Vacation rentals with breakfast in Bennington County

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Top-rated breakfast rentals in Bennington County

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Several free-range chickens are seen pecking at slices of watermelon scattered on a green lawn. The chickens display a variety of feather patterns, including striped and solid colors. A distant structure is partially visible in the background, surrounded by trees.

Tiny home in Shaftsbury

4.51 out of 5 average rating, 142 reviews

Studio style Vintage Garden Bungalow

Studio style guest house set on a 22 acre vintage Vermont farm. You be able to enjoy some of the originality of gardeners quarters together with the renovated and updated space. The bungalow consists of two rooms plus bath, a bedroom with double bed and a kitchenette/sitting area. Kitchenette is equipped with microwave, refrigerator, toaster oven,griddle and complimentary coffee, tea and coco. Out back a Vermont white marble veranda , seating and grill. Shower in bath, complimentary shampoo

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Home in Jamaica

4.93 out of 5 average rating, 15 reviews

The Mountain Escape

Welcome to Stratton Mountain Escape! This spacious 4-bedroom, 3.5-bathroom + loft home is the perfect retreat for families and groups. Enjoy an open-concept kitchen and living room, a luxurious master suite with a jacuzzi tub, or the spacious loft that overlooks the living room. Relax in the huge outdoor hot tub, gather around the fire pit, or unwind on the large deck. Just minutes from Stratton Mountain, this is the ultimate getaway for skiing, hiking, and relaxation. Book your stay today!

Chalet in Dover

4.89 out of 5 average rating, 91 reviews

Moose House: located 5 minutes to Mt. Snow

Mt. Snow entrance is a half mile away! Dover Bar & Grill and Mount Snow Market which sells wine/liquor are a minutes walk also, the MOOVER, which is a free transport to and from the mountain as well as Wilmington, Brattleboro and Bennington. The house is perfect for two families or for a large group to enjoy. The kitchen has everything you'll need, including a gas grill on the front deck. Lots of games, including Xbox and darts! The driveway is able to accommodate up to 6 vehicles.

Top guest favorite

A wooden horse silhouette is displayed on the wall above, showcasing a trotting design in dark green and natural wood tones. Exposed wooden beams add a rustic charm to the space, contributing to the overall tranquil atmosphere.

Farm stay in Bennington

4.98 out of 5 average rating, 174 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 .

Top guest favorite

The image captures an exterior view of the entrance featuring a decorative lantern mounted beside a stylish sign displaying the address '1172 Vail Road.' The muted colors of the siding complement the warm tones of the wooden door.

Home in Bennington

4.99 out of 5 average rating, 318 reviews

Southern Vermont Home

Beautiful home that offers privacy on over one acre of land. It is only a short drive to the conveniences of downtown shopping, restaurants, Bennington College, and much more. This house is 35 minutes from Manchester's famous outlets, 20 minutes from Williamstown, MA, and 45 minutes from Albany, NY. Bromley and Mount Snow ski areas are 40 minutes. The home has wonderful finishes and you will feel right at home upon arrival. Please come explore Vermont from our country escape!

Guest favorite

Two black rocking chairs are situated on a covered porch, accompanied by vibrant potted flowers. An American flag displaying the year '76' waves gently in the breeze. In the background, a glimpse of the Henry Covered Bridge is visible, enhancing the peaceful setting.

Home in Bennington

5 out of 5 average rating, 48 reviews

The Henry House & Authentic Red Covered Bridge

Built in 1769, the house of Lt. William Henry, Revolutionary War Hero and participant in the Battle of Bennington, is listed on the National Register of Historic Places. The Henry House sits on 25 acres of a tranquil setting of meadows and mountains. The original charm of this landmark home is retained for your pleasure in this authentic house our family has rejuvenated. It also features a beautiful open front porch overlooking the Henry Covered Bridge and Walloomsac River.

Top guest favorite

A rustic black exterior home is framed by lush greenery, with a well-manicured lawn and a gravel driveway. The front porch features seating, while neatly stacked firewood is visible beside the garage, enhancing the inviting appearance of the property.

