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

4.89 out of 5 average rating, 234 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.

4.94 out of 5 average rating, 109 reviews

Condo in Rutland

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.

4.92 out of 5 average rating, 156 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.

4.84 out of 5 average rating, 131 reviews

Okemo Clock Tower Base Ski-in/Ski-out Condo

Large family friendly 1-bedroom condo with 1 King and 1 Sofa bed that is just steps away from Okemo Base lodge. Please note there is no AC at this condo complex summer time, fan will be provided. - Dedicated Xfinity modem and AP in the unit. Video conference friendly. - Free parking - Coin operated washer/dryer facilities in the building - Super quite neighborhood during Summer/Fall season, and Ski in and out in Winter season. Fireplace has been updated to electric fireplace.

4.78 out of 5 average rating, 193 reviews

Okemo Mountain Getaway for Families w/ Pool Access

Perched on Okemo mountain, this spacious condo is the perfect year-round escape for families and groups. With ski-in/ski-out access, a cozy wood-burning fireplace, and a private balcony, it's perfect for any season—whether you're carving the slopes, hiking scenic trails, or enjoying the vibrant fall colors. Take a dip in the seasonal shared pool or unwind in the hot tub. Featuring a fully equipped kitchen, BBQ grill, and all the comforts of home, it's the ideal mountain getaway!

4.81 out of 5 average rating, 154 reviews

Charming 3 Bedroom 2 Bath 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, convenience doesn’t get any better. 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.

4.87 out of 5 average rating, 249 reviews

Chalet in Killington

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.

4.96 out of 5 average rating, 137 reviews

Dog-Friendly Mtn Escape/AC/Pool/

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 electric 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!

4.93 out of 5 average rating, 172 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.

4.95 out of 5 average rating, 100 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.

4.97 out of 5 average rating, 117 reviews

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!