Ski-in/Ski-out holiday rentals in Lanesborough

4.89 out of 5 average rating, 111 reviews

SKI IN/OUT @ Mount Snow (Hot Tub & Pool)

Escape to Seasons on Mount Snow & stay in our fully equipped 2 bedroom (ski in/out) condo. Our location is the best on the mountain ... right between the main face & Carinthia Freestyle Park! Enjoy the log burning fire (wood provided), smart TV & boardgames plus the fabulous Seasons on Mount Snow facilities where you can relax in a hot tub, pool or sauna. See below for info on activities in the warmer months including hiking, biking, scenic rides, lakes, golf, camp, a spa & the fall colors!

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, 264 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

5 out of 5 average rating, 136 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

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.

4.86 out of 5 average rating, 117 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!

A cozy seating area features two woven chairs adorned with striped cushions. A small table holds a decorative vase with flowers, set against large windows that frame a vibrant backdrop of autumn foliage outside.

4.91 out of 5 average rating, 114 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.

4.99 out of 5 average rating, 171 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 stone fireplace, featuring a wooden mantel adorned with items, is complemented by a modern television mounted above. The room is painted in a warm yellow hue, while fireside logs are neatly stacked in an iron holder to the side.

4.92 out of 5 average rating, 105 reviews

Seasons at Mount Snow 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 WiFi upgrade to fiber optics 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

4.89 out of 5 average rating, 227 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.

4.91 out of 5 average rating, 164 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.

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, 243 reviews

Mt Snow Ski In/Out at Seasons

Directly on the mountain. Minutes walk to 2 trails. Full kitchen, dishwater, washer/dryer, microwave. Fireplace with free wood. Large screen TV in living room and tv in each bedroom. Plenty of board games. King size bed in Master. Free parking for 2 cars. Ground floor with deck with tables and chairs for relaxing. Free parking. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.

4.97 out of 5 average rating, 359 reviews

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

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!

4.84 out of 5 average rating, 381 reviews

Cabin in Woodford

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.

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

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

4.81 out of 5 average rating, 85 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.

4.9 out of 5 average rating, 20 reviews

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.

Home in Dover

Private chalet | hot tub, shuttle & ski home trail

4.96 out of 5 average rating, 23 reviews

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

Condo on the mountain

5 out of 5 average rating, 35 reviews

Home in Wilmington

Rustic home near skiing & lakes, walk to downtown

4.73 out of 5 average rating, 80 reviews

Home in Wardsboro

5.2milesSkiing/CozyCabin:HotTub/Mount Snow

4.92 out of 5 average rating, 85 reviews

Home in Dover

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

4.95 out of 5 average rating, 20 reviews

The kitchen features a central island with seating for eight, surrounded by wood cabinetry and modern appliances. Natural light filters through the large windows, highlighting the sleek black countertop and hardwood floors, creating a functional and inviting space for meal preparation.

Home in Wilmington

Stylish Chimney Hill Home - Close to Mt. Snow!

4.93 out of 5 average rating, 70 reviews

A historic red farmhouse and adjacent barn are set against a clear blue sky, surrounded by lush green grass. Stone pathways lead to the house, highlighting the inviting porch, while vibrant foliage borders the property.

Home in Whitingham

The Amos Brown House.

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

Home in Ancramdale

4.8 out of 5 average rating, 10 reviews

Family-Friendly Home on a Private Lake

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

5 out of 5 average rating, 5 reviews

The multi-story building features a light-colored façade and a central entrance with a green awning. Surrounded by greenery and gentle hills, the setting showcases a blend of natural beauty and well-maintained landscaping.

Apartment in Hancock

Ski-in/out condo

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.

The historic home is partially obscured by lush greenery, set against a blue sky with scattered clouds. A manicured lawn leads up to the house, which features a blend of classic architecture and modern elements visible through large windows.

Home in Troy

4.76 out of 5 average rating, 131 reviews

Riverfront Rustic 1824 Mansion

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

4.61 out of 5 average rating, 155 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

4.93 out of 5 average rating, 29 reviews

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

Ski-in/ski-out condo rentals

4.95 out of 5 average rating, 62 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 highlighted by a stone fireplace, featuring firewood neatly stacked beside it. A flat-screen TV is mounted above the mantel, with built-in cabinets on either side. A sectional sofa and wooden coffee table provide comfortable seating for relaxation.

5 out of 5 average rating, 24 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

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, 88 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.

4.96 out of 5 average rating, 48 reviews

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

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.

4.93 out of 5 average rating, 76 reviews

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

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, 65 reviews

Four Seasons Slope-side Getaway at Mount Snow

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.

4.94 out of 5 average rating, 49 reviews

Cozy Condo-4 Minute Walk to Skiing at Mount Snow!