Ski-in/out rentals in Jiminy Peak Mountain Resort

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.

4.93 out of 5 average rating, 103 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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Place to stay in North Adams

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.

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

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4.94 out of 5 average rating, 282 reviews

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.

4.95 out of 5 average rating, 73 reviews

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

Jiminy's GEM is everything you're looking for! The location is absolutely prime- steps from the highspeed 6pk lift with your balcony overlooking the beautiful mountain & apres fire pit. Enjoy 3 bdrms/3 full baths with enough beds to accommodate numerous families, sleeping a total of 10 people. Take advantage of a heated pool, hottub & gym when you're not enjoying the mountain. Summer and Leaf Peeping season are equally as entertaining and enjoyable. Let us make your trip better than imagined!

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The exterior of the chalet features a charming front porch adorned with a railing, surrounded by colorful autumn foliage. A gravel parking area is visible, leading to a well-maintained lawn with seasonal flowers. Towering trees provide a natural backdrop to the serene setting.

4.85 out of 5 average rating, 60 reviews

Comfortable Berkshires retreat on mtn resort, SISO

Once a retreat for an NYC real estate family, this grand yet comfortable place in Jiminy Peak has retained the feel of a chalet: perfect after a ski/hike/bike through the beautiful mountains around it. 4 bdrs allow your group to space out, and a great room with 20 foot high ceilings extends through the dining area. Convenient to many Berkshires spots (Tanglewood, museums, etc.), a 2nd living room, fireplace, jacuzzi, and access to slopes, hot tubs, heated pool & gym complete the perfect getaway.

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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.

4.62 out of 5 average rating, 169 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

A privately owned, older unit within Jiminy Peak's Country Inn. Located in the Berkshires, the inn is at the base of the ski slope. This unit is on the 1st floor of the last building which means you can ski to your doorstep if there's lots of snow (harder getting to the lift) . A locker room is at the end of the building to secure your equipment (key provided). The resort offers a year-round heated pool, 2 hot tubs, a gym, fireplace lounge and seasonal restaurants. Come enjoy the mountain!

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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.

4.92 out of 5 average rating, 115 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.

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The exterior of a townhome is shown covered in fresh snow, with a covered porch and white railing. Flanked by evergreen trees, the structure features a gabled roof and a single round window above the front entrance, adding character to the picturesque winter scene.

5.0 out of 5 average rating, 43 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!

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5.0 out of 5 average rating, 203 reviews

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.

Flat in Charlemont

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 !

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4.9 out of 5 average rating, 243 reviews

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

Hollywood Bungalow in the Berkshires #C0191633410

Cool Cozy Rustic Country Bungalow with 7.1 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, 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.

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5.0 out of 5 average rating, 12 reviews

3BR @ Jiminy Peak | 4-Season Berkshires Retreat

4-season Berkshires retreat at the base of Jiminy Peak Mountain. PRIME ski-in/ski-out in winter, mountain adventure park in summer & fall. The 3BR/2BA JPeak Condo at JJ's Lodge sleeps 8–10 in 1 King, 1 Queen, 2 Bunk Beds (Twins over Fulls) — steps from ski lifts, trails, Alpine Slide, mountain coaster & summit chairlift. Country Inn amenities (pool, hot tubs, gym, game room) open year-round. Village restaurants, fire pits, coffee shop & ski shop open ski season.

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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.

4.92 out of 5 average rating, 86 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.

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A welcoming family room is presented, featuring two black leather sofas adorned with throw pillows. A wooden coffee table sits in the center, surrounded by a soft area rug. A flat-screen TV is mounted above a wood-burning fireplace, with natural light streaming in through multiple windows.

4.92 out of 5 average rating, 39 reviews

Newly Renovated Mountainside Townhome, Jiminy Peak

Short 2-minute walk to Jiminy Cricket lift, a beautifully renovated 2 bedroom/2 bathroom townhome in Mountainside at Jiminy Peak. Space boasts an open kitchen and family room layout w/ brand new appliances and quartz countertops. A warm wood-burning fireplace in family room creates a cozy atmosphere. Family room slider opens onto private back deck w/ views of the mountain and slopes.

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Popular amenities for ski-in/out rentals near Jiminy Peak Mountain Resort

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/out house rentals

4.77 out of 5 average rating, 93 reviews

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

A Magic Spot: Booking year round.

ValueFamilyHospitality

4.76 out of 5 average rating, 174 reviews

Two white Adirondack chairs are positioned on a green lawn, facing a sunset over a serene water view. A round fire pit stands nearby, surrounded by lush trees. Soft sunlight filters through the leaves, creating a peaceful outdoor atmosphere.

Home in Troy

Riverfront Rustic 1824 Mansion

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4.96 out of 5 average rating, 27 reviews

Condo on the mountain

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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.

4.97 out of 5 average rating, 33 reviews

Family getaway! Private 4 BR Home on Jiminy Peak

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The living area features a stone fireplace as a focal point, with a wall-mounted television above. Ambient lighting is provided by two table lamps and overhead fixtures, illuminating the comfortable seating arrangement comprised of a couch, armchair, and leather chair, all positioned around a central coffee table.

