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This region encompasses most of southwestern Vermont, including the historic towns of Manchester and Bennington. With both outdoor and cultural opportunities, there is something to satisfy everyone here, from shopping in the Manchester outlet stores and small local stores, to visiting nearby ski resorts such as Bromley, Stratton, Magic Mountain and Mount Snow. Hildene, the Abraham Lincoln family home, is located in Manchester and open to the public year-round. The  annual Manchester Vermont Summer Festival Horse Shows offer six weeks (in July and August) of top equestrain competition.

Covered bridges are prevalent in the area, making for beautiful bike tours in the summer or autumn. Both the Long Trail and the Appalachian Trail traverse the area, and the Battenkill River, home of world-famous trout fishing, flows to the south. Manchester is also home to the Equinox Resort and Spa, which boasts one of the top 75 U.S. golf courses (as rated by Golf Digest), and Riley Rink, which has an Olympic size indoor skating rink in winter and hosts concerts in the summer. Manchester is also home to the Southern Vermont Arts Center, with multiple galleries on a beautiful 407-acre estate. Manchester also hosts the Manchester Music Festival presenting concerts in the spring and summer.

The small city of Bennington is known for the Battle of Bennington that took place nearby at the start of the Revolutionary War. Bennington Potters, a well-known pottery and housewares company, offers interesting shopping. Dorset, next door to Manchester, hosts the renovated Dorset Playhouse, home to the summer Dorset Theater Festival.

Renting a vacation rental in this region allows vacationers the opportunity not only to enjoy Vermont, but to visit tourist attractions in nearby Williamstown, MA and Saratoga Springs, NY, home to the horse racing in the summer.

The region is easily reached from Interstates 87 and 90 near Albany, New York, and from Interstate 91 for those traveling from Boston or Connecticut. There are major airports in Albany and Hartford, CT, as well as Vermont’s own Burlington International Airport.