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, 266 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 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.

4.98 out of 5 average rating, 50 reviews

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

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.

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.

4.87 out of 5 average rating, 124 reviews

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!

4.92 out of 5 average rating, 120 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, 101 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, 177 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 !

5 out of 5 average rating, 139 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

Forest Chalet Near Herbal Gardens

Relax in a quiet forest 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.

4.92 out of 5 average rating, 106 reviews

MountSnow ski on/off condo in Vermont

Ski seasons just began 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

4.9 out of 5 average rating, 230 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, 168 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, 249 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.

Popular amenities for Lanesborough ski-in/out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/out house rentals

4.82 out of 5 average rating, 87 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.

4.88 out of 5 average rating, 26 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

4.31 out of 5 average rating, 13 reviews

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.

Home in Hancock

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

5 out of 5 average rating, 41 reviews

Large Game Room, near skiing, walk to downtown

4.78 out of 5 average rating, 140 reviews

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

Riverfront Rustic 1824 Mansion

4.92 out of 5 average rating, 86 reviews

Home in Dover

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

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.

4.89 out of 5 average rating, 28 reviews

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

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.

4.91 out of 5 average rating, 23 reviews

Stylish Chimney Hill Home - Close to Mt. Snow!

Family-friendly, ski-in/out home rentals

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.

Flat in Hancock

4.83 out of 5 average rating, 41 reviews

Mountainside Condo Ski on/off

5 out of 5 average rating, 5 reviews

A row of townhouses is set against a clear blue sky, with snow blanketing the ground. Multiple chimneys rise from the rooftops, and balconies are visible on each unit, providing outdoor space for enjoyment. Surrounding trees add a natural element to the scene.

Home in Dover

Mt Snow Townhouse - Ski On/Off

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.

4.82 out of 5 average rating, 38 reviews

Unique - Country suite @ Jiminy Peak

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, 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

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.

4.61 out of 5 average rating, 158 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

4.94 out of 5 average rating, 31 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

4.84 out of 5 average rating, 195 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

Ski-in/out apartment rentals

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, 63 reviews

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, 89 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.

4.94 out of 5 average rating, 53 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.

4.94 out of 5 average rating, 82 reviews

Ski in-out Seasons Condo on mtn-sports 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, 71 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.

4.95 out of 5 average rating, 59 reviews

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

A cozy living area features a mix of orange and brown sofas, complemented by a wooden coffee table. A stone fireplace is positioned beneath a wooden panel wall, with a television mounted nearby. Large windows illuminate the space, offering views of the snowy outdoors.

4.83 out of 5 average rating, 18 reviews

Mount Snow direct access! Pool & hot tub! Ski

A living room features a wood-burning fireplace with an exposed brick surround, accompanied by neatly stacked firewood. A large flat-screen television is mounted above the mantle. Natural light enters through sliding glass doors, which lead to an outdoor seating area.