Ski-in/out vacation rentals in Windsor County

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 🐣

The Grateful Barn

THE GRATEFUL BARN IS BACK! Renovated 1800's Vermont guest barn. Located on National Forest RD & land locked by the Green National Forest. The Grateful Barn is a guest cabin located next to a seasonal country home. The Grateful Barn offers a private bedroom with a queen sized bed, 2 single beds in the music loft and a pull out double bed in living room. Recently remodeled bathroom with walk in shower. This remote VT location is a few steps from the Long Trail & 7 minute drive to Bromley Mountain

Cozy cottage near Killington & Sugarbush

Escape the real world at this charming and cozy cottage tucked away in a corner of 17 acres of rolling grassy hills. Take in the unmatched views of the hollow from the living room or wrap-around porch. Endless nearby trails for hiking/biking/xc skiing, and Rochester's stores, cafes, and restaurants are less than 10 minutes away. Grocery store, berry picking, lakes, swimming holes, golfing, restaurants, breweries, and wineries all within an easy drive. Killington/Sugarbush both ~35 minutes away.

Ski on Ski off killington/ Pico mountain condo

Beautiful ski on ski off condo at the foot off Pico mountain ski resort. Free shuttle bus to Killington and Rutland at front door. 4th floor (top floor) condo with elevator. Balcony with view of Dears Leep overlook. Quiet top floor end unit. Full kitchen, 1 bedroom with seperate living room. Living room has pull out sofa bed and 54 inch t.v. and WIFI. Hike the Appalachian, Long and Catamount trails from your back door. 30 minutes from Woodstock. Please be sure to read and agree to house rules.

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.

Yurt In The Woods - Private Refuge

The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for Weekends. October 6th and 12th are currently vacant if you want a fall foliage trip. There is a "one" night stay fee of $50 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available May - October

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.

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

Experience year-round adventure at Sunrise Village at Killington, just steps from scenic trails and the Sunrise Village Triple Lift (488 ft away). After a day of outdoor fun, unwind by the cozy gas fireplace. Explore nearby hiking, mountain biking, kayaking, and golfing. The indoor sports complex—featuring a pool, hot tub, and gym—is a short walk away. Perfect for outdoor lovers looking to relax and make unforgettable memories!

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.

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!

Cozy Mountain Condo

Updated 1 Bdr Whiffletree condo in the heart of Killington minutes from everything. The condo is fully stocked with all of the essentials you will need for your Vermont get away. Ski locker for all your gear! Sleeps up to 4 with a king bed and queen pullout sofa. Shuttle in/out service available weekends (Dec–April), or ski home when conditions allow (check Killington trail status). Killington Reg #004858

CozyDen-Location, Fireplace, Ski Off/Shuttle On!

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!