Look Beyond Lake Winnipesaukee for Activities in Wolfeboro


Although Wolfeboro is most notable for its location along the shores of Lake Winnipesaukee, this picture perfect village offers plenty of opportunities for adventure beyond the Big Lake.


Even if your Wolfeboro vacation rental rests directly on Lake Winnipesaukee, you might be hard pressed to spend your entire trip participating in popular water sports such as boating, fishing, jet skiing, and water skiing. Therefore, it is important to spread your wings and journey off the beaten path if you want to experience an all-around amazing getaway with hardly a dull moment in sight.


Hiking and exploring are two prerequisites for the ultimate vacation in Wolfeboro, so be sure to bring your adventurous side to life with a quick jaunt to the top of Abenaki Tower for views Lake Winnipesaukee and the Ossipee Mountains. And afterwards, you might be warmed up for the demanding treks along the Cotton Valley Trail or at the Castle in the Clouds in Moultonborough.


After these challenging excursions, you can rest your legs with a ride aboard the M/S Mount Washington, Lake Winnipesaukee’s premier vessel for enjoying the scenic and natural beauty of New Hampshire. With departures directly from Wolfeboro complete with stops in Weirs Beach, there is no better way to catch all the best sights and visit the shops and arcades of this popular town all in one day.


Other great activities to add to your itinerary include shopping along the historic Main Street and golfing on the 18-hole championship course at the Kingswood Golf Club. In addition, Wentworth State Park, which rests along the banks of Wentworth Lake, is an excellent waterfront alternative if you want swimming, hiking, and fishing all in one convenient location.

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Vacation Rentals in Wolfeboro

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Relaxed Style - Incredible Value - Available Year Round - Dogs Welcome – Property 137764

  • Wolfeboro rental - house, 2 bedrooms, sleeps 6, 1 bathroom, lake, village, accept credit card
  • $1,025 - $1,125/week
  • Calendar Last Updated On: Oct 10, 2008
Maximize your vacation budget with this year round home rental. You don't have to be on the water to enjoy all that Wolfeboro has to offer.

Private Year-Round Lakefront Chalet – Property 114814

  • Wolfeboro rental - chalet, 4 bedrooms, sleeps 8, 1 bathroom, 1 half bath, lake, waterfront, washing machine
  • $950 - $1,600/week
  • Calendar Last Updated On: Oct 3, 2008
This lovely year-round chalet is situated in the Lakes Region of New Hampshire- only 20 ft. from waterfront on crystal clear Rust Pond, a quiet 210 acre pristine...

Wolfeboro, NH-Waterfront-Year Round Family Fun-Sleeps 12-14 – Property 160019

  • Wolfeboro rental - house, 4 bedrooms, sleeps 12, 2 bathrooms, 1 half bath, lake, waterfront, accept credit card
  • $1,050 - $2,000/week
  • Calendar Last Updated On: Sep 30, 2008
Welcome to the “Oldest Summer Resort in America” Enjoy this beautiful waterfront property on Sergeants Lake. We are just 4 miles from downtown Wolfeboro and Lake...

A perfect get away Cottage in Wolfeboro, Dogs Welcome – Property 129474

  • Wolfeboro rental - cottage, 2 bedrooms, sleeps 5, 1 bathroom, lake, resort, accept credit card
  • $750 - $900/week
  • Calendar Last Updated On: Sep 21, 2008
Year round Cozy cottage located in Wolfeboro provides a private setting to relax and enjoy all the amenities of the Lakes Region.

5 Bedroom Lakefront Cottage in Wolfeboro NH on Winnipesaukee - Dogs/Kids Welcome – Property 206241

  • Wolfeboro rental - lodge, 5 bedrooms, sleeps 9, 1 bathroom, lake, waterfront, washing machine
  • $1,000 - $2,000/week
  • Calendar Last Updated On: Sep 25, 2008
Whip-Poor-Will-Lodge has been in my family for 100 years, resting on 600 feet of lakefront on Lake Winnipesaukee's South Wolfeboro Bay with a private dock and stairs...

Romantic or Family Summer/Fall Retreat-Featured in Yankee Magazine – Property 119654

  • Wolfeboro rental - cottage, 3 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, lake, waterfront, washing machine
  • $1,500 - $2,600/week
  • Calendar Last Updated On: Sep 16, 2008
This charming cottage with whimsical decor has beautiful lake and mountain views. Lake Wentworth is a quiet 3000 acre lake known for its crystal clear water, sandy...

Classic lakefront home with spectacular water views and gorgeous sunsets – Property 182011

  • Wolfeboro rental - house, 4 bedrooms, sleeps 12, 1 bathroom, 1 half bath, lake, waterfront, washing machine
  • $2,000 - $3,500/week
  • Calendar Last Updated On: Sep 11, 2008
Our classic Lake Winnipesaukee lakefront house located in historic Wolfeboro, New Hampshire has been in our family for over 56 years, and is one of the first...

