
Ski-in/Ski-out vacation rentals in Windsor County
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Top-rated ski-in/ski-out rentals in Windsor County
Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.

Killington Chalet, Hot Tub, Sauna, Huge Boot Dryer
The Killington Chalet is your ideal vacation rental in the Green Mountains. It's the Right side of a duplex, perfect for families, couples, and groups. Located just off Killington Rd, it offers a secluded retreat near slopes, restaurants, and outdoor activities. Enjoy skiing, boarding, mountain biking, and more. Features include hot tub, sauna, boot dryer, wood stove, fire pit, and a fully equipped kitchen. Fresh linens, towels, and toiletries provided. Book for a memorable stay in every season!
ValueFamilyNearby
4.84 out of 5 average rating, 264 reviews
Topridge 3BR w Incredible View & Private Hot Tub!
Oso Dream provides AMAZING panoramic views of Bear Mountain. Step out the front door and ski down Sundog trail to Sunrise Village Triple or step out the back door and hop onto Bear Cub trail to access Bear Mountain! Enjoy the amenities within the complex including indoor & outdoor heated pool (seasonal), sauna and gym. Guests also have access to the outdoor skating rink and xc ski trails (weather permitting). Free use of ice skates, puff hockey equipment, snow shoes, xc skies, poles and sleds!
FamilyValueAccess
4.93 out of 5 average rating, 113 reviews
Midcentury Hillside Retreat - Summer Paradise
Enjoy this peaceful retreat in the heart of the Green Mtns and surrounded by 130+ acres of private woodland. Dramatic field stone fireplace and spectacular panoramic views of Mt Ascutney into New Hampshire from the entire living space. Large chef's kitchen. Private master suite and two guest bedrooms. The perfect get-away for relaxing with family and friends. Exceptional hiking, biking and Connecticut River adventures. Near GMHA and Woodstock. Great restaurants, fun village shopping nearby.
FamilyValueDecor
5.0 out of 5 average rating, 134 reviews
Cabin on the Hill
Enjoy a stay in the hills of Vermont - glamping at its finest! A 5-10 minute hike UPhill to a secluded getaway in the heart of Vermont. Amenities include a quaint outhouse, a unique outdoor shower, a 2 burner outdoor gas stovetop and a fire pit to roast marshmallows. The 12x14 screened in cabin with ladder accessed loft sleeps 2 comfortably. Don't worry about bringing pots and pans - cabin is equipped with dishes and a water supply. Adjustable LED lights to light up the night.
FamilyValueHospitality
4.97 out of 5 average rating, 240 reviews
Alpine Condo - AC & Pool - Golf & Bike
Updated 1-bedroom Whiffletree condo with stylish alpine feel—steps from Killington Resort, golf course, and access road. Thoughtfully stocked with essentials, plus a private gear locker for convenience. Relax at the onsite outdoor pool (open Memorial Day–Labor Day). Sleeps 4 with a king bed and queen pullout sofa. Portable AC unit in the living room helps keep the condo comfortable Pack & Play crib, mattress and sheets available upon request. Reg #007718
LocationFamilyNearby
4.99 out of 5 average rating, 181 reviews
Yurt In The Woods - Come to the Yurt.
The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. In October, I require a two night stay with the exception of October 4 & 11. There is a "one" night stay fee of $50 - charged as extra services Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network AC, Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available June - October
LocationValueHiking
4.95 out of 5 average rating, 1067 reviews
Golf and Mountain Biking outside the door!
Enjoy Killington at competitive pricing without sacrificing comfort! Located in Trail Creek Condo Association. • Ski, hike, bike, or golf just steps away • Cozy up by the wood fireplace (free wood) • Pool, hot tubs, sauna, and game room at community center • 6-minute walk to Snowshed or shuttle (winter weekends/holidays) • Ski home trail (snow-dependent) • Minutes to restaurants, bars, and shops • Convenient bus stop Adventure and relaxation await!
FamilyLocationAccess
4.89 out of 5 average rating, 139 reviews
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.
ValueFamilyBiking
4.86 out of 5 average rating, 265 reviews
Cozy 4-season Cabin on Pond - "East Cabin"
Take refuge in a cozy log cabin with abundant access to Vermont's Green Mountains and rolling foothills. A quick drive to Woodstock and Quechee, the cabin is located on quiet dirt road with beautiful south-facing views overlooking the town of South Royalton, just a mile away. Spring-fed pond is steps from the cabin, take a dip! Follow the trails through the woods and fields and enjoy this pristine piece of Vermont.
ValueFamilyGetting around
4.96 out of 5 average rating, 237 reviews
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!
ValueFamilyGrill
4.95 out of 5 average rating, 152 reviews
Ski-In/Out, AC, Pools, Hot Tub, Pet-Friendly
Escape to a spacious, pet-friendly 1-bedroom mountain condo in Killington, comfortably sleeping 4. Enjoy year-round adventures with easy access to hiking, biking, golf, and skiing. The condo is 488 ft to the sunrise lift! Relax on your private balcony, by the gas fireplace, or at the resort's indoor/outdoor pools, hot tub, and fitness center. Perfect for a serene mountain getaway with all amenities.
LocationFamilyTV
4.95 out of 5 average rating, 178 reviews
CozyDen - AC, Bike to Mountain, Porch!
Welcome to our cozy 1-bedroom condo in Killington, VT! Ski off and shuttle on, close to everything including biking and golfing. Enjoy the wood-burning stove, comfortable furnishings, and well-equipped kitchen. Rest well in the king bed and explore the slopes, trails, and golf courses nearby. Relax on the porch or by the fire. Your perfect Killington getaway awaits!
ValueLocationCleanliness
4.98 out of 5 average rating, 213 reviewsPopular amenities for Windsor County ski-in/ski-out rentals
Ski-in/ski-out house rentals

