0 Bedrooms for 1 Guest
Price $10 - $1000+

105 Bennington Holiday Rentals, Houses & Apartments

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Bennington holiday rentals from 7 rental sites including Booking.com, HomeAway, HRS Holidays, and more, ranging from $44 to $3000 a night. 
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    Information about Bennington

    About Bennington

    Nestled into the most southwest corner of Vermont just east of the New York state line and north of the Massachusetts border, Bennington is the epitome of small towns in Vermont. Its history includes the 1777 Battle of Bennington during the Revolutionary War. The downtown area is known for its historically preserved architecture and river walk which parallels the Walloomsac River. It is so known, in fact, that it is nationally recognized by the National Trust for Historic Preservation as a designated “Vermont Main Street”. Vermont has even given the city the nickname of “Vermont’s Most Historic Town”. For a quaint, quintessential Vermont vacation, look no further than Bennington.

    Things to do in Bennington

    Every year in September, the town celebrates one of the most beloved ingredients in the culinary scene: garlic. At the 21st Annual Garlic and Herb Festival this September 3 & 4, 2016, garlic-lovers will enjoy everything from garlic ice cream to garlic braids, and participate in activities for adults and children alike. Kids can bounce on inflatable bounce houses and get their faces painted while adults can relax in the beer and wine garden and listen to live music.

    To experience the beautiful outdoors, explore Woodford State Park. Just a 10-minute drive from Bennington, this 398-acre state park has several hiking trails and a 2.7-mile trail around its main lake. You an even rent kayaks from the park and hop in the lake for a leisurely ride.

    The Bennington Museum is a great stop to make on your vacation. Located on Main Street about a half a mile from the historic downtown, the museum offers guests a taste of Vermont’s art, history and innovation. Notably, the museum houses the largest collection of Grandma Moses paintings in the world. Admission is just $10.

    Finally, if you’re looking for a place to cool off during the stifling heat of the summer months in Vermont, the Dorset Quarry is the place to go. Privately owned by a couple who bought the Quarry in 1997, this natural swimming hole is a crowd pleaser. Visitors come to this spot in the Green Mountain National Forest from all over the area to jump off cliffs into the water while many others lounge on the rocks alongside the water. Don’t forget to take any trash you leave behind, as this has become one of the concerns with the couple who wants to keep it open to the public without having to maintain it entirely by themselves.

    Day Trips from Bennington

    Williamstown, Massachusetts, just a 20-minute drive over the state line to the south, is another quaint small New England town. Williamstown is home to Williams College, which U.S. News & World Report lists as the #1 Liberal Arts College in the country. Just next to the campus of Williams College, the town has hosted the Williamstown Theater Festival every summer since 1955. Enjoy entertainment ranging from live productions of plays written by Tennessee Williams to a Design and Tech Showcase. Downtown Williamstown also offers local restaurants to dine in and pubs to frequent during your stay. All in all, the town is a great day trip from Bennington without having to travel very far.

    Bennington Accommodations

    Vacations rental options from Tripping.com range from large farmhouses with plenty of land for activities and a pool to cool off in to hotel rooms in the heart of historic downtown. Tripping.com has everything you’re looking for in a vacation rental in quaint Bennington, Vermont.

    Stroll along Main Street and you’ll have no trouble finding a place to stop in for a drink or an antique store to browse through. Madison Brewing Company Pub & Restaurant is a great local spot to try some craft beer from Vermont or grab a bite to eat. Stop by Owl’s Nest Upholstery & Antiques to peruse through their assortment of antiques. Whatever your destination, enjoy all the shops and restaurants along the way.

    Transportation in Bennington

    Getting to Bennington from out of the state is best done via a flight to Albany International Airport. From the airport, rent a car and drive just under 1 hour to reach Bennington. Or, fly into Burlington International Airport and drive 2 hours and 45 minutes. There are some shuttles and buses that run to both Albany and Burlington, but a car is the most efficient and reliable way to reach Bennington.

    A public bus system exists in Bennington, but the stops it makes throughout the day are limited so it should be seen as more of a shuttle system. The best way to get around is to walk, taking in the sights and architecture of downtown Bennington. For those places out of reach, a car is best.

    Vacation Rentals in Bennington

    Find the best Bennington vacation rentals with Tripping.com. Choose from 97 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $44 a night to $3000 a night.

    Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 27 of homes in Bennington offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 10 rentals with pool or jacuzzi, or relax with the family in one of the 79 homes with cable TV.

    For all those dog lovers and cat lovers, Bennington offers 19 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

    Search properties from 7 rental sites in Bennington where the top providers in that area are Booking.com, HomeAway, and HRS Holidays. There are 57 Booking.com rentals, 26 HomeAway short term rentals and 7 HRS Holidays vacation rentals.