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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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, satellite or cable
  • $2,000/week
  • Calendar Last Updated On: Nov 20, 2009
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...

Comfy and Cozy - Private Wooded Setting - Wireless Internet - Dogs Welcome – Property 137764

  • Wolfeboro rental - house, 2 bedrooms, sleeps 6, 1 bathroom, lake, village, pets considered
  • $1,125/week
  • Calendar Last Updated On: Nov 18, 2009
Enjoy all that Wolfeboro has to offer without paying waterfront rental prices. This cottage is located in a private setting. The last house on a dead end street...

Enjoy Your Very Own Private Island - – Property 128734

  • Wolfeboro rental - estate, 8 bedrooms, sleeps 32, 5 bathrooms, 1 half bath, lake, waterfront, garden
  • $10,000 - $15,000/week
  • Calendar Last Updated On: Nov 10, 2009
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.

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

  • Wolfeboro rental - cottage, 2 bedrooms, sleeps 5, 1 bathroom, lake, resort, pets considered
  • $800/week
  • Calendar Last Updated On: Nov 7, 2009
We have a few weeks left for this Fall, book now. Fall colors are spectacular! Year round Cozy cottage located on Wolfeboro Neck that provides a private setting to...

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

  • Wolfeboro rental - cottage, 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, lake, waterfront, garden
  • $1,500 - $2,400/week
  • Calendar Last Updated On: Oct 22, 2009
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...

Private Year-Round Lakefront Chalet – Property 114814

  • Wolfeboro rental - chalet, 4 bedrooms, sleeps 8, 1 bathroom, 1 half bath, lake, waterfront, terrace
  • $500 - $1,200/week
  • Calendar Last Updated On: Oct 16, 2009
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...

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

  • Wolfeboro rental - house, 2 bedrooms, sleeps 7, 1 bathroom, lake, waterfront, garden
  • $1,400 - $1,600/week
  • Calendar Last Updated On: Oct 8, 2009
This property is a short 5 miles to downtown Wolfeboro. Wolfeboro is a quaint village billed as 'The Oldest Summer Resort in America'.

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, garden
  • $995/week
  • Calendar Last Updated On: Oct 6, 2009
Charming Wolfeboro waterfront cottage in the heart of antique boat land - as seen in the Guardian. In the summer watch the gorgeous wooden boats cruise by or the...

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

  • Wolfeboro rental - cottage, 2 bedrooms, sleeps 6, 1 bathroom, lake, town, satellite or cable
  • $1,100/week
  • Calendar Last Updated On: Oct 6, 2009
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.

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, internet access
  • $2,000 - $4,000/week
  • Calendar Last Updated On: Sep 26, 2009
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...

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

  • Wolfeboro rental - lodge, 5 bedrooms, sleeps 8, 1 bathroom, lake, waterfront, balcony
  • $1,500 - $2,250/week
  • Calendar Last Updated On: Sep 21, 2009
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...

Lake Winnipesaukee Waterfront in Unique Downtown Wolfeboro Location – Property 246346

  • Wolfeboro rental - house, 4 bedrooms, sleeps 12, 4 bathrooms, downtown, lake, garden
  • $3,000 - $6,000/week
  • Calendar Last Updated On: Sep 1, 2009
Watch the July 4th Fireworks from your dock! Large and comfortable home within walking distance to groceries, restaurants and shopping.

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

  • Wolfeboro rental - cottage, 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, lake, resort, satellite or cable
  • Calendar Last Updated On: Jul 15, 2009
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...

Lake Winnipesaukee, sleeps 4, w/boat slip for 20' – Property 186753

  • Wolfeboro rental - cottage, 2 bedrooms, sleeps 4, 1 bathroom, lake, resort, balcony
  • Calendar Last Updated On: Jun 17, 2009
This 2-bedroom guest house is located in desirable Winter Harbor. Enjoy beautiful views of the lake and Mt. Belknap from the dock or beach area.

Waterfront, Lake Winnipesaukee, Sleeps 5-6 w/boat slip for 20' – Property 109334

  • Wolfeboro rental - house, 3 bedrooms, sleeps 5, 2 bathrooms, lake, waterfront, balcony
  • Calendar Last Updated On: Jun 17, 2009
This 3-bedroom house is located in desirable Winter Harbor. Enjoy beautiful views of the lake and Mt. Belknap from the dock or beach area.

The Heritage Resort, 4 stars, best beaches & views on Lake Winni. Wolfeboro, NH – Property 241106

  • Wolfeboro rental - lodge, 10 bedrooms, sleeps 24, 6 bathrooms, lake, resort, internet access
  • Calendar Last Updated On: May 6, 2009
The Heritage Resort....where vacations never end because your memories last forever. The feeling of stress evaporating into thin air like smoke rising from a...

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

  • Wolfeboro rental - house, 13 bedrooms, sleeps 32, 4 bathrooms, 2 half baths, garden, terrace
  • Calendar Last Updated On: Dec 29, 2008
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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