Holiday rentals with breakfast in Bennington County

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.

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

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!

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!

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.

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

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

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 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.