Pet-friendly vacation rentals in Bennington County

Mountain side acres

10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

The Farm Cottage- Quiet 1BR on Hobby Farm

Welcome to our peaceful 1-bedroom cottage on a small hobby farm, perfect for couples or solo travelers visiting the Bennington area. This cozy space is designed for rest and simplicity. Whether you're in town visiting family, exploring local trails, or just passing through for a few days, you’ll have a comfortable place to unwind and recharge. Thoughtful touches like fresh eggs from our chickens and homemade jams await you, while the cozy setup makes it easy to settle in and feel at home.

Warm Brook Farm | Farmhouse & Gardens | Hot Tub

Step into the timeless charm of Warm Brook Farm, a beautifully restored 18th-century farmhouse in Southern Vermont. Once a lively inn and stagecoach stop in the early 1800s, this elegant retreat combines historic character with modern luxury. Enjoy a genuine chef's kitchen, award-winning gardens, and upscale amenities throughout. We cover your Airbnb service fees — the price you see is what you pay. An inviting getaway to relax, explore, and create lasting memories with family and friends.

Ski and Play in Manchester Center!

Fully renovated 2000 sf 5 bedroom/2 bathroom house in the heart of Manchester Center, VT! 6 miles to Bromley, 15 miles to Stratton, 6 miles to the Vermont Summer Festival horse show, and less than a mile to all of the shops and restaurants Manchester Center has to offer! You cannot beat this location no matter the season! The house is set back off the road and surrounded by woodlands so even with all of these amenities at your fingertips, you feel like you're far off the beaten path!

MOUNTAIN NEST, views, Manchester, hot tub,

Convenient to downtown Manchester's outlet stores and restaurants,golf (equinox golf course 3 miles away) hiking, kayaking and fishing (battenkill river)skiing-Stratton or Bromley, hot tub on full deck with close-up views of Mount Equinox, these mountain views will either make you weep or sing for joy, dines 8 easy, master on main (king bed). This home was intended to bring INSIDE the natural beauty you see OUTSIDE. Complete with vaulted living area and exposed timber beams throughout!

Quaint One-Story Vermont House with Mountain View

From our quaint one-story house, you can see a variety of scenery, from the bright changing colors of the leaves in the autumn to the soft piles of snow in the winter. Experience the quiet of the nearby woods, and see roaming animals such as deer or turkey. Make sure to stop at one of the nearby lakes, each of which offers a variety of amenities, and lush scenery. In the winter, keep warm in the cozy living room next to the fireplace, while having a chat with your friends and family.

5BR Rustic Mountain Sanctuary Dome Home

Find connection in this secluded mountainous retreat. Enmeshed in the natural landscape, this space is only accessible via unpaved roads. Even the journey here is part of the adventure. *4WD & Snowtires are needed during winter & early spring due to the possibility of snow or mud* This property requires a lot of upkeep and the steward will likely be onsite during your stay, however the whole house will be exclusively reserved for your booking. This space will rejuvenate & inspire

The Vermont Farmhouse|Hiking|Dog Trails|Village

Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

The Equinox Cottage

The Equinox Cottage is a quick 3 minute drive to the Equinox Hotel and the heart of Historic Manchester Village. Enjoy the shops, outlets, restaurants, cafes, golfing, and relaxed summer vibe. The Cottage is also an easy walk to the trails in the Equinox Pond preserve. Enjoy this pristine wilderness oasis, plus hiking up Equinox Mountain and surrounding trail system without having to step into your car. This peaceful, spacious, serene spot is ideal for summer relaxation.

Modern 3-bedroom A-frame in Londonderry w/ Pond

This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min).

White Doe Farm •Lovingly restored antique farmhome

Built circa 1860, our Rupert, VT farmhouse has been fully renovated for modern comfort while still retaining original rustic touches like original hardwood floors, a Rumford fireplace, and an antique wood-burning stove. We'd love to host your next family gathering, romantic getaway, or solo retreat! Minutes to Dorset, and Manchester. Micro-Wedding inquiries welcome!

White Rock Farm

White Rock Farm is a working sheep farm in Bennington VT, part of the scenic and historic Valley of Vermont and surrounded by the Green and Taconic Mountains. The farm is a place where successive generations have been stewards of its 295 acres. First established in 1828, today it remains a working farm that includes livestock, maple syrup, and timber production.