Vacation rentals in Pownal

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Top-rated vacation rentals in Pownal

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Guest favorite

A vintage tractor is parked on a gravel driveway, surrounded by patches of greenery. In the background, a historic white house with a front porch is visible, framed by tall trees that are bare of leaves, typical of early spring.

Apartment in Pownal

"The Parlors"

This beautiful, spacious, and historic property was formerly the Inn at Oak Hill. It is convenient to Williams College, Williamstown Theater Festival, Clark Art Museum, MassMOCA, FreshGrass Festival, BerkshireStock, Jiminy Peak, Bennington College, VAST snowmobile system and many other destinations in southern Vermont and western Massachusetts. Comfortably furnished with modern amenities such as Wi-Fi and satellite TV, our home also surrounds you with beautifully preserved & original features.

4.95 out of 5 average rating, 149 reviews

Top guest favorite

A post & beam cabin is presented amid a lush forest setting, featuring a wrap-around deck that extends outwards. Tall trees frame the structure, and a gravel path leads to the entrance, inviting guests into a peaceful retreat surrounded by greenery.

Cabin in Bennington

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.

4.96 out of 5 average rating, 100 reviews

Guest favorite

The unique dome-shaped structure is composed of iron and cement, surrounded by lush greenery. Large windows create a bright and airy atmosphere, while the greenhouse-style addition at the front enhances the connection to nature.

Dome in Bennington

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

4.93 out of 5 average rating, 137 reviews

Top guest favorite

An aerial view captures the spacious villa surrounded by vibrant autumn foliage and rolling hills. The property features a pool nestled among trees, with expansive lawns and a gravel driveway leading up to the home, offering a serene retreat in nature.

Villa in Pownal

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!

4.95 out of 5 average rating, 99 reviews

Top guest favorite

A welcoming entryway features a soft, light-colored bench with yellow accent pillows. Wide plank wooden floors run throughout, and a potted plant adds a touch of greenery. The space is illuminated by a pendant light hanging from the ceiling, with stairs visible in the background.

Home in Bennington

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.

4.98 out of 5 average rating, 62 reviews

Superhost

Home in Bennington

Cozy Mountain Retreat - Museums, Trails & Colleges

Perched on the side of Mt. Anthony, this peaceful treehouse-like retreat offers seasonal sunsets with direct access to miles of scenic hiking trails. Relax on 800+ sq. ft. of wraparound decking, grill, dine outdoors, stargaze, or sip your morning coffee surrounded by nature. Just minutes from downtown Bennington, restaurants, colleges, theaters, and local attractions. It’s the perfect escape for hiking, leaf-peeping, or simply unwinding in Vermont’s beautiful Green Mountains.

5.0 out of 5 average rating, 6 reviews

Top guest favorite

Home in Pownal

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.

4.99 out of 5 average rating, 76 reviews

Guest favorite

A colorful mural depicts a serene farm scene. Horses and cows are shown grazing, while a pond features two figures fishing. The farmhouse is surrounded by lush greenery, with people engaged in various activities, showcasing the harmonious life of the countryside.

Home in Pownal

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.

4.85 out of 5 average rating, 92 reviews

Top guest favorite

A living area features a stone fireplace with a roaring fire, surrounded by large windows that invite natural light. A circular coffee table rests on a textured rug, while comfortable seating options include an upholstered chair and wooden accent chairs, complemented by soft lighting.

Cottage in Bennington

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).

4.98 out of 5 average rating, 123 reviews

Top guest favorite

A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.

Home in Bennington

The Vermont Farmhouse|Hiking|Dog Trails|Village

The Luxury of Slowing Down — Vermont Style. Leave the rush behind and feel rested, reconnected and renewed at our dog-friendly, beautifully restored 1860s farmhouse. Wide-plank floors, sun-filled rooms and modern comforts create a warm, impeccably clean retreat. Walk across the road into 280 acres of peaceful Mile Around Woods trails, or stroll into historic North Bennington for cafés and shops. It's all right at your doorstep.

5.0 out of 5 average rating, 135 reviews

Top guest favorite

Two wooden chairs are positioned on a grassy area, facing a gently sloping hill. A modern white farmhouse is visible alongside a deck with stairs. In the background, trees frame the serene landscape, and mountains are faintly visible under a cloudy sky.

Apartment in Bennington

Scenic Vermont Studio

This beautiful retreat is halfway between the ski slopes of southern Vermont and the cultural centers of Williamstown and North Adams, MA. The residence is a modern, spacious, basement apartment, part of an 1860 farm house. It has its own private entrance around the back of the house at ground level. Solar garden lights and motion detector lighting will illuminate your path to the apartment.

4.92 out of 5 average rating, 202 reviews

Guest favorite

Aerial view capturing a modern farmhouse cabin surrounded by vibrant autumn foliage. The landscape features a mix of lush trees in shades of orange, yellow, and green, with distant mountains visible under a clear blue sky. A dirt road borders the property.

Home in Pownal

Modern Farmhouse Retreat

Escape to the serene beauty of Vermont, and indulge in a stay at our modern farmhouse cabin—a perfect blend of rustic charm and contemporary elegance. Nestled amidst the mountains of Vermont, this tranquil retreat offers the ideal getaway for those looking to unwind and explore. Located 10 minutes from Williamstown, museums like WCMA, the Clark, and MASS MOCA are right at your fingertips!

4.89 out of 5 average rating, 47 reviews