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VRBO is part of the HomeAway family, the world leader in vacation rentals with over 950,000 listings. We offer the largest selection of properties for any travel occasion and every budget. We’re committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together. Learn More

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This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation

Cheshire Travel Tips

Enjoy Cheshire Vacation Rentals

Staying in the Berkshires is a great place to spend your vacation. Cheshire vacation rentals present great opportunities for individuals, groups of friends or the entire family. Cheshire beach homes are just one of the options to choose from with the Berkshires lodging; you can also choose from places such as apartments and cottages that suit your liking. The quaint environment surrounding Cheshire vacation rentals allows for fun and romance as well as fresh air. Some lodging options even welcome your family pets to stay with you on vacation.

Fun in the Berkshires

Whitney's Farm Market and Garden Center, located in Cheshire, is fun for everyone. Depending on the season you visit, you may find a corn maze, Christmas trees or the petting zoo. You can always find lunch at the deli or bakery. Cheshire is known for its cheese making. In 1801, every farmer in Cheshire used one curd of his own cheese to create an enormous cheese for President Jefferson. The cheese weighed over 1,000 pounds and is remembered by a monument standing in Leland Park. Hoosac Lake is open during the summer months for picnicking, and boating is available at Horn's Beach. During the winter, skiing is available at Jiminy Peak, located only eight miles outside of Cheshire.

Cheshire Vacation Rentals Are Right For You

Whether you are looking for a quiet, relaxing getaway, some powder runs on the ski slopes or some historic culture, Cheshire vacation rentals will meet your desires. Cheshire vacation rentals are much cozier than staying in a hotel and will help give you that home away from home feeling. Surrounded by lakes, mountains and other gorgeous scenery, simply walking or driving around Cheshire is sure to lift your spirits. Cheshire is the perfect place for you to stay in to get away from the hustle and bustle of every day life.

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