Cabin vacation rentals in Bennington County

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Top-rated cabin rentals in Bennington County

Guests agree: these cabins are highly rated for location, cleanliness, and more.

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Top guest favorite

The rustic cabin features a red exterior with a metal roof, framed by lush greenery. Flower pots with colorful blooms adorn the porch, which includes a small table and chairs. Large windows allow natural light to illuminate the interior.

Cabin in Londonderry

4.94 out of 5 average rating, 348 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Superhost

The custom home features warm wood siding and a welcoming porch with flower boxes. A spacious deck with rustic railings extends from the second floor, while a covered area includes seating. Surrounding greenery enhances the natural setting, creating a serene outdoor ambiance.

Cabin in Wardsboro

4.84 out of 5 average rating, 144 reviews

Mountain side acres

10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Top guest favorite

A newly built log cabin displays charming wooden siding and a stylish metal roof, surrounded by lush greenery. A small porch with steps leads to the entrance, while a gravel area provides access to the cabin. The sky above is clear with a few clouds.

Cabin in Stratton

5 out of 5 average rating, 160 reviews

Log Cabin, King Beds & AC Near Hike/Swim/Golf/Bike

Kick back and relax in this calm, stylish, newly built log cabin which was finished in early 2022. Fully equipped with stainless steel appliances, soapstone counters, central a/c, all new furniture, mattresses and bedding. First floor master bedroom leads into a large, covered, screened in porch, which is perfect for your early morning coffee or evening cocktails. Starlink high speed Wi-Fi and a smart tv in the living room and bedroom. 7 Minutes from Stratton Mtn, 15 from Mt Snow. Nearby lakes!

Top guest favorite

An inviting cabin exterior features a combination of natural wood and a metal roof. A spacious deck is visible with seating arrangements and a small table, surrounded by lush greenery. The setting reflects a tranquil hillside ambiance, enhanced by the picturesque sky above.

Cabin in Rupert

4.99 out of 5 average rating, 103 reviews

Elegant & Rustic VT Cabin - A Peaceful Getaway.

Nestled on 10 hillside acres just outside the small town of West Rupert, our cabin offers a relaxing "get-away-from-it-all," yet is convenient to all that southern VT and eastern NY has to offer. Perfect for a romantic weekend with a special someone, a relaxing country vacation with family, or a fun retreat with good friends. 3 BRs (plus sleeping loft) and full bath. Hike, bike, ski, golf, fish, shop, swim, dine, antique, explore, etc...or just relax and do nothing. Make yourself at home!

Top guest favorite

A cozy cabin is depicted in a snow-covered landscape. The structure features a spacious deck with wooden railings, surrounded by tall trees. Snow blankets the ground, creating a serene winter scene. Firewood is neatly stacked beside the cabin, adding to the rustic charm.

Cabin in Woodford

4.95 out of 5 average rating, 115 reviews

Charming Cabin with 2 baths in the Green Mountains

A cozy cabin nestled high up in the green mountains. A perfect getaway on a quiet street. This home is located in between the towns of Bennington and Wilmington. Across the street from Prospect Mountain (cross-country skiing and snow shoeing) and about 25-30 minutes to Mount Snow (downhill skiing). Vast snowmobile trail in our backyard. Visit the quaint general store nearby or go hiking in Woodford National State Park. At 2,000 ft elevation, the stars are on stage when it's a clear night.

Top guest favorite

The cabin's exterior showcases a warm wooden facade with large, strategically placed windows. A spacious screened porch extends from the building, inviting natural light and outdoor enjoyment. A stone pathway leads to the entrance, surrounded by landscaped gravel and native vegetation.

Cabin in Jamaica

5 out of 5 average rating, 253 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Guest favorite

Cabin in Londonderry

4.94 out of 5 average rating, 145 reviews

Vintage Vermont Cabin, Hot Tub, Fire Pit, Private

We can’t wait to host you at Deerwood Hill in Londonderry VT! Featured on Levi Kelly's Cabin Tours! 🌲 Deerwood Hill is a private 3.6 acre private lot 🎿 Within minutes to Stratton, Magic, Bromley, Mt Snow, & Okemo ski resorts! 1 hour to Killington! 📍 Under 30 minutes to wonderful Manchester! ⛰️ 5 miles to Lowell State Park, 8 miles to Appalachian Trailhead ♥Sleeps 6 ♥2nd Bedroom is open loft with full bath ☒ Booking Guest must be 25. ☒ NO PARTIES, NO SMOKING, NO PETS @deerwoodhill

Top guest favorite

A midcentury modern cabin is nestled among trees, its dark exterior contrasting with the fresh snow covering the ground. A spacious deck is visible, adorned with wooden railings, while large windows reflect the serene winter landscape.

Cabin in Shaftsbury

4.99 out of 5 average rating, 278 reviews

The Hygge Loft- mid-mod cabin on 70 forested acres

The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

Top guest favorite

Cabin in Landgrove

4.99 out of 5 average rating, 188 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 favorite

The log cabin, featuring a green roof, is surrounded by snow-covered ground and trees. Large windows reflect the soft light of sunrise or sunset, while the outline of the peaceful mountain landscape can be seen in the background.

Cabin in Sunderland

4.98 out of 5 average rating, 107 reviews

The Birchwood Cabin - Stunning Mountain Views

Welcome to the Birchwood Cabin - a beautiful log cabin with stunning mountain views! Relax in the hot tub overlooking the mountains or enjoy hot chocolate by the fire. Play a game of pool or shuffleboard downstairs. The Birchwood Cabin is in a peaceful, quiet location but is only a 10-minute drive to Manchester, if you'd like to go shopping or grab a bite to eat! Hit the slopes at Bromley Mountain or Stratton Mountain or in the warmer weather head to The Equinox for a round of golf!

Guest favorite

A charming wooden chalet is surrounded by greenery, showcasing a spacious deck equipped with a hot tub and outdoor furniture. A stone patio with a fire pit is positioned in front, creating an inviting area for relaxation and gatherings.

Cabin in Wilmington

4.91 out of 5 average rating, 142 reviews

Chic Chalet | Hot Tub · Clubhouse · Mt. Snow

Escape to The Sugar Maple Chalet, your stylish family retreat in the heart of Wilmington, Vermont. This thoughtfully updated four-bedroom home blends cozy charm with modern comforts—think high-speed Wi-Fi, a private outdoor hot tub, and a fun-filled basement bar and game room. Just a few minutes from local shops, restaurants, ski slopes, and scenic hiking trails. One well-behaved pet is welcome to join the adventure! AC installed when temperatures average above 78 degrees.

Superhost

An aerial view of a cabin nestled among dense forest, surrounded by trees showcasing autumn colors. The gravel path leads to the property, revealing a vehicle parked near the cabin. Roofs of two buildings can be seen, along with scattered outdoor areas.

Cabin in Jamaica

4.88 out of 5 average rating, 406 reviews

Cabin-Swim-View-Fire Pit-7 min to Stratton-Dogs OK

Authentic post & beam cabin surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Swimming hole at babbling brook on property, fire pit, hammock on porch, propane BBQ, picnic table, forest views. TV with VCR & videos, turntable & records, games, Satellite Internet & WiFi 20-100 mbps. Staircase to loft, gas heat, wood stove, pellet stove. Full kitchen. Easy to use, odorless composting toilet. Dog friendly.