway leads to the entrance, providing an inviting approach surrounded by greenery.

Home in Hinsdale

5 out of 5 average rating, 3 reviews

Berkshire Lake-side Retreat

Top guest favorite

Home in Wilmington

5 out of 5 average rating, 34 reviews

Rustic home near skiing & lakes, walk to downtown

An open living space features a cozy seating area with a large sectional sofa facing a stone fireplace. A dining table is positioned nearby, surrounded by black chairs. Natural light floods the room through oversized windows, showcasing a Christmas tree adorned with decorations.

Home in Wilmington

4.89 out of 5 average rating, 28 reviews

Brand new, 5 BR, next to Hermitage Club&Hermt Inn

Home in Hancock

4.93 out of 5 average rating, 28 reviews

Family Lodge at Jiminy Peak - Pools & Adventure

A historic red farmhouse and adjacent barn are set against a clear blue sky, surrounded by lush green grass. Stone pathways lead to the house, highlighting the inviting porch, while vibrant foliage borders the property.

Home in Whitingham

4.93 out of 5 average rating, 70 reviews

The Amos Brown House.

Family-friendly, ski-in/ski-out home rentals

A cozy living area is highlighted by a stone fireplace, featuring firewood neatly stacked beside it. A flat-screen TV is mounted above the mantel, with built-in cabinets on either side. A sectional sofa and wooden coffee table provide comfortable seating for relaxation.

5 out of 5 average rating, 24 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

A detailed map illustrates the layout of the Mount Snow area. The Seasons Condominiums are highlighted with a red circle, showcasing proximity to ski trails and nearby facilities, including the Sundance Base Lodge and other essential amenities for visitors.

4.89 out of 5 average rating, 111 reviews

Seasons Condo @ Mt Snow (Ski-in/out, hike, bike)

A living room features a large stone fireplace with a wood storage basket beside it. A comfortable sofa with decorative pillows faces a wooden coffee table. Natural light floods the space through a large window, complemented by a nearby area rug.

4.87 out of 5 average rating, 241 reviews

Mt Snow Ski In/Out at Seasons

Top guest favorite

A comfortable living space features a warm-toned sofa, wooden tables, and a dining area with a large table and six chairs. Natural light filters through the window adorned with dark curtains, creating a bright and inviting atmosphere.

Apartment in Dover

4.97 out of 5 average rating, 31 reviews

Mt Snow 2 Bdrm Condo - Free Shuttle

A spacious living area is introduced, featuring a stone fireplace and a large sectional sofa arranged around a coffee table. A dining table and chairs are positioned nearby, with natural light filtering through large windows adorned with curtains.

4.96 out of 5 average rating, 68 reviews

Condo w/ great amenities 4-seasons! Ski in Ski out

Top guest favorite

5 out of 5 average rating, 61 reviews

Four Seasons Slope-side Getaway at Mount Snow

A modern, architect-designed house is nestled among lush greenery and towering trees. A gravel driveway leads to the front entrance, framed by shrubs and flowering plants, while large windows reflect the surrounding natural beauty.

4.99 out of 5 average rating, 68 reviews

Modern House, Wild Gardens, Peaceful Creeks

The kitchen features modern cabinetry with a combination of dark and light finishes. A farmhouse sink is positioned beneath a window, complementing stainless steel appliances, including a gas range and dishwasher. A spacious countertop offers ample preparation area.

4.91 out of 5 average rating, 82 reviews

FULLY renovated 1 bed/1 bath ski in-out condo!

Ski-in/ski-out condo rentals

The exterior of the resort is highlighted by a wooden gazebo surrounded by lush greenery. The three-story building features gabled roofs and multiple balconies, with warm lights illuminating the windows during twilight.

Condo in Hancock

4.89 out of 5 average rating, 9 reviews

Condo Resort at Jiminy Peak Ski Mountain's Base

A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.

Condo in Hancock

4.95 out of 5 average rating, 61 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

A ski lift station is visible, featuring a large two-story building with green shutters. Snow-covered ground surrounds the area, where several people prepare for skiing. A snowmobile and ski equipment are located nearby, while a snow-covered slope rises in the background.

Condo in Hancock

4.88 out of 5 average rating, 34 reviews

Unique - Country suite @ Jiminy Peak

A comfortable living area is presented with a plaid chair and a sofa, complemented by a coffee table. Natural light fills the space through a large window with elegant drapery. A flat-screen television is positioned nearby, enhancing the relaxation setting.

Condo in Hancock

4.88 out of 5 average rating, 32 reviews

Jiminy Peak Apartment

The Crafts Inn features a distinctive historic facade with multiple gabled roofs and decorative shutters. Red, white, and blue bunting is displayed on the front porch. Well-maintained landscaping includes green grass and shrubbery, creating an inviting entrance to this National Historic Landmark.

Condo in Wilmington

New place to stay

Crafts Inn in Vermont 1br suite, Saturday check-in

The exterior of a large, two-story building is showcased against a snowy backdrop, with tall trees partially visible in the foreground. The building features arched entryways and multiple windows, while the sloped ski hill rises in the background, indicating proximity to winter sports.

Condo in Hancock

4.6 out of 5 average rating, 153 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

Icicles hang from a structure in the foreground, with a view of snow-covered ski slopes illuminated by soft lights in the distance. The landscape is blanketed in fresh snow, creating a serene winter atmosphere.

Condo in Hancock

5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

A cozy living area features a comfortable sofa grouped with an armchair and a coffee table. A large window allows natural light to illuminate the space, while curtains frame the view. A television is positioned nearby, enhancing the room's functionality.

Condo in Hancock

4.9 out of 5 average rating, 10 reviews

Ski-in/Ski-Out on Jiminy Peak

Destinations to explore