Ski-in/Ski-out vacation rentals in Windham County

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

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

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

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Guest favorite

Condo in Dover

5 out of 5 average rating, 51 reviews

Four Seasons Slope-side Getaway at Mount Snow

Come stay at our lovely slopeside condominium at seasons of Mount Snow where you’ll be staying in spacious one bedroom unit with a comfortable king size bed and a wonderful pull out couch that comfortably sleeps 4. In winter we are right on the mountain giving you a true ski in ski out. In summer the rivers the mountain and hiking is right out our back door as we enjoy mountain biking hiking golfing and relaxing around the mountain environment. Our unit is well equipped for a wonderful vacation

Guest favorite

Home in Dover

4.97 out of 5 average rating, 39 reviews

3bd Mt.Snow condo: Fireplace and ski off trail.

Coveted Bears Crossing townhouse in the heart of Mount Snow. Less than 3 minutes to the main lodge with direct access to the complex from the ski-home private groomed trail. Offers direct shuttle service to Mt. Snow. You will have full access to the beautiful community center, which has a seasonal heated pool (open from Memorial Day- Labor Day), tennis courts, ping pong table, billiards, TV and fitness center for all year round use. There is also a BBQ area and a large gas fire pit. * no a/c

Guest favorite

Home in Winhall

4.95 out of 5 average rating, 122 reviews

Summit View Ski and Golf Retreat w/hot tub & Sauna

Summit View Chalet @ Stratton is the ideal VT retreat, Minutes from Manchester, directly across the entrance from Stratton's 27 Hole Championship Golf Course. Beautifully remodeled! Relax in the hot tub on the deck with direct summit views in any season. Enjoy shuttle access to lifts, minutes from snowmobiling, hiking, fine dining and shopping. Comfortable accommodations for 6 adults and 5 children. Perfect for 2 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

Guest favorite

Home in Wilmington

5 out of 5 average rating, 13 reviews

Rustic home near skiing & lakes, walk to downtown

This updated home exhibits rustic charm while also being situated in the perfect location. Spend time with friends and family in this 5 bd, 2 bath home that boasts a large kitchen / dinning room for entertaining. Enjoy the nearby skiing, lakes, hiking within a few miles. Walking distance to downtown where you will be enamored by the many restaurants, bars, breweries, and shops. There is also a one of a kind game room with enough room for all! Come experience Vermont the way it should be.

Guest favorite

Condo in Dover

4.94 out of 5 average rating, 35 reviews

Ski in Ski out condo great location

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.

Guest favorite

Condo in Londonderry

4.94 out of 5 average rating, 51 reviews

Magical Ski-In/Ski-Out Condo at Magic w/ game room

End your summer mountainside! Relax trailside at Magic Mountain in a ski in/ski out condo. Our 1 bedroom, 1 bath condo sleeps four with a queen size bed and a bunk bed. We have a couch if you add a few more and have a blow-up queen mattress for added sleeping space. The condo has a game room area just down the hall. On the lower level you have access to a locker room to store your skis etc. and a very small fitness area. Outside find picnic tables and fire pits all overlooking the mountain.

Guest favorite

Condo in Stratton

4.94 out of 5 average rating, 147 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.*

Guest favorite

Rental unit in Dover

4.95 out of 5 average rating, 19 reviews

Mt Snow Condo, 2 Bdrm-Free Ski Shuttle

2 bdrm condo with complete kitchen (all new appliances this year!) and large dining table. Guests have access to a heated indoor pool, sauna, hot tub. We now have 100 Mbps fiber internet and a dedicated office for remote work. It's only a 5 min free shuttle from our front door to Mt Snow base lodge. Besides great skiing there is Mountain Biking, Hiking, Fall Foliage, Fishing, Kayaking, Apple Orchards and great restaurants nearby. A wonderful spot to enjoy VT all year round!

Guest favorite

Condo in Dover

4.87 out of 5 average rating, 228 reviews

Mt Snow Ski In/Out at Seasons

Directly on the mountain. Minutes walk to 2 trails. Full kitchen, dishwater, washer/dryer, microwave. Fireplace with free wood. Large screen TV in living room and tv in each bedroom. Plenty of board games. King size bed in Master. Free parking for 2 cars. Ground floor with deck with tables and chairs for relaxing. Free parking. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.

Superhost

Condo in Dover

4.87 out of 5 average rating, 76 reviews

Cute, Cozy Condo at the base of Mount Snow

Cute, cozy condo located right at the base of the new Carinthia Base Lodge at Mount Snow. Enjoy the convenience of the Grommet Trail and the Magic Carpet access lift just steps away or the Nitro Lift located in the back. Our bright, open floor plan condo has views of the mountain. Full kitchen, fireplace, wifi. Ideal for a family of 4 or two couples. This is our second home and we are interested in working with people who will respect our property.

Guest favorite

Condo in Stratton

4.99 out of 5 average rating, 91 reviews

Luxury Stratton condo just steps to the lift!

Enjoy this beautifully renovated 1 bed/1 bath condo with a live fireplace conveniently located steps from the mountain and Stratton Village! The Tamarack chair lift is only a few hundred yards away! Washer and dryer in unit to warm up your wet clothes after a long day of skiing or mountain biking. Fully stocked kitchen, 50’ TV w/ AppleTV, cable, Amazon Alexa, 5G WiFi, Firewood and more! This is one of the nicest Ober Tal condos available for rent!

Superhost

Home in Dummerston

4.96 out of 5 average rating, 127 reviews

The Sugar House

The Sugarhouse is a fully furnished one bedroom cabin, with a complete kitchen, bathroom with shower and open living / dining room area. It is located on a quiet Vermont country road bordered by historic New England dry stone walls, maple trees, and the beautiful Scott Farm. You can hike, bike, or snowshoe right out the front door. While you’ll feel a world away, you’ll be only 5 miles from Interstate 91 and 10 minutes from Brattleboro or Putney.