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Ski-in/Ski-out vacation rentals in Western Massachusetts

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

Top-rated ski-in/ski-out rentals in Western Massachusetts

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

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A charming treehouse sits elevated on wooden stilts, surrounded by lush greenery. Soft lighting decorates the deck area, creating a warm environment. A gravel path leads to the entrance, while the tranquil pond reflects the evening sky in the background.

Home in South Londonderry

4.86 out of 5 average rating, 159 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

Guest Favorite VERY romantic abode…The Honey Pond Treehouse is made for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…Enjoy private hot tubbing, sauna time, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes or enjoy our own groomed trails for Xcountry & snowshoes & nature walks!! High speed WiFi 🐣

The entrance to the Joab Griffin House features a rich purple door framed by a white façade and classic architectural elements. Two potted plants flank the door, adding greenery to the entrance. An American flag gently waves nearby, enhancing the welcoming atmosphere.

Apartment in West Granby

4.9 out of 5 average rating, 132 reviews

Majestic Farmhouse Private & Peaceful Guest Apt.

Welcome to the most beautiful area of CT! We are a beautiful historic farmhouse set on a private hill tucked away in the foothills of the Berkshires, surrounded by gorgeous farmland and hundreds of acres of land trust and game refuge trails, streams, and waterfalls within a five-minute walk from your door. Enjoy a private apartment in this lovely farmhouse. Here, you'll find cool summer breezes, cozy, warm, sun-filled days, and star-filled skies with the sounds of the brook outside your window.

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, 255 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

Top guest favorite

The living room features a high, vaulted ceiling with large, triangular windows allowing ample natural light. A brick fireplace serves as a focal point, surrounded by a wooden mantel and decorative plants. A dining table sits nearby, and hardwood flooring is complemented by colorful area rugs.

Farm stay in Ashfield

5 out of 5 average rating, 124 reviews

Sunny Chalet Nestled in the Woods of Ashfield

Need some time to recharge surrounded by nature? Whether a group of friends, family or a wedding party - this property will suit all your needs. Access to hiking right out the door and loads of recreational activities such as skiing, swimming, biking. Our high speed WiFi and TV support streaming. Curl up on the couch and bask in the sunlight through the windows. Read a book by the fire. Gaze up at the stars and moon from the deck. Share a meal. A perfect spot for a retreat or family gathering.

A lakefront cottage is positioned among trees, with a spacious lawn leading down to the water. A newly installed dock extends into the lake, while various colorful kayaks and paddle boards are neatly arranged on the grass. The sun sets, casting a warm glow over the scene.

Home in Westminster

4.9 out of 5 average rating, 191 reviews

Lakefront, view of ski mtn, fireplace, sauna

Direct lakefront with panoramic views of Wachusett Mountain (#1 skiing in MA). In the summer, enjoy the kayaks, canoe, paddle-boards, motor boat. In the winter, cozy up next to the fireplace and enjoy a complimentary bottle of wine. In the fall, gaze upon the breathtaking foliage from the sunroom. Outdoor shower, dock, firepit, hammock, bike, washer/dryer, desk, sauna, dishwasher, linens, kitchen amenities. Our other lakefront house is down the road: www.airbnb.com/h/lakefrontmountainview

A cozy fire pit is surrounded by stone, situated in the foreground of a spacious lawn. In the background, a modern chalet features large windows and a combination of wood and stone siding, framed by colorful autumn foliage.

Home in Winhall

4.94 out of 5 average rating, 142 reviews

Summit View Ski and Golf Retreat w/hot tub & Sauna

Summit View Chalet @ Stratton is the ideal VT retreat, Minutes from Manchester, directly across the entrance from Stratton's 27 Hole Championship Golf Course. Beautifully remodeled! Relax in the hot tub on the deck with direct summit views in any season. Enjoy shuttle access to lifts, minutes from snowmobiling, hiking, fine dining and shopping. Comfortable accommodations for 6 adults and 5 children. Perfect for 2 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

A serene lakeside scene features a plush chair by the water, where a golden retriever is comfortably resting. Lush greenery surrounds the lake, and a kayak is seen moored nearby, adding to the tranquil atmosphere.

