Cabin holiday rentals in Windsor County

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Top-rated cabin rentals in Windsor County

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Superhost

Cabin in Ludlow

4.78 out of 5 average rating, 110 reviews

Cozy Log Cabin | 5 Min to Ski | Great for Groups

Also available for long-term rent. Please inquire for more details. A 3-minute drive from downtown Ludlow & Okemo Mountain Resort, this recently renovated cabin is located on a private drive right off RTE 100. It's the perfect location for any seasonal activity you've come to enjoy - skiing, hiking, swimming, leaf peeping, etc. Finish any day lounging at the cabin or out on our oversized deck or head into town for your choice of wood-fired pizza, cozy taverns, breweries or wine/cocktail bars.

Guest favourite

Cabin in Randolph

4.95 out of 5 average rating, 156 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!

Top guest favourite

Cabin in Stockbridge

4.95 out of 5 average rating, 107 reviews

1958 Classic "Hunting Cabin" w/ Breathtaking Views

Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Originally purchased from a Sears & Roebuck catalog as a hunting cabin owned by the same family until 2019. The cabin has since been transformed into its original vintage classic camp décor with antique furnishings and unique vintage finds that take you back in time.

Guest favourite

Cabin in Sharon

4.92 out of 5 average rating, 262 reviews

Cozy secluded ‘birds nest’ off-grid cabin

Back to basics living, simple rustic charm, circa 1900 cabin in the woods getaway, spend time in nature surrounded by forest, brook, wildlife, hiking trails, fall foliage. Close to Woodstock and S. Royalton, fully off-grid. No electricity or plumbing, yet lanterns and fresh water jugs provided. Unwind from the outside world and reconnect with your self or your loved ones and the natural world around you. Loft with real beds, well stocked kitchen, propane oven, grill, outhouse, Glamping!

Top guest favourite

Cabin in Landgrove

4.99 out of 5 average rating, 180 reviews

The Owl’s Nest in Landgrove

Our recently renovated cabin is the perfect escape during any season! Located within minutes of Bromley, Magic, and Stratton, Wild Wings, and Viking. Also nestled in an amazing network of hiking, biking and ski trails. Guests will never be more than a few minutes away from outdoor adventure. With two bedrooms and one bonus loft, guests can enjoy the comforts of our cozy cabin, including a full kitchen, bathroom, outdoor shower, HOT TUB, fire pit, WiFi and FREE EV CHARGING. @owlsnestvt

Top guest favourite

Cabin in West Windsor

4.97 out of 5 average rating, 242 reviews

Sunset Cabin - your private romantic hideaway

Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; this rustic, pet friendly cabin is a perfect romantic hideaway. Two trout ponds are steps from your door for fishing and swimming. Just minutes from Mt. Ascutney's hiking/biking trails and in the middle of fantastic cycling country. Near local race including the VT100, Vt overland, VT50. Sunset Cabin is a marvelous spot for enjoying fall foliage and exploring VT!

Superhost

Cabin in Bridgewater

4.91 out of 5 average rating, 100 reviews

100 Acres Views & Creek near Woodstock/Killington

You will leave the demands of your busy lifestyle behind when you vacation on our 100+ acre 4 BR 2 BA cabin property with a babbling crystal clear mountain creek. Place your beach chair in the creek, relax with your favorite book for Best Spa Experience Ever! Large open covered porch with porch swing seating to enjoy the expansive mountain views, listen to the leaves rustle and the stream running in the distance. Miles of hiking & biking trails, skiing, restaurants and more nearby.

Guest favourite

Cabin in Royalton

4.94 out of 5 average rating, 300 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.

Top guest favourite

Cabin in Mount Holly

4.98 out of 5 average rating, 241 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 Pittsfield

4.98 out of 5 average rating, 154 reviews

Tiny Vermont Cabin!

Newly built tiny cabin in the woods of Vermont! Perfect for a quiet get away and close by outdoor fun! Killington and Pico Mountain is 15 minutes away! Sugarbush is 50 minute drive. Coming to Pittsfield for a wedding? Riverside Farm is only .7 of a mile down the road! MUST have AWD/4x4 for winter access on dirt road and driveway. Cozy up by the newly added propane fireplace with an easy click of a button! Come experience the winter beauty Vermont has to offer!

Top guest favourite

Cabin in Woodstock

4.98 out of 5 average rating, 194 reviews

Cozy Log Cabin, Peaceful Retreat, April Savings!

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 with Starz, MAX, +Live TV w/local channels, ESPN+, Disney+. Also Amazon movies & music, Netflix & Peacock. The Rec Room has a pool table, darts, lounge, gym and a desk for remote work.

Guest favourite

Cabin in Fairlee

4.95 out of 5 average rating, 138 reviews

Fairlee Log Cabin

Cozy Log cabin 0.2 miles from Lake Fairlee! This year-round cabin is a cozy getaway from the hustle and bustle of life. Just two hours north of Boston, and 30 minutes from Dartmouth, Lebanon, and the White River Junction. Additional amenities: -Clawfoot tub -Outdoor firepit -40 acres of land for hiking, mountain biking, snowshoeing, etc. -dog only friendly for a $40 additional fee -**as of 2/1/23 new oven and dishwasher :)