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Ski-in/Ski-out holiday rentals in Massachusetts

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

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

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Top Guest favourite
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

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

FamilyLocationHeating

4.94 out of 5 average rating, 279 reviews
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

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.

LocationValueHot tub

4.93 out of 5 average rating, 103 reviews
Guest favourite
Home in Shutesbury

Lakefront Oasis at Lake Wyola

Come enjoy our fully appointed lakefront home on Lake Wyola. With your own waterfront access and 180 degree views from the living, kitchen, dining, and master bedrooms, this comfortable getaway will not disappoint. We are just 20 min from Amherst and 35 min to Northampton with easy access to all of the five colleges. Enjoy morning coffee with flawless views from our wraparound deck. Miles of hiking trails just steps away. Three bedrooms with fully equipped kitchen and open concept living/dining.

FamilyLocationWi-Fi

5.0 out of 5 average rating, 12 reviews
Guest favourite
A outdoor deck features a round dining table and two chairs, positioned under a large umbrella. A side chair rests nearby. The scene is complemented by a colorful seasonal welcome mat, while a view of the expansive green yard and trees is visible in the background.
Apartment in Weymouth

Spacious 1-Bed Apt. in Peaceful Weymouth W/Balcony

Spacious and sunlit 1-bedroom apartment in a peaceful Weymouth neighborhood, featuring a private balcony and relaxing views.Perfect urban retreat for relaxing or working from home, blending quiet natural beauty with excellent proximity to local seaside parks and easy Boston commuting.Open-concept layout featuring oversized windows that flood the apartment with natural light & connect directly to your private balcony offering quiet, peaceful views, perfect for morning coffee or evening unwinding.

FamilyValueAccuracy

4.84 out of 5 average rating, 57 reviews
Guest favourite
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

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

FamilyValueRiver

4.89 out of 5 average rating, 240 reviews
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

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.

FamilyValueNearby

4.92 out of 5 average rating, 115 reviews
Top Guest favourite
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.
Townhouse in Hancock

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!

LocationFamilyDecor

5.0 out of 5 average rating, 43 reviews
Top Guest favourite
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

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 !

LocationFamilyBarbecue

5.0 out of 5 average rating, 201 reviews
Guest favourite
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

Perfect location for a get together with family and friends! This is a one-of-a-kind guest lodge atop a high meadow with magnificent views. 400 acres. Right from our door, you'll find 15 miles of groomed x-c skiing, fat biking, and snowshoe trails in winter, hiking & mountain biking trails in the summer. Sauna, large living rooms. Commercial range in kitchen, large dining room. 10 minutes from Berkshire East, whitewater adventures, canopy tours, mountain biking and more.

ValueFamilyBathroom

4.96 out of 5 average rating, 46 reviews
Top Guest favourite
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

Sunny Chalet Nestled in the Woods of Ashfield

Relax in a quiet sunny chalet located on land with established herbal gardens, offering privacy, space, and a comfortable base for families and small groups visiting Ashfield and the surrounding hills. This pet-friendly three-bedroom home is designed for guests who want a peaceful, rural stay with the reassurance of an attentive host nearby. Whether you’re visiting family, exploring the area, or enjoying time away from the city, the chalet offers room to unwind in a calm setting.

FamilyLocationGetting around

5.0 out of 5 average rating, 154 reviews
Top Guest favourite
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.

ValueFamilyIndoor spaces

4.9 out of 5 average rating, 242 reviews
Top Guest favourite
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.
Home in Otis

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.

