Ski-in/Ski-out holiday rentals in Mount Holly

A cozy living space features a large window providing natural light. A comfortable couch and chair are positioned around a coffee table. The room includes a spacious bed with a blue and black patterned blanket, while a 50-inch TV is mounted on the wall.

4.88 out of 5 average rating, 259 reviews

Killington-Pico ski in/out Studio at base of Pico

At the base of Pico and 10 minutes from Killington. Free shuttle service from my place to Killington. I have a free ski locker and free wood for the fireplace. There is a laundry room with coin operated machines. There is a brand new 50” flat screen tv with cable. It’s a smart tv, that’s hooked up to WiFi, so you can use your Netflix, Amazon or Hulu account if you want. The kitchen is fully equipped. Towels, soap, shampoo and conditioner provided for 1 day. No daily cleaning service. No parties.

A living room with a gas fireplace built into a brick facade provides warmth. A comfortable sectional couch faces the fireplace, complemented by a small coffee table. Large sliding glass doors open to a balcony, offering views of greenery outside.

4.98 out of 5 average rating, 153 reviews

Cozy Mountain Condo

Updated 1 Bdr Whiffletree condo in the heart of Killington minutes from everything. The condo is fully stocked with all of the essentials you will need for your Vermont get away. Ski locker for all your gear! Sleeps up to 4 with a king bed and queen pullout sofa. Baby Pack & Play crib, mattress and sheets available upon request for $50 per stay. Shuttle in/out service available weekends (Dec–April), or ski home when conditions allow (check Killington trail status). Killington Reg #004858

A spacious living area features comfortable seating on a plush sofa and armchairs. A round wooden coffee table is positioned centrally, alongside a dining table with multiple wooden chairs. Natural light fills the space through large windows, enhancing the cozy atmosphere.

4.81 out of 5 average rating, 167 reviews

Free Shuttle Route-Charming 3 BR 2 BA Ski Home/Off

Looking to enjoy all that Killington has to offer in just minutes? Ski home access, a prime location on the shuttle route, and just a 2-minute drive to the slopes. Super convenient! This newly refreshed three-bedroom, two-bathroom condo offers modern comfort and a cozy vibe. After a day of outdoor fun, kick back on the plush sofa and unwind by the warmth of the gas fireplace. It's the ultimate retreat to recharge and enjoy the beauty of Vermont. SHUTTLE OPERATES FRIDAY-SUNDAY & HOLIDAY WEEKS

4.92 out of 5 average rating, 112 reviews

The spacious great room features a wood-burning fireplace and is furnished with two comfortable sofas and a wooden coffee table. A large flat-screen TV hangs on the wall, and natural light emanates from the surrounding windows. A dining area with a circular table is visible in the background.

Home in Ludlow

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

PLEASE NOTE: No Saturday arrivals or departures, no pets, no parties Recommended local activities & floor plans of our home can be found on our OkemoHouse site Our "Trailside Chalet" is ON OKEMO MOUNTAIN, a 200 yard walk downhill from the Sunshine Chairlift & Suncatcher ski trail on Okemo's Southface (open end if Dec - late Mar). This Classic Vermont Ski Chalet features 5 bedrooms, sleeps 12, and is on a private wooded lot overlooking a babbling brook with seasonal fire-pit & charcoal grill.

4.92 out of 5 average rating, 172 reviews

An open-concept living area is seen, featuring a fully equipped kitchen with a breakfast bar. Warm wood accents and cozy seating are highlighted, while a decorative sign with a ski theme adds character to the space. Natural light filters in through large windows.

Condo in Ludlow

All Season Lovely and Zen Okemo Mt Lodge Condo

Tired of city life and want a fresh breath? Feel the call from nature while also desiring some sporty fun? Come enjoy our lovely and Zen Condo right at the foot of beautiful Okemo! True ski-in/ski-out in the winter. Enjoy your warm ski day lunch by sitting next to the fireplace, while watching all the activities on the slope. In the warm weather, enjoy the beautiful hiking trails and golf course that Okemo offers, as well as water activities at the nearby lakes and rivers.

4.85 out of 5 average rating, 110 reviews

The exterior of a contemporary timber home is visible, featuring a sloped green metal roof and warm wood siding. Surrounding snow-covered ground reflects nearby evergreen trees. The property is situated on a spacious lot, offering a serene winter landscape.

Townhouse in Killington

SKI ON/OFF Spruce Glen C | Sauna| Fireplace | AC

Come and enjoy the largest private trailside property in Killington (almost 4 acres), with more convenience and value than large house rentals and more privacy than condo villages. The direct ski on/off is the easiest you'll find in Killington. Quiet and serene, the mature New England Evergreens and gentle mountain stream are a tranquil relief. An ideal ski in ski out or any season vacation getaway. Great Eastern is the longest green run in the East. Welcome to Spruce Glen!

A modern kitchen with a circular dining table surrounded by four wooden chairs is featured. Stainless steel appliances, including a microwave and oven, are present. A stylish light fixture hangs above the table, while the fireplace and sports equipment are visible in the background.

