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In Town Wolfeboro Cottage Caretakers Vacation Home - Near Lake Winnipesaukee

Bedrooms 5
Half Baths1
Property type house
Minimum Stay 2 - 7 nights

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Half Baths
Minimum Stay
2 - 7 nights


Wolfeboro House Rental Photos and Description

5 Bedrooms, 2 Bathrooms, Walk & Bike to all, Oldest Summer Resort in America

Return to Simplicity - Drop your keys in the drawer and walk or bike to everything for the rest of this stress free vacation. This Victorian Home was formerly the Caretakers Quarters for the 9 Quaint Cottages located behind it (which are rented separately and may be available if you need more space for additional family members...See our Website at It is a 3-10 minute walk to most all your vacation needs.

Every age is entertained while walking to ice cream parlors, small boutique stores, waterfront shops, shows, & activities. We have free loaner Bikes & Kayaks. there are 3 free broad sand public beaches and 3 free boat launches on 3 lakes within 5 minutes … activities for every age without having to get back into your car!

Wolfeboro has that Norman Rockwell ambiance. a quintessential small town with the activities, amenities and ambiance that you would hope for. It has a great schedule of free events, (concerts, craft shows, carnivals, sidewalk days, fishing derbies, fairs, book signings, antique boat shows and races, canoeing, kayaking and sailing races, etc.). There is also a brand new hospital, diverse shopping and conveniences to service your needs.

When the Berry's first opened in 1938, it was 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, entertainments and shopping in the village, and returned to their cottages for socializing and well-earned sleep at night.

Boaters Paradise: Boating: For our Boaters... NH requires all drivers of boats and water vehicles to have a license. Multiple Marinas are just a short distance away for boat rentals or service. Free Public Boat Launches are just 5 minutes away to get on Crecent Lake, Wentworth, or Winnipesaukee) Recreational trips abound with many private calm water coves or boat to an evening dinner engagement on the lake. 36 miles in Length and over 100 miles of shoreline, 365 Islands, depths to 350 feet and fishing derbys year-round. Sailing adventurists love the winds of the broads and regattas throughout the summer.

Spectacular Golfing: Golf: Lake Winnipesaukee Golf Club, LLC New Durham NH 03855 is an Exclusive private golf club named one of the top ten new private courses in America by Golf Digest. Full service clubhouse, golf shop and practice facilities. Limited memberships and outings available. Kingswood Golf Club, Inc. Wolfeboro NH 03894 is a 19 hole championship semi-private golf club open to the public. Call for tee times. Restaurant, driving range, practice area, fully stocked pro-shop. Dan Botelho, PGA Lessons. Ridgewood Country Club Moultonboro, NH 03254 is a semiprivate course located in the heart of the Lakes Region. Offering: complete pro-shop, rentals available; cars/carts/clubs, driving range, putting green & the Overlook Tavern. Where you are always welcome!

Norman Rockwell Country Summer: Outdoor Free Concerts in the Park, Summerstock Theater, Town Hall Clock Tower Chimes, Church Bells, Craft and Country Fairs, Free Parks and Fields, Playgrounds, Tennis Courts, Golfing, Sipping a beer on the waterfront, Old Fashion Ice Cream Vendors, Walks along antique Waterways, Waterfalls by the old millway, Idle chat with the locals, Breakfast in the Wolfeboro Diner, Antique Boat Shows, Village Shops... so many pure and refreshing simple pleasures. Come and take it easy for a while.

Make new memories: swimming, fishing, boating, art, food, culture, entertainment, shopping

The Cottages are close to

• Beaches, boat launches and marinas

• Galleries and Restaurants

• Bike trails and Hiking paths

• Shopping, Theater and Music Festivals

• Museums: New Hampshire Wooden Boat , World War II Wright, Libby Natural History

And within an hour’s drive of

• The White Mountains

• Outlet shopping

• Atlantic coast beaches

• Railroad stations and airports

Please go to to book or for pictures, rates, availability and floorplans for all 9 of our cottages in the back.

More Details
  • Events Allowed
  • Minimum Age Limit for Renters
  • children welcome
  • pets not allowed

Property Manager
David De Jager, Owner
Member since: 2008
Speaks: english, spanish
Response time:
Within a few hours
Response rate:
Calendar last updated:
November 28, 2016
Call Manager

About David De Jager, Owner

We are blessed with 4 amazing young inquisitive children and the privilege of living in this GORGEOUS area with so many natural and healthy activities and surroundings. 40 years of local experience give us the insight for nuances not normally offered to visiting guests.

David De Jager, Owner purchased this house in 2008

Why David De Jager, Owner chose Lake Winnipesaukee Area

This is one of the last surviving Cottage Clusters in the area. We have just added the Main House to the availability which can host up to 12 people. This used to be the predominant method of travel for thousands of weary city dwellers escaping the heat, noise and smoke of the summer to arrive by train, carriage and boat to these shores. Most other colonies have been dismantled or sold for condominiums, but we endeavor to preserve this pure and healthy traditional form of family vacations dating back to the 1920's when travel was just a little bit edgy and vacation was in it's advent. Come experience a nostalgic piece of history and see if you don't agree with so many others who feel they have re-discovered something forgotten deep inside them.

