Vacation rentals in Bennington County

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Top-rated vacation rentals in Bennington County

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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, 351 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!

Top guest favorite

The entrance to the guest house displays a dark wood-paneled exterior with a black door featuring a grid window. A small window is positioned beside the door. Recessed lighting illuminates the covered porch area above.

Guesthouse in North Bennington

4.99 out of 5 average rating, 278 reviews

Birch House - lake, green trees + modern comforts

We're a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, air conditioned space w/ cozy, minimalist vibes. A small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. IG birchhousevt Please note that due to a severe allergy, it is difficult to accommodate animals

Top guest favorite

Tiny home in Wilmington

4.99 out of 5 average rating, 298 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Top guest favorite

The colonial home features a classic white exterior with black shutters and a welcoming front porch. An American flag is displayed prominently, and soft outdoor lighting highlights the entrance. The well-maintained lawn includes neatly trimmed bushes, creating a warm first impression.

Home in Sandgate

4.99 out of 5 average rating, 119 reviews

Country Colonial Home with rolling fields & stream

This wonderful colonial home offers wide open space on 21 acres of rolling fields with paths leading to the Green River. In the summer build your own dam or in the winter cross country ski along the edges of the stream and get a full view of the West Arlington valley. Swearing Hill is located within a mile of an old country store for all types of immediate supplies. The town of Arlington is 5 miles away, and Manchester, Vt. Is 14 miles, offering golfing, shopping, and wonderful restaurants.

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

4.99 out of 5 average rating, 256 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.

Top guest favorite

A spacious living area features high vaulted ceilings with exposed wooden beams and large skylights. Natural light illuminates the modern decor, including a comfortable couch, sleek bar stools, and a central coffee table. A fireplace is positioned beside expansive windows that offer views of the surrounding forest.

Cabin in Shaftsbury

4.99 out of 5 average rating, 281 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

A charming cottage is set in a green, open yard, surrounded by tall trees. A white fence encloses the property, with a small flowerbed in front. A rustic red barn is visible in the background, complementing the tranquil rural setting.

Farm stay in Bennington

4.98 out of 5 average rating, 195 reviews

The Farm cottage

Take a break and unwind at this little peaceful oasis. A little bit of the country is right beside you with the neighing of horses and the clucking of chickens who roam our property. We are close to Bennington College and great restaurants and Robert Frost house. We are 35 minutes from Manchester that has some great restaurants and shopping. Bromley ski resort is just beyond Manchester in Peru Vermont . It is a year around resort with water slides in summer and skiing in winter .

Guest favorite

A cozy loft space features a spacious bed dressed in soft linens against a backdrop of large windows. A small dining area with tall chairs is positioned near a wall-mounted TV. Solid wood flooring enhances the warmth of the room, complemented by natural light from the roof skylight.

Guesthouse in Arlington

4.97 out of 5 average rating, 172 reviews

Cozy Log Cabin Suite [100+ Reviews 4.98 Rating]

Welcome to a cozy log cabin loft on private property. Our 600+ square foot suite is consistently upgraded for our guest. You'll enjoy high end accommodations, solid wood flooring, AC, 50" TV with Cable, wireless internet, premium King size bed, fridge and kitchen. Cleanliness has always been a top priority for our guests. We are proud to hold a 5-star rating. As a Registered Nurse in our local hospital, I can assure you we are cleaning and disinfecting following the CDC guidelines.

Top guest favorite

A charming log cabin is surrounded by vibrant autumn foliage, showcasing a dark wooden exterior and a sloped green roof. The mountains in the background provide a scenic view, enhancing the peacefulness of the property, which is set on a gravel driveway.

Cabin in Sunderland

4.98 out of 5 average rating, 109 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!

Top guest favorite

An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.

Cottage in Shaftsbury

4.98 out of 5 average rating, 709 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 250 acre property.

Top guest favorite

A spacious great room features a comfortable seating area with a white couch, eclectic armchair, and colorful floor design. Artistic decorations are placed on the walls and shelves, with a kitchenette visible in the background. A piano and drums are positioned nearby for guest use.

Guest suite in Wilmington

4.92 out of 5 average rating, 787 reviews

Architectural GuestSuite

The Guest Suite is located on the first floor of an architectural studio in historic Wilmington, Vermont. Please enjoy the piano, drums, and art supplies! The Guest Suite is both UNIVERSALLY ACCESSIBLE, TOBACCO FREE, and ANIMAL FREE due to allergies in our family. LineSync Architecture staff will be working from 8:30am - 5ish upstairs, and once in a while on the weekends. When guests are in we try to be super sensitive and quiet, but footsteps will be heard!

Top guest favorite

Two wooden chairs are positioned on a grassy area, facing a gently sloping hill. A modern white farmhouse is visible alongside a deck with stairs. In the background, trees frame the serene landscape, and mountains are faintly visible under a cloudy sky.

Apartment in Bennington

4.91 out of 5 average rating, 186 reviews

Scenic Vermont Studio

This beautiful retreat is halfway between the ski slopes of southern Vermont and the cultural centers of Williamstown and North Adams, MA. The residence is a modern, spacious, basement apartment, part of an 1860 farm house. It has its own private entrance around the back of the house at ground level. Solar garden lights and motion detector lighting will illuminate your path to the apartment.