4.92 out of 5 average rating, 205 reviews

Cozy 1BR, Shuttle/Walk to Lifts, Covered Parking

Our bright and cozy 1-bedroom condo in Building 3 at Mountain Green Resort is the perfect home base for your Killington getaway. Reserved parking spot in the garage. Walk to Snowshed Base Lodge or hop on the winter shuttle that runs every 15 minutes. Enjoy a renovated kitchen, dedicated Wi-Fi, and smart TVs for easy streaming. Resort amenities include an indoor pool, hot tub, sauna, and gym year-round, plus an outdoor pool from Memorial Day through mid-September.

4.9 out of 5 average rating, 115 reviews

A comfortable living area features a wood fireplace with tools nearby and a mounted television above it. Two armchairs flank a rustic coffee table, creating a cozy space. Large windows allow natural light to fill the room while offering views of the snowy outdoors.

Home in Killington

Trail Creek - ski home!

Enjoy Killington at competitive pricing without sacrificing comfort! Located in Trail Creek Condo Association. • Ski, hike, bike, or golf just steps away • Cozy up by the wood fireplace (free wood) • Pool, hot tubs, sauna, and game room at community center • 6-minute walk to Snowshed or shuttle (winter weekends/holidays) • Ski home trail (snow-dependent) • Minutes to restaurants, bars, and shops • Convenient bus stop Adventure and relaxation await!

4.93 out of 5 average rating, 167 reviews

A view of the snow-covered path leading to the ski slopes is framed by the C Building’s balconies. Sunlight casts long shadows across the pristine snow, highlighting the tranquil winter scene. The surrounding area is clear and inviting, with ski signage visible in the distance.

Condo in Ludlow

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

A cozy living area is visible, featuring a dining table surrounded by bright yellow chairs. A fireplace is seen, enhancing the space, while a large bear-themed wall mural adds a touch of nature. Natural light floods in from the nearby window.

4.93 out of 5 average rating, 206 reviews

CozyCub- Location, Ski Off/Shuttle On!

Delight in this friendly, fully renovated (2022) modern ski condo next to Killington's popular Snowshed base area, learn-to-ski trails, and golf course. Shuttle-On / Ski-Off to the condo during peak season. The location is prime for accessing everything the area has to offer. Relax for some streaming after a day on the mountain on the 65" TV. Enjoy the Whiffletree condo association's outdoor pool and tennis courts in the summer.

4.96 out of 5 average rating, 136 reviews

A cozy living area features a brick fireplace with a warm fire. A comfortable sofa adorned with decorative pillows is positioned nearby, accompanied by a wooden coffee table. Wall-mounted art and soft lighting enhance the welcoming ambiance.

Townhouse in Killington

Beautiful Spacious Condo at Killington Resort

This cozy and spacious Sunrise Mountain Village condo is perfectly situated to nearby mountain sports at Killington Ski Resort. It welcomes up to eight guests for an unforgettable stay in the Green Mountains! Exceptional access to year round outdoor activities, great community amenities, and a comfortable condo to come home to - what more could you ask for? Book Timberline K4 today for a thrilling Vermont getaway!

A cozy living area features a brick fireplace at its center, surrounded by two comfortable armchairs and a wooden coffee table. A Roku Smart TV is positioned next to large glass doors leading to the balcony, while a mirror reflects the warm ambiance. Natural light enhances the wooden accents on the walls.

4.84 out of 5 average rating, 168 reviews

Cozy Condo- Close to Mountain, Ski home trail

Experience Killington like never before with our ski-home condo and a free 5min shuttle ride to the mountain on winter weekends. Our home is the perfect location to experience all that Killington has to offer. It has a free shuttle and a ski home trail. As well as quick and convenient access to Killington's great nightlife including restaurants, shopping, bars, and entertainment.

Popular amenities for Mount Holly ski-in/ski-out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

4.78 out of 5 average rating, 23 reviews

Home in Killington

The Navillus House: Hot Tub, Slopeside, Ski On/Off

4.76 out of 5 average rating, 29 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

4.93 out of 5 average rating, 30 reviews

A cozy living area features a stone fireplace with a warm fire, surrounded by a modern sofa. Above the fireplace, a wall-mounted television is visible. A rustic chandelier with multiple bulbs hangs over a dining table, while decorative items are placed on a nearby side table.

Home in Ludlow

Ski-In/Ski-Out Hike Okemo Condo Solitude Village

5 out of 5 average rating, 5 reviews

A spacious outdoor deck is visible, supported by a solid structure. Two comfortable chairs are arranged on the deck, providing a place to relax. The surrounding lawn is well-maintained, and vibrant foliage can be seen nearby, indicating the changing seasons.

Home in Ludlow

Okemo Condo – Ski In/Out

4.95 out of 5 average rating, 19 reviews

A sweeping aerial view captures the surrounding mountain landscape, showcasing the well-groomed ski trails stretching across the slopes. The townhouse property is situated at the base, marked clearly, among a collection of neighboring homes set amidst the snowy terrain.

