We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

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.

0 of 0 items showing

1 of 3 pages

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, 259 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 panoramic view captures the snowy landscape from the condo, showcasing ski trails on the mountains in the background. The foreground features a plaza with chairs arranged around a fire pit, with skiers and snowboards visible along the paths.

Condo in Hancock

4.98 out of 5 average rating, 47 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.

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, 26 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, 167 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 surrounded by fall foliage with hot tub

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, 224 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 a cozy mountain cabin is shown, featuring a mix of wooden and siding materials. A grassy front yard is bordered by a wooden fence, and trees are visible in the background. The sky is bright with clouds, creating a welcoming ambiance.

Home in Hancock

5 out of 5 average rating, 35 reviews

Cozy Ski Cabin in Berkshires Resort

Cozy Ski-In/Ski-Out Cabin at Jiminy Peak – Perfect for Couples, Friends & Families Escape to the heart of the Berkshires at our charming single-level cabin nestled within the Jiminy Peak Ski Resort. Whether it’s a romantic retreat, a fun trip with friends, or a family vacation, our home is the perfect base to explore everything the region has to offer—from outdoor adventures, hiking, and lake swimming to mountain rides and world-class arts, music, and cultural events.

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, 163 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 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, 378 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.

Home in Hancock

4.93 out of 5 average rating, 30 reviews

Family Lodge at Jiminy Peak - Pools & Adventure

Escape to the Berkshires this summer in our spacious 4BR/3BA townhome at Jiminy Peak! Perfect for families, with 2 living rooms, a fully equipped kitchen, and a large Trex deck with mountain views. Enjoy resort perks like outdoor pools, tennis, hiking trails, mountain coaster, and ropes course—all just steps away. With plenty of space and nonstop adventure, it’s the ultimate summer getaway for families and friends!

A living area features a beige sofa with cushions, positioned beside a dark wood coffee table. Natural light enters through a large window with tan drapes, offering a view of grassy landscaping. A simple lamp stands next to the sofa, enhancing the cozy ambiance.

Condo in Hancock

4.9 out of 5 average rating, 71 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

Rent your very own condo in the Country Inn at Jiminy Peak Mountain Resort.This unit is just steps away from the entrance and your ski locker. Ski in/out and never have to move your car! Spectacular view of the mountain from your windows, close to all the amenities the resort has to offer. The resort offers a year-round heated pool, 2 hot tubs, a gym, fireplace lounge and restaurants. The perfect mountain escape.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations with great services and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

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 well-lit living area features large windows allowing natural light, with a cozy plaid sofa and two armchairs positioned around a modern fireplace. A rustic wooden coffee table is placed in the center, complementing the warm tones of the room.

Home in Hancock

4.85 out of 5 average rating, 13 reviews

Beautiful 4 Bedroom Townhouse in the Berkshires

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, 19 reviews

Private chalet | hot tub, shuttle & ski home trail

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

Top guest favorite

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, 7 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

Top guest favorite

The exterior of the house features a two-story structure with gray siding and a steeply pitched roof. A charming lamppost stands in front, alongside landscaped yard with flowering plants. The entrance is highlighted by a welcoming porch, and ample parking space is visible in front of the house.

Home in Hancock

4.97 out of 5 average rating, 29 reviews

Family getaway! Private 4 BR Home on Jiminy Peak

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

A comfortable living area features a stone fireplace with a glowing fire. Two armchairs with patterned upholstery sit nearby, complemented by a wooden coffee table. Natural light fills the space through a large window, enhancing the inviting ambiance.

4.9 out of 5 average rating, 52 reviews

The Slope Side Lodge, Ski off w/ Fireplace!

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, 242 reviews

Mt Snow Ski In/Out at Seasons

Top guest favorite

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, 351 reviews

Private Cottage/Mountain Views/Trails/Fire pit

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.

4.94 out of 5 average rating, 72 reviews

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

Top guest favorite

5 out of 5 average rating, 62 reviews

Four Seasons Slope-side Getaway at Mount Snow

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.

4.92 out of 5 average rating, 83 reviews

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

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, 114 reviews

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

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

4.89 out of 5 average rating, 35 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

Top guest favorite

A spacious living area features a brick fireplace, complemented by a comfortable leather sofa and armchair. Natural light enhances the room, highlighting a wall-mounted TV and decorative elements. A loft area is visible above, adding dimension to the space. A game table is included for entertainment.

4.86 out of 5 average rating, 14 reviews

Cozy 2BR + Loft Near Mt. Snow – Sleeps 8

A recently updated kitchen features dark cabinetry and stainless steel appliances, including a refrigerator, oven, and dishwasher. Natural light enters through a window above the sink, illuminating the countertops. Kitchen essentials are neatly organized, creating a functional space for meal preparation.

Lovely Polar Bear Lodge! Lots of amenities

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, 154 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

Destinations to explore