Ski-in/Ski-out holiday rentals in Stratton

4.9 out of 5 average rating, 183 reviews

A spacious ski home is surrounded by snow-covered trees, featuring a modern design with a sloped metal roof. Large windows allow natural light to enter, while a gravel driveway leads to the entrance. This bustling wooded area provides a serene backdrop during winter.

Home in Peru

Beautiful Bromley/Manchester VT Retreat w/hot tub

"Manchester Moose!" Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester, Beautifully remodeled VT vacation getaway nestled in the Green Mountains. Closest skiing to quaint Manchester VT, minutes from snowmobiling, hiking, fine dining and shopping. This home features 5 bedrooms, 3 with queen beds including 2 Masters, and 2 bedrooms with double bunks. Perfect for 2 or 3 families to enjoy any season in Southern Vermont's beautiful Green Mountains! YouTube video link @GreenMountainStay

4.85 out of 5 average rating, 144 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 Table 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 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, 105 reviews

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

⌲ Escape to Seasons on Mount Snow & stay in our fully equipped 3 bedroom condo where you can you can ski-in & out directly from the condo building! ⌲ Enjoy the log burning fire (wood provided), smart TV & boardgames plus the fabulous Seasons on Mount Snow facilities which include a gym, pool, hot tub, sauna & fire pit. ⌲ Spring thru fall activities in the area include hiking, biking, tennis & pickleball (at Seasons), scenic rides, lakes, golf, camp, spa & enjoying the stunning fall colors.

4.92 out of 5 average rating, 128 reviews

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

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, 107 reviews

Great Amenities-Season Condo gym-sport center-pool

True ski in ski out ground floor condo w/ private entrance. Wood burning fireplace, wood included! King size bed in master, true Queen murphy bed, 1-memory foam cot, plus air mattress. Fully stocked & functional kitchen, including Keurig & Mr. coffee. Full bath w/blow dryer. Seating; kitchen counter, expandable table, wine barrel bar top. Walk out the door & down the steps to the NEW Sundance high speed lift. Take the Seasons trail home. Brand new state of the art Sports Center included.

5.0 out of 5 average rating, 136 reviews

A mid-century modern home set among lush greenery features a stone foundation and large windows. A brick chimney rises above the roofline, while several wooden Adirondack chairs are positioned on a stone patio, providing a relaxing outdoor space to enjoy the surrounding nature.

Home in Cavendish

Midcentury Hillside Retreat - Summer Paradise

Enjoy this peaceful retreat in the heart of the Green Mtns and surrounded by 130+ acres of private woodland. Dramatic field stone fireplace and spectacular panoramic views of Mt Ascutney into New Hampshire from the entire living space. Large chef's kitchen. Private master suite and two guest bedrooms. The perfect get-away for relaxing with family and friends. Exceptional hiking, biking and Connecticut River adventures. Near GMHA and Woodstock. Great restaurants, fun village shopping nearby.

4.9 out of 5 average rating, 241 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 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.

5.0 out of 5 average rating, 17 reviews

Stratton walk on/off, walk to village, fireplace

This Obertal 1 bedroom 1 bathroom is PERFECT for your weekend and week long getaways to Stratton! After a long drive, park and unload your car and don't worry about her for the rest of your stay! With the mountain just steps away you can walk to skiing/riding, apres drinks, dinner, music, and shopping! • 1 bedroom (Queen) • 1 bathroom • 1 pullout sofa in the living room (Full/Queen) • Walk on/off skiing/riding • Walk to Village (food, drink, shops) • Fireplace

4.89 out of 5 average rating, 9 reviews

Walk to Ski Lifts & Village | Hot Tub & Sauna

Steps from Stratton Ski Lifts & Village --- This lovely 2BR/2BA condo with fireplace is perfect for a winter mountain escape. Park your car in the underground heated garage and hang up the keys for the rest of your trip—walk straight to the ski lifts and village shops and restaurants. The condo has a year-round outdoor pool, hot tubs, and sauna—ideal after a day on the slopes. Wonderful 2-level unit offers space to relax and unwind in the Vermont mountains.

An open living area features a large wooden dining table surrounded by metal chairs. The kitchen showcases modern appliances and a sleek countertop, while a comfortable seating area is arranged nearby with a sectional couch and coffee table against a textured wall.

4.97 out of 5 average rating, 120 reviews

Luxury Stratton condo just steps to the lift!

Enjoy this beautifully renovated 1 bed/1 bath condo with a live fireplace conveniently located steps from the mountain and Stratton Village! The Tamarack chair lift is only a few hundred yards away! Washer and dryer in unit to warm up your wet clothes after a long day of skiing or mountain biking. Fully stocked kitchen, 50’ TV w/ AppleTV, cable, Amazon Alexa, 5G WiFi, Firewood and more! This is one of the nicest Ober Tal condos available for rent!

4.93 out of 5 average rating, 113 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

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.

