Ski-in/Ski-out holiday rentals in The Berkshires

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

Top-rated ski-in/out rentals in The Berkshires

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Guest favourite

Apartment in Dover

4.95 out of 5 average rating, 58 reviews

Condo w/ great amenities 4-seasons! Ski in Ski out

True ski in ski out ground floor condo w/ private entrance. Wood burning fireplace, wood included! King size bed in master, true Queen murphy bed, 1-memory foam cot, plus air mattress. Fully stocked & functional kitchen, including Keurig & Mr. coffee. Full bath w/blow dryer. Seating; kitchen counter, expandable table, wine barrel bar top. Walk out the door & down the steps to the NEW Sundance high speed lift. Take the Seasons trail home. Brand new state of the art Sports Center included.

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Apartment in Dover

4.82 out of 5 average rating, 11 reviews

Mt. Snow Ski in/Ski out condo/tennis/pickle courts

2 bedroom ski in/ski out condominium. Full kitchen, large screen TV's, cable, wifi, and fireplace. Literally ski onto and off your private deck on this quiet ground floor walkout. When your done skiing enjoy a Full amenities center with a kids play area, x-box, swimming pool, hot tubs, and 24 hour gym access. Kitchen has coffee maker, garbage disposal, granite countertops. 2 Bathrooms. Master bedroom-King bed Second Bedroom-bunk bed (Twin over Full). Pullout couch with comfortable mattress.

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Apartment in Londonderry

4.93 out of 5 average rating, 29 reviews

Magic Mountain Trailside Condo Ski In / Ski Out

This Property is a 1 BR, Trailside Condo with Ski In / Ski Out Trail Access. 1 of 2 units with a private entrance and no units above or below. The layout includes 1 BR, 1 BA, open kitchen, living/ dining room. The sliding glass doors in the living room leads to a private deck and access to the mountain trails. Take advantage of this year round getaway location with mountain views, hiking, ski/ snowboarding, golf, disc golf, fishing, SUP, kayaking, live entertainment, shopping and dining.

Guest favourite

Home in Killington

5 out of 5 average rating, 14 reviews

Sunrise B2- ski on and off, hot tub, pool

Sunrise Resort Condo, Killington, VT: Slope-side Luxury Immerse in breathtaking views at this ski on/ski off condo near Bear Mountain's trail. This 4BR, 3BA sanctuary sleeps 8 with three queen rooms, a bunk, and pull-out. Enjoy HD Roku TV, a walkout patio, fully-equipped kitchen, and in-home laundry. Resort perks: nearby ski lift, seasonal pools, hot tubs, gym, sports courts (tennis, pickleball, basketball), hiking, skiing trails, and an inviting cafe. Dive into Killington's best. Book now!

Guest favourite

Apartment in Killington

4.9 out of 5 average rating, 68 reviews

1BR Ski-Home Pool/HotTb, Walk 2 Lifts, golf

Adventure Awaits! ⛷ Killington Vermont, the “Beast of the East” is a 4 seasons resort of astounding natural beauty. Whether conquering moguls, on Mountain biking, golfing or sipping hot cocoa by the fire, Killington has something for everyone. This ground floor, SKI-HOME 1 BR Condo at Trail Creek comfortably sleeps 4. Enjoy the indoor pool/hot tub/sauna at Trail Creek’s shared amenities center. Free parking/High Speed WiFi/Cable/Firewood. Fully stocked kitchen. 50” HD Roku TV.

Guest favourite

Apartment in Dover

4.8 out of 5 average rating, 71 reviews

Mt Snow - Steps away from slopes

Directly on the mountain. Ski right back to your door. Less than 2 minute walk to the trails. Full kitchen, dishwater, washer/dryer, microwave. Fireplace with free wood. Large screen TV in living room and 1 in master bedroom. Ground floor with a private deck for relaxing. Ample parking. Condo across the hall is also available for larger groups. The pool (indoor and outdoor) and hot tubs are open and available to renters as is fully equipped gym (all year) and tennis courts in summer.

Guest favourite

Apartment in Stratton

4.94 out of 5 average rating, 170 reviews

Updated Ski in/Ski out Stratton Condo!

Enjoy our cozy ski-in ski -out condo in the Ober Tal complex at Stratton. This newly renovated condo offers a warm, welcoming stay with modern farm house charm! Located just above the base of the mountain, our condo is a stones throw from the nearest lift ( 200 ft) and a ski lovers dream. Unwind after a long day of skiing/snowboarding or take convenient 5 minute stroll to the Village for a bite to eat or some shopping. *Mountain biking & concerts offered in the summer season.*

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Apartment in Ludlow

4.84 out of 5 average rating, 130 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.

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Apartment in Ludlow

4.8 out of 5 average rating, 185 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!

Guest favourite

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

Top guest favourite

Apartment in Vernon Township

4.94 out of 5 average rating, 145 reviews

Ski-In/Ski-Out @ Mountain Creek-Pool/Hot Tub/Sauna

NEWLY Renovated! Top floor 1 bedroom Condo with Mountain/Pool View at Mountain Creek Resort. Steps away from ski mountain & gondola ! Swim in the outdoor heated saltwater pool, relax in the sauna or soak in the hot tub while taking in mountain views, Catch the sunset from your private top floor balcony or cozy up by your gas fireplace. Visit award-winning spas, golf, breweries, wineries, farms, and fine dining at Crystal Springs & Warwick, NY--only 10 min away.

Guest favourite

Apartment in Killington

4.97 out of 5 average rating, 144 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).