About Us, Oldest Summer Resort in America

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About Us

Cottage Rentals near Lake Winnipesaukee, NH

1763 Wolfeboro Vacation is Born

Wolfeboro was chosen by John Wentworth, last colonial governor of New Hampshire, for his summer home which he built on Lake Wentworth in 1763. This gained Wolfeboro the distinction of being "The Oldest Summer Resort in America", cradled between two mountain ranges and contains borders on six different lakes and ponds.

Lake Winnipesaukee

Wolfeboro was chosen by John Wentworth, last colonial governor of New Hampshire, for his summer home which he built on Lake Wentworth in 1763. This gained Wolfeboro the distinction of being "The Oldest Summer Resort in America", cradled between two mountain ranges and contains borders on six different lakes and ponds.

Lake Winnipesaukee is our largest lake, and the 6th largest natural lake entirely in the United States. It is 28 miles long, 13 miles wide and has 274 habitable islands. Winnipesaukee is an Indian term meaning "Smile of the Great Spirit". Wolfeboro is a thriving residential resort town located on Routes 28 and 109 in the heart of the Lakes Region.

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Cabin Rentals near Lake Winnipesaukee, NH

1938 Our Cottages are Born

1763 Wolfeboro Vacation is Born

First opened in 1938, a time when automobile vacations were still new, exciting and just a little bit dangerous. Weary city dwellers could escape hot urban summers and call a little piece of the country the Oldest Summer Resort in America. Couples and Families played horseshoes and tossed balls under tall trees, enjoyed lake pleasures, e

First opened in 1938, a time when automobile vacations were still new, exciting and just a little bit dangerous. Weary city dwellers could escape hot urban summers and call a little piece of the country the Oldest Summer Resort in America. Couples and Families played horseshoes and tossed balls under tall trees, enjoyed lake pleasures, entertainment and shopping in the village or dining on the Harborfront. They would then return to their cottages for socializing and a well-earned peaceful sleep at night.

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2010 Family & Friends Gathering

1763 Wolfeboro Vacation is Born

2010 Family & Friends Gathering

We are tucked into the only private woodlands in this “Norman Rockwellesque” Quaint Downtown!

We offer a unique old-time simple vacation environment with activities for every age in the Oldest Summer Resort in America.

We can host up to 75 people.. Using the cottages as individual households you can create your intimate "neighborhood" wh

We are tucked into the only private woodlands in this “Norman Rockwellesque” Quaint Downtown!

We offer a unique old-time simple vacation environment with activities for every age in the Oldest Summer Resort in America.

We can host up to 75 people.. Using the cottages as individual households you can create your intimate "neighborhood" while visiting each other’s "homes", taking walks to various activities around town, to the waterfalls, the lakes, beaches or events, shops, restaurants, and pubs around town and on the Harbor front. Sitting in one of our bench swings, lounging in hammocks or gathering in the Adirondacks by an evening fire are great community and relationship builders.

And so, Put your keys in a drawer for the week and stroll, bike (FREE) or paddle (FREE KAYAKS) to shows, activities, lakes, trails, museums, dining, shopping and SO much more. There's something for EVERY age in Wolfeboro, in the center of the Lakes Region, on Lake Winnipesaukee and at the base of the Famous White Mountains, as well as an hour drive to experience the New England Coast!

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