Holiday rentals in Pownal

Mount Anthony Cabin

This post & beam cabin is tucked into the forest at the base of Mt. Anthony. Surrounded by woodlands and adjacent to a 300-acre Christmas tree farm, this cozy cabin offers peaceful seclusion while located only 10 minutes from downtown Bennington. Enjoy a meal on the wrap-around deck or drive a few miles into town where you can find local restaurants and breweries. Step outside for numerous hiking and walking opportunities, or explore the historical and cultural sites Bennington has to offer.

"The Chambers"

"The Chambers", formed from the sleeping quarters of the former Inn at Oak Hill, is convenient to Williams College, Williamstown Theatre Festival, Clark Art Museum, MassMOCA, Fresh Grass Festival, Jiminy Peak, Bennington College, BerkshireStock, VAST trails, and many other destinations in southern VT and western MA. Comfortably furnished with amenities such as Wi-Fi and satellite TV, this suite also surrounds you with beautifully preserved and original historic architectural features.

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.

Vermont Vacation Villa—Grapevine Getaway

Nestled in the stunning natural beauty of Vermont, this striking villa offers the perfect escape from the hustle and bustle of everyday life. Surrounded by rolling hills, and picturesque countryside, this home is a paradise. Whether exploring the area's cultural institutions, immersing yourself in the natural beauty of Vermont, or relaxing and unwinding with family and friends, this vacation home is the perfect retreat. Experience the magic of this beautiful area for yourself!

The Old Pine House

Step into a piece of Bennington history with this beautifully renovated historic home, nestled in the heart of downtown. Built in 1830, enjoy the perfect mix of classic elegance and current style in the updated kitchen, renovated bathrooms, and cozy living spaces. With its light-filled rooms, and wide plank floors, this home is full of character and warmth. Just a short walk from local shops, restaurants, a dispensary and brewery, this home offers both convenience and comfort.

Cozy Home in Pownal VT

Tucked away in peaceful Pownal, this 2-bedroom country-style retreat is the perfect escape for couples, families, remote workers, and nature lovers. Enjoy a fully equipped kitchen, washer/dryer, and a spacious outdoor patio for relaxing or dining under the stars. Located just 10 minutes from Williamstown and 20 minutes from Bennington and Mount Greylock, it’s an ideal base for hiking, golfing, skiing, or simply unwinding in the quiet countryside.

Quarry Hill Farm in Pownal, VT

Airbnb service fees included in pricing. Stay at one of the most charming and oldest farmhouses in Pownal. It's secluded, surrounded by natural beauty. Close to the cultural benefits of Bennington and Williamstown. Or you can stay at the farm, take walks, cook local foods, have space and time to relax, read, have great conversation. From Quarry Hill Farm you can explore the region , take in nature and spend time with your guests in privacy.

Cozy, bright 3-bedroom Cottage with fireplace.

Cozy, spacious brook-side cottage with 3 bedrooms, 2 baths, fully-equipped kitchen, fireplace, and serene, 382-acre country setting. Colorful artwork, designer furnishings, and well-appointed kitchen and bathrooms will make you feel welcome and at home. Historic charm of Bennington ten minutes away. NYC (182 miles); Boston (118); Mt. Snow (32); Prospect Mountain (13). Close to MASS MoCA (22), Tanglewood (49) and Manchester outlets (32).

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.

Beautiful, 100 Acre Retreat, Williamstown 10 Mins

Your solar-powered, cozy cottage is nestled in a field of wild flowers with gorgeous mountain views. A hot tub/spa soothes your body after enjoying boundless outdoor adventures. The art and culture of Williamstown are just a 10 minute drive. Indulge your palate with a fully equipped kitchen. Rejuvenate for tomorrow with a warm fire and a blissful, memory-foam slumber.

Brookside Cottage

Drift off to the sound of a babbling brook outside the bay window in this cozy country cottage. Minutes from Downtown Williamstown, North Adams and Bennington, VT. We are about 20 minutes away from Jiminy Peak for downhill skiing. The trails behind our house are ideal for snowshoeing, nordic skiing, and snowman building.