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

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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 private hot tub is illuminated with soft blue lights, creating a relaxing atmosphere. The hot tub features multiple jets and is surrounded by wooden walls and a partially covered area, ensuring privacy. Warm ambient lighting enhances the tranquil setting, inviting relaxation.

Chalet in Killington

4.84 out of 5 average rating, 252 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

The Killington Chalet is your ideal vacation rental in the Green Mountains. It's the Right side of a duplex, perfect for families, couples, and groups. Located just off Killington Rd, it offers a secluded retreat near slopes, restaurants, and outdoor activities. Enjoy skiing, boarding, mountain biking, and more. Features include hot tub, sauna, boot dryer, wood stove, fire pit, and a fully equipped kitchen. Fresh linens, towels, and toiletries provided. Book for a memorable stay in every season!

Superhost

A cozy living area is presented, featuring a blue sectional sofa complemented by decorative pillows. A wooden coffee table sits in front, with remote controls arranged on top. Vintage skis are mounted on the wall, adding a rustic charm, while lamps provide soft lighting.

Apartment in Killington

4.84 out of 5 average rating, 274 reviews

Comfy ski in/out studio at base of Pico-Killington

Studio at the base of Pico with a balcony. Free shuttle service from my place to Killington, which is 10 minutes away.Brand new sofa bed with a pillow top. Room divider. Lots of TV channels with Xfinity. Luggage cart and elevator for easy access. Fast Wi-Fi. Free ski locker with one key for each guest. There is a laundry room with coin operated machines. The kitchen is fully equipped. Towels, soap, shampoo and conditioner provided for one day. No daily cleaning service. No parties. Free parking

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, 158 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

The living area features a plaid sofa paired with a wooden coffee table. A dining space with wooden chairs is positioned nearby. Accents include a unique ski decoration on the wall and window coverings that provide privacy while allowing natural light.

Apartment in Killington

4.89 out of 5 average rating, 149 reviews

Cozy One-Bedroom Ski Home Condo

Ski Home to Trail Creek Close to the mountain Updated 1-level, 1 bed, 1 bth, condo has brand new stainless appliances. Walking distance to Snowshed Base where you can access skiing, biking and the "fun" center. Ski home from Snowshed Slope trail. Steps to the amenities building that houses the pool, hot tub, sauna & exercise area. Wood-burning fireplace, free firewood, in-unit laundry. The view outside is of bucolic woods and a small stream. Killington will not run the shuttle mid-week.

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, 191 reviews

CozyCub - Pool, Hiking, Mountain Biking

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.

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, 152 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.

Superhost

A modern living area is presented with a cozy sofa and decorative throw pillows. A sleek wall-mounted TV rests above a rustic fireplace, with a stylish media console below. Light wood accents and a geometric patterned rug contribute to the inviting decor centered around comfort and relaxation.

Apartment in Killington

4.92 out of 5 average rating, 178 reviews

Renovated unit, prime location! Shuttle on/Ski off

We are located in Killington, VT. A newly renovated family friendly condo complex located on East Mountain Rd. Take the free shuttle (modified schedule post Covid) and end your day by skiing back to the condo. In the summer season you can enjoy a day mountain biking and ride home in just under five minutes. Enjoy the outdoor pool during the summer after a day of mountain biking! Year round activities all within a short distance.

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, 123 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!