4.88 out of 5 average rating, 262 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. 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 Stratton ski-in/out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/out house rentals

4.96 out of 5 average rating, 133 reviews

Home in Dummerston

The Sugarhouse

4.88 out of 5 average rating, 154 reviews

A spacious open-plan living area features a large brown sofa alongside a comfortable leather recliner. Light blue walls are adorned with vintage ski decor. A coffee table sits centrally on a patterned rug, and a dining bar with seating overlooks the kitchen area equipped with modern amenities.

Home in Ludlow

1st floor, Okemo contemporary country 3 BR 2 BA

5.0 out of 5 average rating, 18 reviews

A cozy living area is illuminated by ambient lighting from a fireplace and table lamps. A television is mounted on the wall, while comfortable leather sofas face a wooden coffee table. Large windows reveal softly draped curtains and a gentle glow from a nearby table lamp.

Home in Stratton

Vintage Vermont

4.8 out of 5 average rating, 10 reviews

Home in Stratton

SnowBridge Stratton Ski in/Out Trailside 4 Bdrm

4.98 out of 5 average rating, 62 reviews

A charming front porch is displayed with seating arrangements that include a cozy sofa. The white exterior is complemented by wooden beams and decorative lights, while seasonal decorations, like corn stalks, add character. A vibrant landscape frames the home.

Home in Wilmington

Farmhouse With Large Game Room, Walk to Downtown

5.0 out of 5 average rating, 41 reviews

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

Modern Chalet: Magic Mountain

5.0 out of 5 average rating, 11 reviews

Home in Dover

Ski In/Ski Out Mount Snow Condo.

4.96 out of 5 average rating, 23 reviews

The living area features a stone fireplace as the focal point, complemented by large windows that allow natural light to fill the space. A sectional sofa provides ample seating, and a wooden coffee table anchors the room. A television is mounted above the fireplace.

Home in Dover

Seasons-walk to lifts, amenities clubhouse,hot tub

Family-friendly, ski-in/out home rentals

5.0 out of 5 average rating, 201 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

A spacious living area includes a large sectional sofa, a wooden dining table with chairs, and a flat-screen TV mounted above a fireplace. Natural light filters in through a large window, illuminating the soft beige walls and neutral carpeting.

4.91 out of 5 average rating, 32 reviews

Summit’s Stratton Sneak Away II

A cozy living area is illuminated by a gas fireplace, with a media console mounted above. A spacious sofa and wooden coffee table offer a comfortable seating arrangement. A bar-height dining area with stools is visible in the background, along with a work desk and ample natural light.

4.97 out of 5 average rating, 34 reviews

Renovated Long Trail 1 Bedroom

The living area features a spacious sectional sofa arranged around a coffee table, complemented by a cozy wood-burning fireplace. Natural light fills the room through large windows, which overlook the snowy landscape. A dining table for six and a media console housing a Smart TV are also present.

4.98 out of 5 average rating, 58 reviews

Ski In/Out, Cozy 3Bed condo steps to Village

A snow-covered landscape reveals nearby mountains and ski slopes under a clear blue sky. Trees with bare branches frame the scene, while quaint buildings and a parking area are visible in the foreground, suggesting a vibrant ski village atmosphere.

5.0 out of 5 average rating, 61 reviews

Your Vermondo awaits: Steps to Lifts & Village.

An aerial view showcases Ober Tal condo nestled among snowy landscapes, with the nearby Tamarack Lift visible along a snow-covered path. The surrounding area features trees and gently sloping hills, indicating a winter setting conducive to skiing and outdoor activities.

5.0 out of 5 average rating, 33 reviews

Walk to Lift - 2 Bedroom Condo - Newly Renovated

4.78 out of 5 average rating, 54 reviews

A modern kitchen is equipped with stainless steel appliances, including a refrigerator, oven, and microwave. White cabinetry contrasts with dark granite countertops, while a tile backsplash adds subtle texture. Warm wood flooring complements the overall design, creating a functional and inviting cooking space.

Townhouse in Stratton

Ski In / Ski Out 4BR / 3BA Private Hot Tub and sha

A scenic aerial view showcases the ski slopes in the background, bordered by a cluster of vibrant buildings in the foreground. The lively village is adorned with pathways and trees, emphasizing the proximity to shops and restaurants, inviting leisurely exploration.

4.93 out of 5 average rating, 75 reviews

Ski On/Off Condo in the Heart of Stratton Village!

Ski-in/out cabin rentals

4.83 out of 5 average rating, 120 reviews

Cabin in Peru

The Grateful Barn

4.88 out of 5 average rating, 104 reviews

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

Green Mt Magic - Close to Golfing Tennis Parks

4.94 out of 5 average rating, 182 reviews

The exterior of a red cabin is surrounded by a snowy landscape. Large windows allow natural light to illuminate the front space, while a simple wooden bench rests on the porch. Pine trees are visible in the background, creating a serene atmosphere.

Cabin in Cavendish

The Cozy Little Red Cabin

4.66 out of 5 average rating, 473 reviews

An inviting interior space features wood-paneled walls and ceiling. A cozy dining area with a round table and two chairs is seen, along with a pair of armchairs near a rustic wood stove. A ladder leads to a loft, while sunlight streams through multiple windows.

Cabin in Londonderry

The Run-In - Beautiful Country Cabin with Hot Tub