Ski-in/Ski-out holiday rentals in Rutland County

Find and book unique ski-in/out homes on Airbnb

Top-rated ski-in/out rentals in Rutland County

Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

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Guest favourite

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.

Apartment in Killington

4.87 out of 5 average rating, 245 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.

Top guest favourite

A balcony is featured with a round glass table and two metal chairs, overlooking a vast mountainous landscape. Ski equipment stands against the wall, while natural light highlights the warm tones of the balcony's siding.

Apartment in Rutland

4.95 out of 5 average rating, 112 reviews

Ski on Ski off killington/ Pico mountain condo

Beautiful ski on ski off condo at the foot off Pico mountain ski resort. Free shuttle bus to Killington and Rutland at front door. 4th floor (top floor) condo with elevator. Balcony with view of Dears Leep overlook. Quiet top floor end unit. Full kitchen, 1 bedroom with seperate living room. Living room has pull out sofa bed and 54 inch t.v. and WIFI. Hike the Appalachian, Long and Catamount trails from your back door. 30 minutes from Woodstock. Please be sure to read and agree to house rules.

Guest favourite

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.

Apartment in Ludlow

4.92 out of 5 average rating, 159 reviews

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 wood-burning 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.

Guest favourite

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.

Apartment in Killington

4.93 out of 5 average rating, 192 reviews

CozyCub- Location, Fireplace, 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, settle in by the gas fireplace, or head out to explore.

Guest favourite

A spacious living area features a large stone fireplace with a flat-screen television mounted above. Comfortable seating is arranged around a wooden coffee table, creating an inviting space. In the background, the kitchen and dining area are visible, offering a seamless connection to the living space.

Apartment in Killington

4.95 out of 5 average rating, 105 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

Ski On-Ski Off!! Beautiful remodeled condo is in the heart of Sunrise at Bear Mountain. The designer kitchen features granite counter tops and top of the line stainless steel appliances. The main focal point in the living room is a massive stacked stone fireplace with a flat screen on the mantel. Recent upgrades include new living room furniture, master bed room furniture & updated tile in both showers. Additionally I own the adjoining unit & if you want more info see below

Superhost

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

4.84 out of 5 average rating, 104 reviews

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

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!

Top guest favourite

A spacious living area features large windows allowing natural light to fill the room. A comfortable sectional sofa is arranged around a coffee table, and a TV is positioned near a wood-burning fireplace. A decorative artwork of a bull's head adorns the wall.

Apartment in Killington

4.97 out of 5 average rating, 153 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

Contactless checkin steps from Killington Skiing/ Mountain Biking/ Adventure Center, refurbished ski-home condo with its own private sauna, hotel-style condo amenities, excellent common area (pool, jacuzzi, showers, etc) in idyllic central Vermont. Travel guide provided after booking! The resort includes an indoor pool, two hot tubs, pool table, treadmills, and is nestled at the base of the mountain with its own ski-home trail (or mountain bike-home in the summer).

Guest favourite

A warm living space is crafted with wooden paneling and large windows that provide natural light. Comfortable seating includes a leather sofa and patterned armchairs, arranged around a wooden coffee table. Soft lighting is provided by lamps, enhancing the cozy atmosphere.

Chalet in Killington

4.87 out of 5 average rating, 252 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

Short walk (200 yds) to Homestretch ski trail at Killington ski mountain. Trail is weather dependent, from late Dec to mid-March. If the nearby trail is not open, it will not be available. Close to hiking/biking trails, golf, nightlife, rivers and lakes. Large open living space and lots of sleeping space makes our home comfortable for large groups. Driveway holds up to 5 cars. Enjoy relaxing in the hot tub, sauna or spending time by the fire.

Guest favourite

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.

Apartment in Ludlow

4.92 out of 5 average rating, 148 reviews

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.

Guest favourite

The living area features a cozy fireplace surrounded by stone, with a wooden mantel. A dining table with white chairs is positioned near the kitchen, complemented by bar stools at the counter. Light floods in through large windows, enhancing the open layout.

Apartment in Ludlow

4.95 out of 5 average rating, 103 reviews

Winterplace - Steps away from Slopes

Newly updated condo at Winterplace Okemo. This sunny corner 3 bedroom unit is just steps to the top of the A-B Quad. Completely renovated from floors to ceiling The delightful fireplace place will keep you toasty in the cozy living area. Outdoor ski locker just outside back door. Front door parking, and firewood included. Pool is open and available to renters all year. Hot tub in winter months and tennis courts in summer.

Top guest favourite

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.

Apartment in Killington

4.96 out of 5 average rating, 151 reviews

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

Experience year-round adventure at Sunrise Village at Killington, just steps from scenic trails and the Sunrise Village Triple Lift (488 ft away). After a day of outdoor fun, unwind by the cozy gas fireplace. Explore nearby hiking, mountain biking, kayaking, and golfing. The indoor sports complex—featuring a pool, hot tub, and gym—is a short walk away. Perfect for outdoor lovers looking to relax and make unforgettable memories!

Guest favourite

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

4.96 out of 5 average rating, 125 reviews

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!