Cabin vacation rentals in Windsor County

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Top-rated cabin rentals in Windsor County

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Guest favourite

Cabin in Royalton

4.99 out of 5 average rating, 197 reviews

Genuine Vermont Sugar House on 70 peaceful acres.

Stay in this genuine Vermont sugarhouse. Our family took great pride in making Maple Syrup and now we take that same pride in sharing this private piece of Vermont with you, our guests. There are trails that will take you through our 70-acre property including the sugar bush we used for the sugarhouse. Relax in the quiet beauty of rural Vermont. Located near the geographical center of VT. We do welcome friendly housebroken dogs. Please see other details under show more. Part of Three Maples LLC.

Guest favourite

Cabin in Randolph

4.95 out of 5 average rating, 140 reviews

Remote, pond view log home, fully loaded, sleeps 6

Enjoy our remote, easily accessible, immaculate, pond-side cabin, set in nature on 109 acres: pond, woods, fields, and trails; with high-speed internet and smart TV! Sleeps 6, including a queen bed, 2 bunk beds, and a sleep sofa. Fully equipped kitchen, including a full-sized refrigerator, microwave, Keurig coffee maker, and many other amenities. Screened in porch. Views from every room! In the heart of the Vermont ski corridor. Explore the trails, and our meditation yurt when available!

Guest favourite

Cabin in Bridgewater Corners

4.82 out of 5 average rating, 191 reviews

Cozy Mountain Cabin Close to Killington &Woodstock

Find us on IG @offpistepropertiesvt and TikTok @offpistepropertiesvt Our cozy cabin is close to Killington Mountain (5 min. to Skyeship, 10 min. Snowshed) or Okemo (20m), Long Trail (2 mi) Woodstock (15min). So much to do in the area all year! You will get the quiet, clean, and coziness of a cabin, but RUSTIC and renovated. Relax and unwind! Our professional cleaning company provides a spotless, meticulously cleaned cabin with professionally laundered linens… we charge you what we pay!

Guest favourite

Cabin in Royalton

4.93 out of 5 average rating, 266 reviews

Scandinavian design Cabin w/ private hiking trail

*NEW FROM JULY '24: a Goodland Wood Burning Hot Tub* Welcome to our charming cabin nestled in the heart of the woods, where comfort meets tranquility. This 400 sq. ft retreat is bathed in natural light, boasting high-quality appliances, strong WiFi and thoughtfully curated design furniture to ensure a cozy and memorable stay. Conveniently located near several ski resorts (Saskadena 6, Killington, Stowe) , the pristine White River, and picturesque villages like Woodstock, VT.

Guest favourite

Cabin in Mount Holly

4.97 out of 5 average rating, 221 reviews

Private Cabin/PetsOK/Minutes to Okemo/AC/Fast Wifi

Enjoy the beauty of Vermont at our private cabin. Situated on acres of woods next to a small creek, the cabin is 15 minutes to Okemo Mountain, excellent hiking on the Appalachian Trail and scenic Vermont towns for dining and shopping. With a queen bed loft, a double bed bedroom and a pull out sofa, the cabin sleeps up to 4 people. The kitchen is nicely equipped and there is a charcoal grill outside. High speed fiber optic internet will keep you connected. Max 2 pets allowed.

Guest favourite

Cabin in Hancock

4.95 out of 5 average rating, 234 reviews

Hancock hideaway

Skiing, snow biking 10 minutes away at Middlebury Snow Bowl and Rikert crosscountry. Sugarbush and Killington half hour drive. Snowshoeing and hiking right behind house in the Green Mountain National Forest. Easy drive to river swimming holes and lakes. Excellent restaurants in Waitsfield and Middlebury - about half hour. Good restaurant, cafe, small grocery store, in Rochester, 4 miles. Great location, beautiful views, lovely little house, totally private, romantic.

Guest favourite

Cabin in Woodstock

4.98 out of 5 average rating, 184 reviews

Cozy Log Cabin, Peaceful Retreat

Cozy Cabin doesn’t charge an additional cleaning fee to our guests! We focus on a comfortable, relaxed, Vermont experience. If you’re looking for a peaceful, yet accessible location, we are situated on 15 acres located between Woodstock Village & Killington. There’s fiber WiFi, Hulu +Live TV w/local channels, ESPN+, Disney+. Also Amazon movies & music, Netflix, Paramount+, & Peacock. The Rec Room has a pool table, darts, lounge, gym and a desk for remote work.

Guest favourite

Cabin in Chittenden

4.96 out of 5 average rating, 105 reviews

Cabin on The Hill

Relax with the whole family at this peaceful place. Private, cozy, clean, comfortable getaway in Chittenden Vermont. This beautiful cabin is off the grid with solar power and push button generator. Chittenden is a small drive to endless recreational activities for every season. It is the perfect rustic space for a couple or a small family. It is centrally located between Killington and Rutland. Everything you need is within a 20 to 30 minute drive.

Guest favourite

Cabin in Rochester

4.95 out of 5 average rating, 424 reviews

Black haus: a hip, cool house hidden in a forest.

You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

Guest favourite

Cabin in Mount Holly

4.91 out of 5 average rating, 129 reviews

Camp Mt. Holly - modern cabin by Okemo & Ludlow

Welcome to Camp Mt. Holly: your own 16-acre, cabin retreat in the Green Mountain National Forest! Camp Mt. Holly features mid-century modern decor, modern amenities, wood stove, fire pit, private trails and river (complete with a secret spot to wade in the water). Only 15 minutes to Okemo Mountain and the town of Ludlow, which features some of the best restaurants, bars, and shopping in central Vermont! Pets welcome with a $100 pet fee!

Guest favourite

Cabin in Hancock

4.97 out of 5 average rating, 357 reviews

Funky, family-friendly cabin

Our funky, fun house is nestled in the woods, with a waterfall and brook rushing by outside the large wall of windows. Situated in the Green Mountains, this is the perfect place to relax and play. The large open-floor plan is perfect for families with school-age children. Families with infants and toddlers may not find our home as friendly, as the waterfall, loft and attached farm buildings may create some safety challenges.

Guest favourite

Cabin in South Royalton

4.95 out of 5 average rating, 152 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.