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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

Gloucester - 102 vacation rentals

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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

Gloucester Travel Tips

Gloucester Vacation Rentals Offer Fun, Excitement and a Bit of History

For many of us, taking a vacation means going to a place with gorgeous beaches, great food, good entertainment, and a myriad of sights and activities. Gloucester vacation rentals have all of that, and then some. Gloucester is a town that is both loaded with vacation activities and steeped in unique history. It's the oldest seaport in the United States, and it's also home to America's oldest arts colony. And it's definitely no wonder why—located on Cape Ann, Gloucester is surrounded by the sea and all the bounty and inspiration it holds.

Find Inspiration in Gloucester's Beauty

Gloucester's spectacular landscapes and views have fueled the creative fires of all kinds of artists, from writers (T.S. Eliot, Herman Melville, Rudyard Kipling, and John Updike) to painters (Winslow Homer, Maxfield Parrish, and Edward Hopper) to playwrights and poets (Israel Horowitz, Charles Olson, and Vincent Ferrini). There are numerous festivals, sights, and block parties to get your creative juices flowing all year round, but if you're more interested in action, there's plenty in Gloucester for you as well. Gloucester beach homes are the perfect places from which to go kayaking, swimming, hiking, or sailing. The town is also home to dozens of points of interest, from historical to architectural to cultural. Gloucester has something for everyone to appreciate.

Immerse Yourself in all That Is Gloucester

If you're looking for North Boston lodging near the beach that has an endless array of sights and activities ripe for appreciation, Gloucester vacation rentals are the perfect accommodations for you. You can live like a local while you experience everything the town has to offer, from sports to dining to shopping and entertainment. And when you're done for the day, you can come back to your very own cozy abode and feel truly at home.

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