Cottage in Newbury

4.95 out of 5 average rating, 226 reviews

Large Private Lake House

Spacious lake house with a private beach, directly on Lake Todd in Newbury, NH, located within the Lake Sunapee Region. Fish for bass, pickerel or swim/boat to one of the lake's three islands. Relax on the water or on one of the large decks overlooking the lake. Enjoy local outdoor activities such as hiking, biking, golfing, fishing & kayaking. Mt Sunapee ski area is only 10 minutes down the road. Enjoy ice skating and cross country skiing right out your door in the winter or cozy by the fire.

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, 274 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 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, 159 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 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, 220 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.

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, 342 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 modern cabin is nestled among lush greenery, featuring a wooden exterior and a wrap-around porch. Large windows provide views of the surrounding trees, while the gentle slope of the land leads to a grassy area in the foreground.

Guesthouse in Tivoli

4.91 out of 5 average rating, 183 reviews

Tivoli Star Gazing Cabin

Down a long driveway, set amongst 100 year old trees and meadows, the cabin offers time in the quiet country though only minutes to the lively village of Tivoli. With a wrap around porch for morning coffee, fire fly viewing or star gazing. It has a soaking tub, with a hand held shower. The cabin is part of our family compound of a main house and a small garden hut. Each property has an independent outdoor space for relaxing and privacy.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Western Massachusetts ski-in/ski-out rentals

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

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.

5 out of 5 average rating, 16 reviews

Private chalet tucked in the green mountains

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, 156 reviews

The Pinnacle House at Otis Ridge Ski Area!

Top guest favorite

The game room features a mix of recreational activities with a pool table and a ping pong table. Wooden beams and rustic decor provide a cozy atmosphere. Ample seating is positioned around the room, and a spiral staircase leads to an upper level.

Home in Wilmington

5 out of 5 average rating, 32 reviews

Rustic home near skiing & lakes, walk to downtown

Top guest favorite

A modern chalet is set among snow-covered trees, featuring a spacious deck with a railing. Dark blue exterior walls contrast with white snow, while large windows provide views of the surrounding winter landscape. The sloped roof is lined with fresh snow, enhancing the serene atmosphere.

Home in Londonderry

5 out of 5 average rating, 14 reviews

Modern Chalet: Magic Mountain

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!

The living area features a dark grey couch adorned with decorative pillows, paired with two armchairs. A wooden side table is positioned nearby. Vintage red skis are mounted on the wall, adding a rustic touch. A floor lamp provides soft lighting, while a door to another room can be seen in the background.

Home in Wilmington

4.86 out of 5 average rating, 108 reviews

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts

An aerial view captures the expansive property, showcasing a historic farmhouse, nearby barns, and lush green fields. Surrounding trees and rolling hills create a serene backdrop, with a meandering road providing access to the site. The layout reflects the rustic charm of Twilight Dreams Farm.

Home in Roxbury

5 out of 5 average rating, 65 reviews

Twilight Dreams Farm

Top guest favorite

The spacious living room features a large, sectional grey couch and a white armchair, arranged around a wooden coffee table. A brick wood-burning fireplace is situated against a wooden wall, with a mounted TV above it. The room is illuminated by warm lighting.

4.98 out of 5 average rating, 53 reviews

Spring Getaway @ Mt Snow! Hike, Bike, Sleeps 8.

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

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

4.74 out of 5 average rating, 197 reviews

Berkshire Charm w/ Panoramic views

An open living space features warm wooden walls and high beams, illuminated by natural light from skylights. A red sofa with patterned cushions is positioned near a round dining table. A cozy atmosphere is created with a lamp and decorative items on shelves.

