AC/HEAT, FREE WIFI, BIKES, KAYAKS & FIREWOOD  603-569-9999 (call/text)

The Cottages of Wolfeboro

Cabin Rentals -Lake Winnipesaukee Vacation

Cabin & Cottage Rentals Near Lake Winnipesaukee, NH

10 Best Cabin & Vacation Rentals

603 569 9999 Call or Text any Questions to me directly

Original 1938 Advertisement in Boston Papers:



12 Charming Cabin Rentals tucked into the only private woodlands in this Quaint Downtown!  Take the train, Cross the lake, or drive here, but rest assured, you can confidently place your keys in a drawer for the week and stroll to shows, activities, lakes, trails, museums, dining, shopping and SO much more.  There's something for EVERY age in Wolfeboro, the Oldest Summer Resort in America! 

​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.  

Since purchasing the property in 2008, we have worked hard to retain each cottage's nostalgic ambiance while ensuring your comfort.  Our Cottages are freshly decorated, and all modern conveniences and technology tastefully integrated into the setting to optimize and preserve period character.   So book early, park your car and never have to get back in until you choose... Walk to Beaches, Waterfalls, Canals, Fishing Piers, Hiking Trails, Quaint Shops, Restaurants, Conveniences, and Ice Cream Parlors.  We have free loaner bikes and kayaks for your use.

Wolfeboro is a lovely historic quaint New England community located at the eastern end of Lake Winnipesaukee providing a broad variety of  activities including power boating, sailing, snorkeling/diving, tubing, hiking, water skiing, swimming, fishing, horseback riding, biking, motorcycle touring, flying, touring, craft shows, antique fairs, summer stock theater and country fairs... just a 5 minute walk to Wolfeboro Waterfront Village for shopping, a 25 minute ride to Laconia & Wiers Beach for water parks and kids activities, and a 40 minute ride to Meredith. At the town docks, pick up the Mount Washington Cruise Boat from Wolfeboro Bay to 5 ports around the lake (Center Harbor, Laconia, Alton, Meredith), take an antique speedboat ride with Captain Denny in the Millie B, an island cruise to deliver mail on the Sophie C, or just relax in a canoe or kayak in back bay.   Don't miss this opportunity to relax and absorb the 'Golden Pond' Mystique in classic Norman Rockwell style.


​We Host Romantic Getaways for 2 up to Family and Friend Gatherings up to 40 people.  Our prices range from $109 - $269 per night depending on your length of stay, time of year and cottage selection.  All have kitchens or kitchenettes, outdoor grills and picnic tables, and charm.


Have you considered asking anyone else to join you this year?  Everyone tells us that this is the perfect setting to consider inviting other people to join you as we have specifically tailored our design efforts to build connections between you and your friends/family.  We are uniquely set up to accomplish what most other lodgings do not… Group gatherings are some of our MOST satisfied customers because of the fact that people can be together but not on top of one another.  They create an intimate "neighborhood" visiting each other’s "homes" and taking walks to various activities around town, to the waterfalls, the lakes, beaches or fall events around town. 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.  We can host up to 36 people at a time if you get us early enough…  I believe you will really love it here with everything within walking distance.  If you think this might be a good idea, I can take over for you if you want me to send off some information to any of your family or friends, just let me know their email or they can simply call me…

Our History and Offering for our Cabin Rentals