Home in Killington

Topridge Ski-on/Ski-off | 4BR w Game Room!

4.95 out of 5 average rating, 168 reviews

A cozy fire pit is surrounded by stone, situated in the foreground of a spacious lawn. In the background, a modern chalet features large windows and a combination of wood and stone siding, framed by colorful autumn foliage.

Home in Winhall

Summit View Ski and Golf Retreat w/hot tub & Sauna

5 out of 5 average rating, 29 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

4.93 out of 5 average rating, 95 reviews

Home in Dover

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

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

4.98 out of 5 average rating, 81 reviews

A circular outdoor pool is surrounded by a landscaped area, featuring several trees and bushes. The building's large glass entrances reflect natural light. Sun loungers are positioned nearby, and a set of steps leads from the pool to the patio area.

Condo in Stratton

Stratton Long Trail House: Quick Walk to Lifts!

4.97 out of 5 average rating, 223 reviews

A charming cabin constructed from natural materials is nestled among lush trees in a forested area. Sunlight filters through the leaves, casting dappled shadows on the ground. The cabin features large windows that invite the surrounding greenery inside.

Tiny home in Hartland

Cabin on the Hill

4.95 out of 5 average rating, 120 reviews

The view from the deck showcases the snowy slopes bustling with skiers and snowboarders. The nearby ski lift is visible, alongside several groups engaging with equipment. In the background, a multi-story building is situated among the trees, contrasting against the winter landscape.

Condo in Ludlow

Slopeside condo at the base of Okemo-steps to lift

A cozy living room features a dark leather sofa adorned with decorative pillows. Above the couch, three framed nature-themed art pieces display serene mountain landscapes. A dog rests comfortably on the carpet, with soft lighting from two side lamps enhancing the peaceful ambiance.

4.94 out of 5 average rating, 163 reviews

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

4.96 out of 5 average rating, 77 reviews

Perfect 2 Bedroom Ski in/out at Killington

A spacious living area is highlighted by a comfortable gray sofa and a wooden coffee table. Natural light streams through large windows, complementing the warm wood paneling that separates the sleeping nook. A flat-screen TV and a cozy seating arrangement add to the inviting ambiance.

5 out of 5 average rating, 28 reviews

Cozy Slopeside Studio at Pico

5 out of 5 average rating, 55 reviews

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.

Condo in Stratton

Your Vermondo awaits: Steps to Lifts & Village.

4.98 out of 5 average rating, 57 reviews

A spacious living area features a leather sectional sofa and a dining table with black chairs. Soft lighting is provided by pendant lamps overhead. A TV is positioned next to the kitchen, which is visible in the background, enhancing the open layout of the space.

Townhouse in Ludlow

Ski-In/Out Condo Okemo Trailside On The Mountain!

Ski-in/ski-out cabin rentals

4.76 out of 5 average rating, 25 reviews

A spacious cabin is viewable from above, surrounded by vibrant autumn foliage. A large wooden deck features patio furniture, including a red umbrella and seating area. Decorative stone walls and gravel pathways enhance the natural setting, with a tree-lined road curving nearby.

Cabin in Killington

Killington Golf&Mtn Biking. Hot tub & Fireplace!

4.76 out of 5 average rating, 425 reviews

A spacious interior showcases warm wooden floors and a cozy wood-burning stove at the center. Soft lighting from multiple pendant lamps creates a welcoming ambiance. A dining area with a wooden table and chairs is visible, and rustic details can be seen in the surrounding decor.

Cabin in Londonderry

Beautiful Art Studio with hot tub/sauna #1 Airbnb

4.85 out of 5 average rating, 252 reviews

A spacious log cabin is set amidst lush greenery, featuring a welcoming porch and multiple windows that allow natural light to fill the interior. The well-maintained lawn offers a peaceful atmosphere, with trees surrounding the property, enhancing the sense of seclusion.

Cabin in Mendon

THE CABIN....a Vermont log home

4.68 out of 5 average rating, 456 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

4.88 out of 5 average rating, 89 reviews

The exterior of the chalet is highlighted by a warm wooden facade and an inviting staircase leading to the entrance. Snow blankets the ground and roof, with seasonal decorations adorning the front. Tall trees surround the property, creating a serene winter atmosphere.

Cabin in Londonderry

Magic Mt Getaway - Close to Bromley Stratton Okemo

4.95 out of 5 average rating, 100 reviews

A cozy cabin with a crisp wooden exterior is located amidst lush greenery and trees. A serene pond is visible nearby, with a flower farm and several outbuildings in the background. Expansive fields lead towards the picturesque landscape of mountains under a cloudy sky.

Cabin in Bethel

The Gourmet Cabin at Stitchdown Farm

4.96 out of 5 average rating, 220 reviews

A cozy log cabin is framed by snow-covered trees, showcasing a steep, metal roof and rustic wooden exterior. The porch features wooden pillars and a welcoming entrance, creating a serene setting in the winter landscape.

Cabin in South Royalton

Cozy 4-season Cabin on Pond - "East Cabin"