4.9 out of 5 average rating, 30 reviews

Mountainside: Large 3-level Jiminy Peak Home

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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.

4.98 out of 5 average rating, 42 reviews

Cozy Cabin in the Berkshire Resort

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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.

4.73 out of 5 average rating, 15 reviews

Beautiful 4 Bedroom Townhouse in the Berkshires

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4.96 out of 5 average rating, 46 reviews

A guest lodge is nestled among lush greenery and vibrant flower beds. Colorful blooms in various hues encircle the property, enhancing the natural landscape. Trees provide shade nearby, while a clear blue sky can be seen in the background.

Home in Hawley

Stump Sprouts Lodge

ValueFamilyCleanliness

Family-friendly, ski-in/out home rentals

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.

4.87 out of 5 average rating, 38 reviews

Jiminy Peak Apartment

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4.78 out of 5 average rating, 40 reviews

Flat in Hancock

Artsy Leaf Peeping Loft with Pool & Hot Tub

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4.73 out of 5 average rating, 216 reviews

An old agricultural tool sits in a grassy field, its wheels complementing the expansive landscape. In the background, vibrant hues of sunset illuminate the sky, casting a soft glow over the lush green foliage and distant hills.

Guest suite in Lee

Berkshire Charm w/ Panoramic views

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5.0 out of 5 average rating, 11 reviews

THE SLOPE slope-view Country Inn 1BR w/heated pool

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A spacious living area features a sectional gray couch adorned with colorful throw pillows. A wooden coffee table sits center stage, complemented by an area rug. A modern lamp provides soft lighting, while a fireplace maintains a cozy ambiance. Abstract art hangs on the wall.

5.0 out of 5 average rating, 7 reviews

Five-Star Family Friendly Townhouse

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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.

4.75 out of 5 average rating, 16 reviews

Ski-in/Ski-Out on Jiminy Peak

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A comfortable living room is presented with two sofas adorned with festive cushions. A coffee table is centered on a cozy area rug, while a television sits atop a media console. Large windows framed by dark curtains allow natural light to fill the space.

4.79 out of 5 average rating, 42 reviews

Unique - Country suite @ Jiminy Peak

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Flat in Hancock

Cozy Ski in/Out Condo - King Bed & Hot Tub

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5.0 out of 5 average rating, 3 reviews

Ski-in/out cabin rentals

Cabin in Litchfield County

A cozy living area features a brown leather sofa with white throw pillows, positioned beside a window that allows natural light. A wooden coffee table sits atop a blue and white woven rug, complemented by a comfortable armchair. Shelves display decorative items and fresh flowers add a welcoming touch.

Blackberry Cottage

LocationValueOutdoor spaces

4.93 out of 5 average rating, 168 reviews

4.85 out of 5 average rating, 393 reviews

Cabin in Woodford

400+ Airbnb Visits: Incredible Mountain Cabin

LocationValueOutdoor spaces

4.86 out of 5 average rating, 427 reviews

The cabin's exterior is surrounded by lush greenery, showcasing wooden siding and a well-maintained deck. Outdoor seating is provided on raised steps, while a patio area features a small table and chairs. An umbrella offers shade for relaxation during sunny days.

Cabin in Otis

Cozy cabin in the Berkshires

LocationValueIndoor spaces

4.94 out of 5 average rating, 35 reviews

Cabin in New Salem

Rustic cabin with A/C at historic orchard & cidery

LocationFamilyIndoor spaces

5.0 out of 5 average rating, 10 reviews

The dining area features a wooden table set with plates and glassware, facing large windows that offer expansive views of the lush green landscape and distant hills. A stone patio is visible outside, with an inviting seating arrangement, and the natural light brightens the space.

Cabin in Shelburne

Summit Retreat:2BR/2Bath Rustic Beauty + Yoga Room

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Ski-in/out apartment rentals

4.9 out of 5 average rating, 125 reviews

Mountain Getaway @Seasons on Mount Snow Ski-In/Out

LocationFamilyAccess

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, 109 reviews

Great Amenities-Season Condo gym-sport center-pool

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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.

4.88 out of 5 average rating, 263 reviews

Mt Snow Ski In/Out at Seasons

LocationFamilyIndoor spaces

4.97 out of 5 average rating, 120 reviews

An open living area features a large wooden dining table surrounded by metal chairs. The kitchen showcases modern appliances and a sleek countertop, while a comfortable seating area is arranged nearby with a sectional couch and coffee table against a textured wall.

Apartment in Stratton

Luxury Stratton condo just steps to the lift!

LocationFamilyDecor

4.92 out of 5 average rating, 128 reviews

Base of M.S. All Seasons Fun. Deck/HotT/Sauna

LocationFamilyView

4.93 out of 5 average rating, 113 reviews

MountSnow ski on/off condo in Vermont

ValueFamilyQuiet

4.98 out of 5 average rating, 59 reviews

The living area features a spacious sectional sofa arranged around a coffee table, complemented by a cozy wood-burning fireplace. Natural light fills the room through large windows, which overlook the snowy landscape. A dining table for six and a media console housing a Smart TV are also present.

Apartment in Stratton

Ski In/Out, Cozy 3Bed condo steps to Village

LocationFamilyParking