Ski-in/Ski-out vacation rentals in Hancock

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.

4.93 out of 5 average rating, 269 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 spacious living area is depicted with a large sectional sofa and a wooden coffee table. A stone fireplace serves as a focal point, featuring a mounted TV above. Natural light streams through the windows, illuminating bookshelves filled with games and books, while a stack of firewood is neatly arranged beside the fireplace.

4.92 out of 5 average rating, 102 reviews

Slopeside Condo @ Seasons on Mt Snow (Ski-In/Out)

Escape to the mountains & stay in our fully equipped 3 bedroom (ski in/out) condo. Enjoy the wood burning fire (wood provided), smart TV & boardgames as well as the fabulous Seasons on Mt Snow facilities where you can relax in a hot tub, pool or sauna. Our ski in/out location is the best on the mountain, between the main face & Carinthia Freestyle Park! See below for info on activities in the warmer months which include hiking, biking, scenic rides, lakes, golf, camp, a spa & the fall colors!

4.87 out of 5 average rating, 136 reviews

A cozy living area features a dark gray sofa with decorative cushions, complemented by two wooden armchairs. A timber-framed window offers a view of the outdoors. A coffee table holds a small centerpiece, and vintage skis are mounted on the wall above the seating.

Home in Wilmington

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!

4.99 out of 5 average rating, 102 reviews

An open living area showcases a wood fireplace with a striking red exterior. A spacious dining table is set for meals, complemented by cozy seating arrangements. Large glass doors provide views of the surrounding trees, inviting natural light into the room.

Chalet in Charlemont

StrautmanHaus: All-Season Chalet at Berkshire East

Welcome to StrautmanHaus, a Bavarian style A-Frame home, nestled at the base of Berkshire East Mountain Resort. This charming chalet is newly renovated, with 4 beds/2 baths/4 decks and stunning views that sleeps 10! Surrounded by mature growth pine trees, the property offers a perfect combination of privacy and ski-on/off access to Berkshire East. In the summer & fall, you have on-site access to the resort’s mountain biking/white water rafting/zip line/mountain coaster & aerial adventure park.

4.92 out of 5 average rating, 127 reviews

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

Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

4.92 out of 5 average rating, 108 reviews

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.

4.99 out of 5 average rating, 186 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.

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 !

A spacious living area features a large sectional sofa adorned with decorative cushions. A wooden coffee table sits in front, with a lamp beside it. A dining area is visible, accompanied by a window allowing ample natural light and a view of the surrounding trees.

4.94 out of 5 average rating, 106 reviews

Cozy Mt Snow Ski In / Out

Directly on the mountain. Ski right back to door. Less than 2 minute walk to the trails. Full kitchen, dishwater, washer/dryer, microwave. Fireplace with free wood. Large screen TV in living room and 1 in each bedroom. Ground floor with private deck with tables and chairs for relaxing. Free parking. Condo across the hall is also available for larger groups. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.

5 out of 5 average rating, 144 reviews

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.

4.9 out of 5 average rating, 232 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 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.

4.92 out of 5 average rating, 174 reviews

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.

4.93 out of 5 average rating, 111 reviews

MountSnow ski on/off condo in Vermont

Pool and Sports Center is open. Hours vary by day BBQ available for use by the outdoor pool pavilion On Mount Snow, Across from the Tin Lizzy trail leading to the Sundance Base Lodge and access to the Seasons Pass trail leading back to the condo. Very unique Condo in seasons as it has high vaulted ceilings. Condo is a 2 bedroom, 2 bathroom with 2nd bedroom on 2nd floor. Plenty of tennis and pickleball courts Best parking on the mountain

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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

4.82 out of 5 average rating, 88 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.

5 out of 5 average rating, 11 reviews

Home in Dover

Ski In/Ski Out Mount Snow Condo.

A welcoming living area features two light-colored sofas adorned with various decorative cushions. A wooden coffee table sits at the center, surrounded by a floor lamp and a stand displaying decor items. A television is positioned nearby, enhancing the comfortable atmosphere.

4.25 out of 5 average rating, 16 reviews

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Pe

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.

4.96 out of 5 average rating, 26 reviews

Condo on the mountain

5 out of 5 average rating, 8 reviews

Mountainside Condo w/ Private Access To Ski Slope

5 out of 5 average rating, 51 reviews

Two paddleboards rest on a smooth rock shoreline, overlooking a serene lake. Lush greenery surrounds the water, and a clear blue sky with scattered clouds adds to the tranquil atmosphere.

Home in Wilmington

Game Room, near skiing and lake, walk to downtown

4.77 out of 5 average rating, 156 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

4.89 out of 5 average rating, 27 reviews

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

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

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

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.

4.79 out of 5 average rating, 14 reviews

Beautiful 4 Bedroom Townhouse in the Berkshires

Apartment in Hancock

4.74 out of 5 average rating, 31 reviews

Central Berkshires Artsy Loft with Pool & Hot Tub

Home in Plainfield

5 out of 5 average rating, 3 reviews

A Quaint country charm - Private house at RV camp

5 out of 5 average rating, 11 reviews

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

Berkshire Lake-side Retreat

A rustic wooden sign hangs from a post, displaying the name 'Knoll Rock' and a pineapple emblem. Lush greenery and trees frame the scene, with a gravel road leading away from the sign, suggesting a peaceful, natural setting.

Guest suite in Canaan

5 out of 5 average rating, 9 reviews

Knoll Rock Studio - Best of the Berkshires.

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.

4.93 out of 5 average rating, 131 reviews

Blackberry Cottage

4.84 out of 5 average rating, 199 reviews

A spacious living area features a rich brown leather sofa paired with light-toned armchairs. A wooden coffee table complements the decor. Above, a loft area overlooks the space, with a staircase leading to it. Natural light fills the room through nearby windows.

Chalet in Dover

4BD 2BA | Mount Snow VT | Ski-Back Trail | Shuttle

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, 32 reviews

Family getaway! Private 4 BR Home on Jiminy Peak

Ski-in/ski-out condo rentals

4.94 out of 5 average rating, 71 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.

Condo in Hancock

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

A cozy living area is designed with a comfortable sofa adorned with patterned cushions. A wood coffee table occupies the center, complemented by a lamp on each side. Natural light floods the space through large windows and a door leads to a balcony.

4.88 out of 5 average rating, 95 reviews

Cute, Cozy Condo at the base of Mount Snow

A cozy living area features a large sectional sofa and a wooden coffee table, set on a spacious area rug. Natural light filters through a large window, with a stone fireplace and a mounted television providing warmth and entertainment.

4.95 out of 5 average rating, 61 reviews

Ski On/Off 2BR w/Pool, Fireplace & Arcade

4.86 out of 5 average rating, 37 reviews

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

Jiminy Peak Apartment

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.

4.95 out of 5 average rating, 99 reviews

Great Amenties-Seasons Condo gym-sport center-pool

A tranquil lake reflects the vibrant colors of autumn foliage, showcasing a mix of red, orange, and yellow trees. A small island featuring a cluster of trees and shrubs emerges in the foreground, surrounded by calm waters and a gentle green grass shoreline.

5 out of 5 average rating, 72 reviews

Four Seasons Slope-side Getaway at Mount Snow

4.61 out of 5 average rating, 162 reviews

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

Jiminy Peak Country Inn 1 Bedroom Suite

A modern kitchen is showcased with white cabinets and a dark granite countertop. Stainless steel appliances, including a refrigerator and stove, are visible. A dining table with wooden chairs is situated nearby, while a cozy living area can be seen through the open layout.