Home in Winhall

5 out of 5 average rating, 19 reviews

Summer in Winhall - Fire-pit, Hot Tub, Sleeps 10

3 Bedroom, 3 Bathroom Sleeps 10 Hot Tub, Fire Pit - 5 minutes from Bromley Mountain - 8 minutes from Stratton Mountain - 15 minute drive to Manchester Bedroom Highlights: - Primary Bedroom: King bed with en-suite bathroom - Second Bedroom: Ideal for families, featuring twin and full bunk beds - Third Bedroom: Queen bed with en-suite bathroom Outdoor Amenities: - Relax in the private hot tub under the stars - Gather around the cozy firepit for evening conversations

Top guest favorite

A detailed ski resort map displays various trails, slopes, and lifts throughout the mountainous terrain. Color-coded paths indicate beginner, intermediate, and advanced runs. Key landmarks and services are marked, alongside a layout of the surrounding area, providing a comprehensive overview of the resort's offerings.

Townhouse in Dover

4.98 out of 5 average rating, 59 reviews

Serene 3Br VT Escape Lakes, Trails, Golf and more

Enjoy the charm of Vermont in our townhouse. All the beauty, serenity and fun of Vermont is right outside our door! Miles of beautiful Green Mountain Forest trails await through trailhead a short walk away. Hiking, watersports, horseback riding, golf, antiquing, or just relaxing... the choice is yours. A delightful smorgasbord of shops and restaurants await only a few mins away. A romantic escape, a family adventure, a restful retreated the Lemondrop lodge is for you.

A charming house features a front porch with rocking chairs, framed by lush green grass and blooming flower beds. An American flag is displayed prominently. Tall trees create a natural backdrop, enhancing the sense of privacy and tranquility.

Home in Manchester

Secluded VT home, close to town and skiing

Lovely, privately situated home (3 bedrooms, 2 1/2 baths, sleeps 6) with the true feeling of Vermont. Around the Property: Plenty of space for lawn games: croquet, horseshoes, badminton, catching fireflies. Golfers can take a 9-iron or wedge out to the 'long yard'. it's ninety yards to the tree line. Strolling, running hiking and biking on Three Maple Drive, one of the prettiest roads in Manchester. Our house is five minutes into town, 15 to Bromley, 20 to Stratton.

Guest favorite

Cabin in Winhall

4.96 out of 5 average rating, 351 reviews

A-Frame Mountain Retreat near Manchester

The Vermont A-Frame is a dog friendly cabin conveniently located on the edge of the Green Mountain Forest. WFH using our fast WiFi + enjoy nature while doing so! Whether your plan is to ski, shop, hike or just relax, the Vermont A-Frame is the ideal place to experience it all. With room for 6 and plenty of amenities, our charming A-Frame is sure to provide you with the perfect home for your Vermont vacation. Find us on social media! @thevermontaframe

Top guest favorite

An open living area features a spacious wooden table accompanied by high-backed chairs, inviting meals or gatherings. A cozy couch is positioned near a stone hearth stove, providing a focal point. Large windows and glass doors allow natural light and outdoor views to enhance the ambiance.

Cottage in Manchester

5 out of 5 average rating, 22 reviews

Tucked Away, cozy space and an easy walk to town

Tucked Away is a newly renovated two-bedroom cottage with all the charm of old Vermont and outfitted with modern touches to make your stay as luxurious as possible. Set in downtown Manchester, Tucked Away is set back off the main road, giving it a more private feel. There is space in a shared driveway for two cars to park, and the house is walkable to almost anything you could want to access in Manchester.

Guest favorite

The historic two-story house features a blue exterior complemented by a white porch adorned with hanging flower baskets. A pathway lined with greenery leads to the entrance, enhancing the inviting appearance of the home surrounded by mature trees.

Guest suite in Dorset

4.89 out of 5 average rating, 180 reviews

Guest Suite in historic 1804 tavern, w/ Breakfast.

You'll have the whole 3rd floor to yourself with a new private bath, large bedroom with a/c, and a separate sitting room/library. Stay in an historic gem, listed on the National Register of Historic Places. Historically sensitive restoration has been done. You'll have a continental breakfast in the house's original dining room. We're a four a minute drive from the center of historic Dorset village.