
Ski-in/Ski-out holiday 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.

Lovers Honey Pond Treehouse with hot tub & sauna
Guest Favorite VERY romantic abode…The Honey Pond Treehouse is made for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…Enjoy private hot tubbing, sauna time, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes or enjoy our own groomed trails for Xcountry & snowshoes & nature walks!! High speed WiFi 🐣

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

Slopeside Condo @ Seasons on Mt Snow (Ski-In/Out)
Escape to the mountains & stay in our fully equipped 3 bedroom (ski in/out) condo. Enjoy the wood burning fire (wood provided), smart TV & boardgames as well as the fabulous Seasons on Mt Snow facilities where you can relax in a hot tub, pool or sauna. Our ski in/out location is the best on the mountain, between the main face & Carinthia Freestyle Park! See below for info on activities in the warmer months which include hiking, biking, scenic rides, lakes, golf, camp, a spa & the fall colors!

Beautiful Bromley/Manchester VT Retreat w/hot tub
"Manchester Moose!" Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester, Beautifully remodeled VT vacation getaway nestled in the Green Mountains. Closest skiing to quaint Manchester VT, minutes from snowmobiling, hiking, fine dining and shopping. This home features 5 bedrooms, 3 with queen beds including 2 Masters, and 2 bedrooms with double bunks. Perfect for 2 or 3 families to enjoy any season in Southern Vermont's beautiful Green Mountains! YouTube video link @GreenMountainStay

MtSnow* HotTub* Pool * AirHockey* PingPong * Darts
Welcome to our ❄newly listed❄lodge style home! HOT TUB✅ Our home is located on private 2.6 acre lot with beautiful views of Mount Snow in the distance. Our home offers easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our home. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in southern Vermont!

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna
Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

Summer in the mountains!
My slopeside condo miraculously morphs into the perfect Summer mountain getaway. Overlooking the west river valley with views for miles of the greens. With the ski trails to hike and the Appalachian trail running up and around the back you’ll be sure to get your steps in. I sit across the street from the heated pool, tennis courts and clubhouse with full gym. Enjoy the adventure park at base all summer and the never ending shopping and dining down the hill in Manchester. And live music galore!

Game Room, near skiing and lake, 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 gameroom with enough room for all! Come experience Vermont the way it should be.

Magical Ski-In/Ski-Out Condo at Magic w/ game room
Relax trailside at Magic Mountain in a 1 bedroom, 1 bathroom ski in/ski out condo. Best suited for 4-5 guests with a queen size bed and a bunk bed. We have a massive couch if you add a few more. Great proximity to Bromley, Stratton, Okemo and Viking Nordic Center. 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.

Cozy Mt Snow Ski In / Out
Directly on the mountain. Ski right back to 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 each bedroom. Ground floor with private deck with tables and chairs for relaxing. Free parking. Condo across the hall is also available for larger groups. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.

Stratton walk on/off, walk to village, fireplace
This Obertal 1 bedroom 1 bathroom is PERFECT for your weekend and week long getaways to Stratton! After a long drive, park and unload your car and don't worry about her for the rest of your stay! With the mountain just steps away you can walk to skiing/riding, apres drinks, dinner, music, and shopping! • 1 bedroom (Queen) • 1 bathroom • 1 pullout sofa in the living room (Full/Queen) • Walk on/off skiing/riding • Walk to Village (food, drink, shops) • Fireplace

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!
Popular amenities for Windham County ski-in/ski-out rentals
Ski-in/ski-out house rentals

The Sugar House

Private chalet | hot tub, shuttle & ski home trail

Entire Craftsman House Rental

Ski In/Ski Out Mount Snow Condo.

Mt Snow Townhouse - Ski On/Off

SnowBridge Stratton Ski in/Out Trailside 4 Bdrm

Village Watch Ski-in/out Condo in Stratton, VT

5.2milesSkiing/CozyCabin:HotTub/Mount Snow
Family-friendly, ski-in/ski-out home rentals

Renovated Condo - 5 min walk to Mount Snow

SnowTree Chalet- Walk to lifts! 1 bedroom + Loft

The Brook & Ember Condo - Walk to Mount Snow

Cute, Cozy Condo at the base of Mount Snow

Dog-friendly, 1-bedroom apartment w/ fireplace (A)

Luxury Duplex Condo·Stratton Ski in Ski Out

Memorial Day at Stratton. Bike park opens!

Spring at Mount Snow! Biking, Tennis, Pool, Sauna
Ski-in/ski-out condo rentals

Ski On/Off 2BR w/Pool, Fireplace & Arcade

Perfect 3 Br. Getaway Condo in Stratton, Vermont!

Ski In/Out, Cozy 3Bed condo steps to Village

Great Amenties-Seasons Condo gym-sport center-pool

Your Vermondo awaits: Steps to Lifts & Village.

A Village location, Steps to the Lifts & Village

Hiking, biking, pool, Mt. Snow with direct access!

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck
Destinations to explore
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- Ski-in/ski-out rentals Vermont
- Ski-in/ski-out rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Killington Resort
- Berkshire East Mountain Resort
- Monadnock State Park
- Stratton Mountain Resort
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Pico Mountain Ski Resort
- Bousquet Mountain Ski Area
- Fox Run Golf Club
- June Farms
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- National Museum of Racing and Hall of Fame
- Mount Sunapee Resort
- Hancock Shaker Village
- Emerald Lake State Park
- Crotched Mountain Ski and Ride
- Rensselaer Polytechnic Institute
- University of Massachusetts Amherst
- Smith College