Home in Dummerston

4.96 out of 5 average rating, 130 reviews

The Sugar House

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

A charming white clapboard exterior of the guesthouse is framed by a well-maintained lawn, featuring a variety of colorful flowers and greenery. The inviting front porch is adorned with hanging planters, and the surrounding trees provide a lush, natural backdrop.

Cottage in Pomfret

4.95 out of 5 average rating, 38 reviews

Little House in the Big Woods - Tennis Court

The exterior of a charming red house is shown, nestled among greenery. A spacious deck wraps around the front, offering access to outdoor seating. Lush ferns and bushes create a natural border, while tall trees provide a serene, wooded backdrop.

Apartment in Henniker

4.8 out of 5 average rating, 194 reviews

Birchwood at Stonehenge

A cedar pergola provides a shaded sitting area near the water, with comfortable seating and potted plants. A firepit sits on a stone patio, surrounded by lush green grass and reflections of trees on the calm lake surface.

Cottage in Hollis

4.88 out of 5 average rating, 245 reviews

Lakefront Nature Getaway - Wood fired Cedar Sauna

Lush green hills are highlighted by a cluster of slender trees, including birch, with bright foliage under a clear blue sky. The landscape is dotted with rocks and surrounded by vibrant grass and ferns, creating a serene and inviting natural environment.

Guest suite in Williamsburg

4.82 out of 5 average rating, 11 reviews

Flower Hill Farm Retreat ~ Studio

A rustic barn house is framed by green trees, featuring a bright red metal roof. The wooden exterior has aged gracefully, with windows partially visible. A garden area with flowering plants is noted in the foreground, alongside a small stone wall, set against an expansive green field.

Home in Landgrove

5 out of 5 average rating, 24 reviews

Landgrove Charm - Post and Beam Barn House

Ski-in/ski-out cabin rentals

The exterior of The Grateful Barn features a welcoming entrance with a porch and bright red trim. An American flag and a decorative flag hang next to the door. Lush green grass surrounds the area, contributing to a serene outdoor setting.

4.8 out of 5 average rating, 93 reviews

The Grateful Barn

A spacious interior showcases warm wooden floors and a cozy wood-burning stove at the center. Soft lighting from multiple pendant lamps creates a welcoming ambiance. A dining area with a wooden table and chairs is visible, and rustic details can be seen in the surrounding decor.

Cabin in Londonderry

4.76 out of 5 average rating, 408 reviews

Beautiful Art Studio with hot tub/sauna #1 Airbnb

The wooden cabin is enveloped in a serene winter landscape, with smoke rising gently from the chimney. Snow blankets the ground, and trees dot the backdrop. A front porch extends along the cabin, providing a welcoming entrance. A snowmobile is parked nearby.

Cabin in Woodford

4.96 out of 5 average rating, 147 reviews

Stone's Camp on Stamford Stream

A rustic cabin with a gabled roof is set among tall trees under a clear blue sky. The structure features double doors with windows and a spacious deck, with outdoor furniture stored nearby. The surrounding grass is green and well-maintained.

Cabin in Londonderry

4.67 out of 5 average rating, 437 reviews

The Run-In - Beautiful Country Cabin with Hot Tub

The chalet is showcased amidst vibrant autumn foliage, with large windows allowing natural light to fill the space. A spacious deck with a wooden railing extends from the upper level, while the surrounding trees maintain a tranquil setting.

Cabin in Londonderry

4.88 out of 5 average rating, 75 reviews

Green Mt Getaway: <30m to Dining Parks Mountains

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

5 out of 5 average rating, 4 reviews

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

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.

Cabin in Litchfield County

4.88 out of 5 average rating, 25 reviews

Blackberry Cottage

A spacious living area features honey-hued log walls and exposed wooden beams. Comfortable seating includes a sofa, a leather armchair, and a wooden coffee table. Natural light fills the room through multiple windows, with a staircase leading to the upper loft and a cozy stone fireplace visible in the background.

Cabin in Henniker

4.76 out of 5 average rating, 204 reviews

Cabin: Private Hot Tub, Walk to Pats Peak Ski Area

Destinations to explore