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Lucky Vacation Homes

Wolfeboro, NH

A New Hampshire lake town on the eastern shore of Winnipesaukee, calling itself the oldest summer resort in America since 1768.
Waterfront Wolfeboro Bird House Cottage

Waterfront Wolfeboro Bird House Cottage

4.91 (99)

Wolfeboro, NH

3 bedrooms•3.5 baths

On Winnipesaukee

The Oldest Summer Resort in America

Royal Governor John Wentworth began clearing land here in 1768 for a country estate beside the lake that now carries his name, and Wolfeboro has claimed the title ever since. The town was incorporated in 1770 and grew up at the head of Wolfeboro Bay, on the eastern shore of Lake Winnipesaukee. The lake is the largest in New Hampshire at seventy-two square miles, with 288 miles of shoreline and more than 250 islands scattered across it. Steamboats brought the first summer crowds in the 1850s, the railroad arrived in 1872, and the town has run on roughly the same rhythm ever since.

Why Wolfeboro

Why Wolfeboro

Most of it sits within a few minutes of the town docks, and the rest is a short drive around the lake.

Where to Go in Wolfeboro

Lake Winnipesaukee

The Big Water

Lake Winnipesaukee

Wolfeboro Bay

The Docks

Wolfeboro Bay

Cotton Valley Rail Trail

Twelve Miles

Cotton Valley Rail Trail

Wright Museum of WWII

1939 to 1945

Wright Museum of WWII

New Hampshire Boat Museum

Wooden Hulls

New Hampshire Boat Museum

Mount Washington Cruises

Lake by Ship

Mount Washington Cruises

Millie B Boat Rides

Mahogany

Millie B Boat Rides

Allen Albee Beach

Lake Wentworth

Allen Albee Beach

Clark House Museum

Town History

Clark House Museum

Guest Reviews

What Our Guests Say

4.92

800 reviews

Lucky’s place was just as described. Upon arrival Lucky and Jason greeted me and showed me around the area since I’ve never visited before. This location is great for a little getaway to Ptown. Easy check in/out process! I’ll be booking again in the future. Thank you for your hospitality!

Joseph

Stayed in October 2026

Cozy house with a beautiful lake view.

Nelson

Stayed in October 2026

Stayed a couple days and it was a beautiful spot! Clean cottage and yard. The deck out back is awesome! We enjoyed our stay here and would book again!

Katherine

Stayed in October 2026

We had a very relaxing stay at Lucky's cottage! Everything was as expected! check in and check out went very smooth and Lucky answered all texts quickly!

Sandra

Stayed in October 2026

The Season

When to Come to Wolfeboro

July and August are the peak. The lake warms up, the cruise boats run and downtown fills with families who have been coming for generations. June is quieter and cheaper, with the water still cold enough to notice. Late September into October brings the foliage, and the White Mountains an hour north are worth the drive for it. Winter locks the bay in ice and hands the town back to the people who live here.

Get more when you book direct

Lower prices, every time

Pay less than you would anywhere else. No middlemen or platform fees.

Direct line, real care

Book with the team that actually runs the property. Faster answers, better service, real accountability.

Not just a transaction

We go further for direct guests. We’re building a relationship, not closing a booking.