FamilyLocationAccuracy

4.92 out of 5 average rating, 178 reviews

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

KitchenWi-FiPoolFree parking on premisesAir conditioning

Ski-in/ski-out house rentals

Superhost
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.
Home in Hancock

Comfortable Berkshires retreat on mtn resort, SISO

FamilyLocationNearby

4.84 out of 5 average rating, 58 reviews
Guest favourite
Home in Hancock

Mountainside Condo w/ Private Access To Ski Slope

LocationFamilyAccuracy

5.0 out of 5 average rating, 11 reviews
Guest favourite
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

Cozy Cabin in the Berkshire Resort

FamilyLocationWalkability

4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Hancock

Condo on the mountain

FamilyLocationSleep quality

4.96 out of 5 average rating, 27 reviews
Home in Worcester

Game Room + Bar Lounge | 35 Min to Boston

FamilyValueCleanliness

4.67 out of 5 average rating, 12 reviewsA 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

Beautiful 4 Bedroom Townhouse in the Berkshires

FamilyLocationHeating

4.73 out of 5 average rating, 15 reviews
Guest favourite
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.
Home in Hancock

Mountainside: Large 3-level Jiminy Peak Home

FamilyLocationAccuracy

4.9 out of 5 average rating, 30 reviewsA charming rustic farmhouse is nestled among vibrant autumn foliage. The house features large windows and a distinctive color. In the foreground, a dog is seen wearing an orange vest, surrounded by colorful flowers and shrubs, creating a serene and inviting atmosphere.
Home in Worthington

A simple kind of paradise

LocationFamilyAccuracy

4.67 out of 5 average rating, 9 reviews

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

Superhost
An outdoor pool area is surrounded by several lounge chairs and umbrellas, offering a view of vibrant autumn foliage on the hills. The pool is partially covered, and a building is visible in the background, enhancing the resort-like atmosphere.
Apartment in Hancock

Mountainside Condo Ski on/off

LocationFamilySkiing

4.84 out of 5 average rating, 44 reviews
Guest favourite
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.
Townhouse in Hancock

Newly Renovated Mountainside Townhome, Jiminy Peak

LocationFamilyNearby

4.92 out of 5 average rating, 39 reviews
Guest favourite
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

FamilyValueDecor

4.73 out of 5 average rating, 216 reviews
Guest favourite
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

Country Cabin

ValueFamilyCleanliness

4.92 out of 5 average rating, 294 reviews
Top Guest favourite
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

LocationFamilyComfort

5.0 out of 5 average rating, 10 reviews
Apartment in Hancock

Artsy Leaf Peeping Loft with Pool & Hot Tub

LocationFamilyHospitality

4.78 out of 5 average rating, 40 reviews
Guest favourite
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.
Townhouse in Hancock

Five-Star Family Friendly Townhouse

LocationFamilyCleanliness

5.0 out of 5 average rating, 7 reviews
Apartment in Hancock

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

LocationFamilyHospitality

5.0 out of 5 average rating, 3 reviews

Ski-in/ski-out condo rentals

Guest favourite
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

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

LocationFamilyView

4.92 out of 5 average rating, 86 reviews
Guest favourite
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

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

FamilyLocationAccess

4.95 out of 5 average rating, 73 reviews
Top Guest favourite
Condo in Hancock

3BR @ Jiminy Peak | 4-Season Berkshires Retreat

LocationFamilyHospitality

5.0 out of 5 average rating, 12 reviews
Guest favourite
A cozy living area is presented, featuring a sofa, armchairs, and a coffee table. Large windows offer natural light, framed by soft curtains. A mirror reflects the space, enhancing the openness. A small dining area with bar stools is situated adjacent to the kitchen.
Condo in Hancock

Large one bedroom, two full bath, full kitchen

LocationFamilySkiing

4.92 out of 5 average rating, 26 reviews
Guest favourite
Condo in Hancock

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

FamilyLocationView

5.0 out of 5 average rating, 10 reviewsThe 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

Jiminy Peak Country Inn 1 Bedroom Suite

FamilyLocationWalkability

4.62 out of 5 average rating, 168 reviewsA 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

Ski-in/Ski-Out on Jiminy Peak

LocationValueCleanliness

4.75 out of 5 average rating, 16 reviews
Guest favourite
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

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2

ValueFamilyQuiet

4.95 out of 5 average rating, 60 reviews

Destinations to explore