Vacation rentals with breakfast in Bennington County

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Top-rated breakfast rentals in Bennington County

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

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Guest favorite

Guest suite in Dorset

4.88 out of 5 average rating, 147 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 sitting room/library. Stay in an historic gem, listed on the National Register of Historic Places. Historically sensitive restoration has resulted in beautifully decorated historic home. 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, which has excellent restaurants, a cafe, and a general store.

Sep 19 – 26

G$27,859 GYD per night

Guest favorite

Apartment in Weston

5.0 out of 5 average rating, 22 reviews

Peaceful Woods- Suite with Private Entrance

Our 5 acres are nestled in Vermont woodland bordering the Green Mountain National Forest two miles from the town of picturesque Weston up a well maintained dirt road. We welcome anyone looking for peace and quiet surrounded by both perennial and vegetable gardens and berry patches. Six ski areas both Alpine and Nordic and six golf courses are an easy drive as well as the Weston Playhouse, Weston Priory, The Vermont Country Store, the West River Farmers Market and several amazing restaurants.

May 14 – 21

G$28,334 GYD per night

Superhost

Tiny home in Shaftsbury

4.52 out of 5 average rating, 137 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

Mar 24 – 31

G$24,545 GYD per night

Superhost

Home in Dorset

5.0 out of 5 average rating, 7 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, 3 fireplaces, TV area, streaming 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.

May 28 – Jun 4

G$130,772 GYD per night

Guest favorite

Farm stay in Bennington

4.96 out of 5 average rating, 84 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 .

Aug 8 – 15

G$33,420 GYD per night

Guest favorite

Home in Bennington

4.99 out of 5 average rating, 276 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!

Nov 27 – Dec 4

G$43,917 GYD per night

Guest favorite

Townhouse in Dover

4.98 out of 5 average rating, 41 reviews

Enjoy a dash of luxury & whimsy 5 min from Mt Snow

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.

Jul 22 – 29

G$92,745 GYD per night

Guest favorite

Cabin in Winhall

4.96 out of 5 average rating, 292 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

Aug 19 – 26

G$58,401 GYD per night

Superhost

Home in Manchester

4.81 out of 5 average rating, 48 reviews

Perfect reunion house! Pool, tennis, fireplac, dog

There's room for everyone at The Reunion House! Wood burning fireplace, BBQ. Piano, So big, multiple families can share. Sleep 18. Dogs welcome. Great winter season ski house too! Free outdoor pool, tennis, lawn games on 30-acre estate resort. (shared with other guests) Private indoor heated pool avail for $250/hr. 8 bedrooms • 5 baths • 13 beds • WiFi • Fireplace • BBQ • Firepit • Piano • HUGE lawn • 30-acre resort.

Apr 8 – 15

G$193,961 GYD per night

Guest favorite

Cottage in Manchester

5.0 out of 5 average rating, 9 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.

Jan 19 – 26

G$86,247 GYD per night

Guest favorite

Apartment in Pownal

4.94 out of 5 average rating, 180 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).

May 3 – 10

G$22,703 GYD per night

Guest favorite

Condo in Dover

4.99 out of 5 average rating, 105 reviews

*Mountain Oasis: Base of Mount Snow Retreat*

This charming 1-bedroom, 1.5-bathroom ski condo at the base of Mount Snow ski resort comfortably accommodates 4 guests. The condo boasts a fully stocked kitchen, cozy fireplace, spacious deck, convenient office space, and access to an amenity center which has an outdoor pool, hot tub, sauna and gym. Perfect for short or long term stays.

Sep 22 – 29

G$74,168 GYD per night