Ski-in/Ski-out holiday rentals in Canaan Valley

Big, Bright SLOPESIDE Ski Chalet, Outdoor Hot Tub!

Don't be fooled by other misleading "slopeside" listings! This gorgeous 5-bedroom lodge is adjacent to Timberline's Winterset ski run — perfect for families. Outdoor hot tub. Large open floor plan, plus separate living area downstairs. Two gas fireplaces. Master suite has Jacuzzi for 2. Wifi, 2 flatscreen HDTVs. Please don't request to book this chalet unless you have at least 3 positive reviews on Airbnb. If you don't have 3 positive reviews, your request to book will be respectfully declined

Newly Renovated Ski-In/Ski-Out House with Hot Tub!

Beautifully remodeled SKI-IN/SKI-OUT house with OUTDOOR HOT TUB right on Winterset ski trail at Timberline Mountain! Perfect for families, this spacious 4BR/3.5BA home is an ideal location to unwind and relax after a fun day experiencing the great outdoors, whether enjoying downhill or cross-country skiing, snow tubing, hiking, biking, swimming, fishing, golfing or exploring a state park, national forest or wildlife refuge! Come soak in all the splendor that wondrous Canaan Valley has to offer!!

Live It Up Lodge - Walk to Ski, Dog Friendly

Live It Up Lodge is a 3 minute walk to the slopes/biking/hiking, and tons of fun for the whole family! Ski season and year round, Live It Up Lodge is a convenient getaway for your family, sleeping 12 comfortably. Roast marshmallows by the fire, and challenge your friends to a variety of yard games like Cornhole, Jumbo Connect Four, Disc Golf, and more! Just a short drive to the cool mountain vibe of Davis & Thomas for music at the Purple Fiddle, a beer at Stumptown ales, and a gallery stroll.

Terrapin Station - Hot Tub - Year-round creek

Solar Powered, Luxury mountain getaway located within walking distance of Timberline Mountain Ski Resort. Large deck with gas fire pit overlooking year-round babbling brook. Vaulted ceilings showcase a stacked stone gas fireplace. 4 bedroom, 4 bath featuring 2 Main bedroom suites both with en-suite. Large open kitchen and dining area. Great gaming table for board games or cards. Leave your cares at the door and welcome to Terrapin Station in the heart of Wild and Wonderful Canaan Valley.

Dandy Flats - The Quaintrelle

Tucked inside the oldest historic buildings on the main drag in Thomas and adorned with 135-year old plaster walls, original woodwork, encaustic tile and purple marble - this tastefully styled flat is for those looking for the transportive experience historic buildings deliver. With espresso, galleries, live music, shops, food, and drinks steps away, you have the forests and a tiny cityscape just steps out your door. This apartment is offered at the Dandy Flats - a lovingly restored Inn.

Timberline Resort Condo - Walk to slopes

Welcome to Trees N' Skis, your charming retreat nestled just steps from the Timberline slopes and close to the scenic trails of Dolly Sods. This thoughtfully renovated 1-bedroom condo offers a perfect blend of modern comfort and rustic charm. Enjoy a cozy, well-appointed space designed for ultimate relaxation and convenience, whether you're hitting the slopes or exploring nearby trails. Experience the perfect mountain getaway, where every detail has been crafted with your comfort in mind.

Ski-in Ski-out directly on Winterset w/ Hot Tub

Escape to our cozy slopeside A-frame, steps from Winterset Trail at Timberline Mountain. Start your day with coffee by the fire, watching the groomers prep the slopes. Gear up in the boot room and hit the trail just seven steps away. After an epic day, unwind in the saltwater hot tub, challenge friends at the game table, and enjoy a movie in surround sound. With a fully equipped kitchen, space for everyone, and an onsite Tesla Universal EV charger, your perfect mountain getaway awaits.

Treeline at Timberline!

Walk to Dolly Sods!! Our spacious 2 bed, 2 bath has the best location. There are lots of hiking and biking trails easily accessible. The Wilderness Area, aka Dolly Sods is close by, or try out any of the other hikes. We have a pull out sofa bed for extra guests, a grill for BBQing on the balcony, and cozy gas fireplace that makes our condo hands down the best! When you tire from the hiking, biking or fishing, retire in style. Put you feet up and relax. And yes, we have wifi.

Cozy Cabin Jus Ta Ski Dream-at Timberline Mountain

Your family will be close to everything when you stay at this cozy, centrally-located cabin in the heart of Canaan Valley. Located just 400 feet from the 6 pack high speed lift at Timberline Moutain and 700 feet from the Timberline Mountain Lodge. Private parking(flat and does not require chains or 4 wheel drive) for your stay and a nice hot tub for relaxing after a long day of hiking, biking or skiing. 3 bedrooms, 2 full baths and comfortable sleeping arrangements for 9 people.