Vacation rentals with breakfast in Bennington County

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Top-rated breakfast rentals in Bennington County

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Guest favorite

Autumn foliage lines the banks of the Metawee River, showcasing vibrant reds, oranges, and yellows. Sunlight filters through the trees, reflecting off the water's surface. A carpet of fallen leaves adds color to the tranquil setting, creating a peaceful natural atmosphere.

Home in Dorset

5 out of 5 average rating, 12 reviews

The Lower Hollow House, dip into river in backyard

Beautiful home in Dorset perched on the Metawee River 12 min to Bromley or Manchester Village, 9 min to the Dorset Horse Show. This 3500 square ft. home has all your needs covered. Smart tech, 2 fireplaces, 5 TV's, streaming+cable entertainment, vaulted living room ceiling, dining room w/ large table, sun room, fully equipped kitchen, 3 private acres, sun deck, walking trails. Left side has main kitchen, 3 bedrooms & two bathrooms. Right side has two bedrooms, livingroom, 1 bath & a kitchenette.

Top guest favorite

A cozy bedroom features a spacious bed adorned with a floral quilt. Soft light filters through the window, casting gentle shadows on the bed. Two bedside tables with lamps flank the bed, and framed art pieces are displayed on the walls.

Private room in Bennington

5 out of 5 average rating, 127 reviews

E and E’s B and B Queen Bed Rm+ Pool & Hot Tub

We are located on 16 East Street in Bennington VT minutes from rt 7 and route 9 Main Street. Summer is more like a mini resort with a beautiful in-ground pool and Hot Tub. We also feature plenty of in-room USB phone plug-ins and extensions, in room TVs.. Perfect for couples or bring a child. Sunning Deck or shaded patio dining or just relaxing with a good book poolside or the indoor lounge with a drink. We’ve got you covered. Many unexpected amenities. Longer stays allowed for professionals.

The exterior of the guest house is framed by vibrant autumn foliage, showcasing shades of orange and yellow. A small lawn area is visible in front, with two red chairs positioned beside decorative planters. The front entrance features multiple black-paneled doors, evoking a rustic charm.

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

Top guest favorite

A charming townhouse is set amidst vibrant autumn foliage, showcasing a classic exterior with a gabled roof and large windows. The surrounding trees display a mix of red, orange, and green leaves, creating a picturesque environment that highlights the seasonal beauty.

Townhouse in Dover

4.98 out of 5 average rating, 61 reviews

See Vermont burst into a blaze of color right here

Trade city noise for mountain air. Our end‑unit townhouse sleeps eight in three true bedrooms (4 beds, 3 full baths) and puts you five minutes from Mount Snow, a short walk to Green Mountain National Forest trailheads, and ten minutes to Lake Whitingham. Shop, golf, ride horses, hunt antiques, or do absolutely nothing—everything you came to Vermont for is right here. A romantic escape, a family adventure, a restful retreat the Lemondrop lodge is for you. Early check-in and late checkout

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

The exterior of the historic Henry House features white clapboard siding and black shutters, framed by tall trees. A welcoming porch is furnished with rocking chairs, while American flags add a patriotic touch. Well-maintained gardens surround the entrance, enhancing the home's classic charm.

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 spacious living area features wooden beams and an inviting layout. Comfortable seating includes a green sofa and soft neutral armchairs surrounding a wooden coffee table. Bright patterned decor complements the vibrant green kitchen cabinetry visible in the background.

Home in Winhall

5 out of 5 average rating, 24 reviews

Summer in Winhall - Fire-pit, Hot Tub, Sleeps 8

3 Bedroom, 3 Bathroom Sleeps 8 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

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.

Top guest favorite

The exterior of a two-bedroom cottage is shown, featuring a blue-grey facade and shrubs surrounding the entrance. A gravel driveway leads to the house, which is set back from the main road, offering a sense of privacy among the greenery.

Cottage in Manchester

5 out of 5 average rating, 28 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

4.9 out of 5 average rating, 188 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.

Top guest favorite

A white farmhouse-style structure is set on a lush green hill, surrounded by a clear blue sky. The building features a gabled roof, multiple windows, and a small cupola. A neat lawn frames the house, emphasizing its inviting exterior.

Home in Bennington

4.98 out of 5 average rating, 305 reviews

Cozy Modern Sugar House with spectacular views.

This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.

Top guest favorite

The exterior features a two-level home with a front porch adorned with seating. A vibrant garden filled with colorful flowers and greenery surrounds the entrance. Decorative elements, such as hanging planters and garden lights, complement the serene landscape.

Apartment in Pownal

4.95 out of 5 average rating, 202 reviews

The Shepherd's Retreat

This in-law apartment is on the first floor of our 2 level home and has its own separate entrances. It features an open floor plan with galley kitchen and breakfast bar. This location has a peaceful relaxing atmosphere but with easy access to shopping, site seeing, hiking, and is minutes away from historic Bennington, Vt and the Berkshires (Mass Moca Museum).