1st floor, Okemo contemporary country 3 BR 2 BA
ValueLocationSleep quality
4.88 out of 5 average rating, 153 reviews
Classic VT Ski Chalet - Walkable to Okemo Ski Lift
LocationValueAccess
4.92 out of 5 average rating, 114 reviews
Renovated Kingswood 3Br | Pool, Golf, Club Access
ValueLocationLayout
5.0 out of 5 average rating, 15 reviews
The Slippery Slope Chalet: Ski-In/Ski-Out Pico
LocationFamilyView
4.83 out of 5 average rating, 29 reviews
Ski-In/Ski-Out Hike Okemo Condo Solitude Village
LocationFamilyPool
4.95 out of 5 average rating, 42 reviews
Killington Condo Near Mountain Biking Trails
FamilyLocationKitchen
4.94 out of 5 average rating, 63 reviews
The Navillus House: Hot Tub, Slopeside, Ski On/Off
FamilyValueBathroom
4.71 out of 5 average rating, 24 reviews
Ski On/Off Sunrise at Killington
FamilyLocationHospitality
5.0 out of 5 average rating, 26 reviewsFamily-friendly, ski-in/ski-out home rentals

Mtn Green Condo-Ski/Bike Lifts, Covered Parking
FamilyValueWalkability
4.92 out of 5 average rating, 226 reviews
Killington-Pico ski in/out Studio at base of Pico
ValueLocationBiking
4.88 out of 5 average rating, 269 reviews
Cozy cottage with Panoramic Views (now with AC!)
FamilyValueHiking
4.98 out of 5 average rating, 118 reviews
Beautiful 2 Bedrooms in Mountains
FamilyValueShared spaces
4.89 out of 5 average rating, 519 reviews
Winterplace - Steps away from Slopes
LocationValueSkiing
4.96 out of 5 average rating, 116 reviews
⭐️Cozy Ski On-Ski Off Wood Fire Place & King Bed
FamilyLocationHeating
4.94 out of 5 average rating, 111 reviews
Okemo Ski-in/Ski-out, Steps to lift Condo
ValueLocationHeating
4.93 out of 5 average rating, 175 reviews
Private Mountain Sanctuary | 15 Min to Killington
FamilyLocationLayout
4.92 out of 5 average rating, 50 reviewsSki-in/ski-out cabin rentals

The Cozy Little Red Cabin
LocationFamilyHeating
4.94 out of 5 average rating, 182 reviews
The Grateful Barn
ValueLocationCleanliness
4.84 out of 5 average rating, 119 reviews
Beautiful Art Studio with hot tub/sauna #1 Airbnb
FamilyValueBackyard
4.75 out of 5 average rating, 437 reviews
THE CABIN....a Vermont log home
LocationValueAmenities
4.85 out of 5 average rating, 254 reviews
Killington Golf&Mtn Biking. Hot tub & Fireplace!
FamilyLocationBathroom
4.79 out of 5 average rating, 28 reviews
Blue Cozy Ski House
FamilyValueAccuracy
4.76 out of 5 average rating, 59 reviews
The music Cabin in Vermont, you will have fun
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- Ski-in/ski-out rentals Vermont
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- Okemo Mountain Resort
- Stratton Mountain
- Pats Peak Ski Area
- Monadnock State Park
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth College
- Tenney Mountain Resort
- Fort Ticonderoga
- Ragged Mountain Resort
- Hildene, The Lincoln Family Home
- Middlebury College
- Killington Resort
- Mount Monadnock
- Bromley Mountain Ski Resort
- Emerald Lake State Park
- Montshire Museum of Science
- Mount Sunapee Resort
- Warren Falls
- Camp Plymouth State Park
- Quechee Gorge
- Jamaica State Park
- Crotched Mountain Ski and Ride
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