Quiet and Private Summer/ Fall Cottage on Rust Pond – Property 103045

  • Wolfeboro rental - cottage, 2 bedrooms, sleeps 6, 1 bathroom, lake, town, washing machine
  • $1,100/week
  • Calendar Last Updated On: Sep 6, 2008
Cottage is on a private road with 3.11 acres and 250 ft of water frontage that includes a sandy beach. Cottage cannot be seen from the road or by its neighbors.

Wolfeboro, NH - island home rental with spectacular views-Boat Required – Property 172992

  • Wolfeboro rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, lake, resort, washing machine
  • $1,900/week
  • Calendar Last Updated On: Aug 24, 2008
Welcome to Wolfeboro: 'The oldest Summer resort in America'!! Enjoy all kinds of water sports at this island home with private sandy beach, breakwater dock, with 28...

Fun Family Wolfeboro Village Waterfront Cottage on the bay – Property 156254

  • Wolfeboro rental - cottage, 3 bedrooms, sleeps 8, 1 bathroom, 1 half bath, lake, waterfront, washing machine
  • $995 - $2,295/week
  • Calendar Last Updated On: Aug 18, 2008
Charming Wolfeboro waterfront cottage in the heart of antique boat land. In the summer watch the gorgeous wooden boats cruise by or the Wolfeboro water ski team...

Charming water front home on Lake Winnipesaukee, Wolfboro NH – Property 194898

  • Wolfeboro rental - house, 3 bedrooms, sleeps 11, 2 bathrooms, lake, village, washing machine
  • $1,200/week
  • Calendar Last Updated On: Aug 13, 2008
Beautiful cottage located on Lake Winnipesaukee in winter harbor. 100 ft of Sandy beach with gradual shallow entry - great for young children.

Newly renovated vacation getaway on pristine lake; – Property 124941

  • Wolfeboro rental - house, 3 bedrooms, sleeps 8, 1 bathroom, lake, tennis, tennis court
  • Calendar Last Updated On: Jul 24, 2008
Newly renovated vacation home is not like those other places you've rented before. Brand new kitchen, bath, interior walls, new flooring, new furniture and new...

Lake Winnipesaukee Old Mill Post & Beam 4 Bedroom House – Property 192235

  • Wolfeboro rental - lodge, 4 bedrooms, sleeps 10, 3 bathrooms, 1 half bath, lake, waterfront, washing machine
  • $3,500 - $5,500/week
  • Calendar Last Updated On: Jul 7, 2008
Peaceful Expansive Views and Water lapping at your shore! Echoing Loon calls nightly. Spectacular Unique 5000 sq.ft. home re-crafted from an Old Post and Beam Mill.

Cozy Island Getaway! Wolfeboro Sleeps 6 - Boat required to access – Property 155090

  • Wolfeboro rental - cottage, 3 bedrooms, sleeps 6, 1 bathroom, lake, waterfront, washing machine
  • $1,850/week
  • Calendar Last Updated On: Jun 17, 2008
Hurry! Summer weeks are going fast ! Enjoy island living with all of the comforts of home in this cozy, updated cottage located on Barndoor Island on beautiful...

Brand New Adirondack Lake House-Gorgeous Water! – Property 130163

  • Wolfeboro rental - cottage, 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, lake, resort, tennis
  • Calendar Last Updated On: Jun 6, 2008
Beautiful Adirondack style, year round 3 bedroom, 2 1/2 bath, waterfront home on Crescent Lake in the 'Oldest Summer Resort in America.' One-acre lot with gently...

Home on 4 Acres & 138' Sandy Beach Frontage – Property 107810

  • Wolfeboro rental - house, 3 bedrooms, sleeps 7, 1 bathroom, lake, waterfront, washing machine
  • Calendar Last Updated On: Mar 12, 2008
This property is a short 5 miles to downtown Wolfeboro. Wolfeboro is a quaint village billed as 'The Oldest Summer Resort in America'.

Enjoy Your Very Own Private Island - – Property 128734

  • Wolfeboro rental - estate, 8 bedrooms, sleeps 32, 5 bathrooms, 1 half bath, lake, waterfront, washing machine
  • Calendar Last Updated On: Mar 1, 2008
Parker Island is a 2.7 acre private unbridged island located just outside of Wolfeboro Bay. Unmatched views of the “Broads” and 360 degree views of the lake.

Beautiful Waterfront Family Compound with 325 Feet of Lake Frontage – Property 313991

  • Wolfeboro rental - house, 13 bedrooms, sleeps 32, 4 bathrooms, 2 half baths, air-conditioning, washing machine
  • Calendar Last Updated On: Dec 16, 2007
Laughing Loon, our wonderful family compound is located in Wolfeboro, New Hampshire and is available for rental for the first time in 50 years.
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