What makes this house unique

Having lived here over 40 years, I can help you plan Hiking, Biking, Water Skiing, Scuba, Sailing, Windsurfing, Skin Diving, Hiking, Caving, Free Concerts in the Park, Summerstock Theater, Town Hall Clock Tower Chimes, Church Bells, Craft and Country Fairs, Free Parks and Fields, Playgrounds, Tennis Courts, Golfing, Sipping a beer on the waterfront, Old Fashion Ice Cream Vendors, Walks along antique Waterways, Waterfalls by the old millway, Idle chat with the locals, Breakfast in the Wolfeboro Diner, Antique Boat Shows, Village Shops… SO much more depending on what you can pack in… Please have a look at our reviews which have shown these sentiments.


In Town Wolfeboro Cottage Caretakers Vacation Home - Near Lake Winnipesaukee
average rating of 4.5 based on 2 reviews

The property is amazing. Home away from home!

  • 4 of 5

I would highly recommend the Cottages at Wolfeboro. The owners go out of their way to provide a wonderful experience. When we were in need of another high chair, they provided it immediately. They brought games to the house because they thought we would enjoy the family entertainment. The house is clean and homey and it provided a very relaxed atmosphere for our family. There were 18 of us in the main house and it never felt crowded. The activities in Wolfeboro our endless. We did rock/trail climbing, boating, skiing, tubing, paddle boarding, jet skiing, played at the beautiful state parks and beaches and the list goes on and on. Another thing we loved about staying in the Main house were the wonderful families we met that stayed on the property in the cottages. The overall experience was wonderful.

  • Submitted: Aug 10, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
Owner's Response: Thank you so much for your kind remarks... we love our families who come to get away from the Techno laden world and re-connect in a location that has preserved the benefits of ages past... with a focus on nature, exercise, group enjoyment and interaction that builds lasting family identity. This drives us to service and we are so glad that came through... I hope we can have you back again soon. Sincerely, Dave & Wendy
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Great house, wonderful location & amazing hosts!

  • 5 of 5

We had a wonderful stay in the Caretakers House. It is so conveniently located – walking distance to downtown Wolfeboro, the bike/ walking trail, stores, and more. The house was great with plenty of room to spread out and it is beautifully furnished and exceptionally stocked with everything you might need! There were so many lovely touches from the fresh flowers to the sweet welcome note on the chalkboard. The managers of the property were so friendly and had tons of great suggestions for things to do, places to go, etc. And the kids LOVED the tire swing and their giant top-floor room with the balcony! A perfect place for a family trip! We only wish we could have stayed longer!

  • Submitted: Aug 21, 2015
  • Stayed: Aug 2015
  • Source: HomeAway
Owner's Response: Jenn, thank you so much for your kind review. We have gotten such encouraging words form all of our guests and are excited to see what memories are build for family and friend groups who come to stay in this unique location. People tell us this has been a unique setting so different than hotels or motels of today. They say this is the perfect setting to build connections which are shut out by todays world of indoor life. So often, we go to work and come home, close the front door or garage door and never have that communal experience of knowing those around us like the communities our grandparents spoke of before computers, television, and electronic games. People naturally create an intimate "neighborhood" while visiting each other’s "homes", then sharing meals, walks to various activities around town, to waterfalls, lakes, beaches or events, shops, restaurants and pubs around town and on the Harborfront. 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. I believe you will really love it here with everything within walking distance. If you are considering coming back again next year, don’t forget to click the Boating, Hiking, Fishing, Dining and other links at the bottom of our HomePage at to see a wide variety of Activities, Attractions and Events for kids, singles, couples and the adventurer in you. Let me know if I can encourage you to come again next year. Thank you, Dave
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Nearest Airport
50 Miles
MHT Manchester, NH
Nearest Barpub
0.2 Miles
Short 5 minute walk
Nearest Ferry
45 Miles
Portsmouth Harbor
Nearest Golf
0.5 Miles
Nearest Train
35 Miles
Dover Amtrak
Nearest Motorway
0.1 Miles
Route 28
Nearest Restaurant
0.2 Miles
Short 5 minute walk
Nearest Ski
25 Miles
Nearest Beach
0.2 Miles
Car: necessary

Wolfeboro is a lovely historic quaint New England communities located at the eastern end of Lake Winnipesaukee providing astounding summertime activities including a power boating, sailing, snorkeling/diving, tubing, hiking, water/snow skiing, swimming, fishing, horseback riding, biking, motorcycle touring, flying, touring, and many others. The area also has lots of craft shows, antique fairs, summer stock theater and country fairs throughout the summer. It is a 5 minute walk to Wolfeboro Village for shopping, a 25 minute ride to Laconia for water parks and other children activities, and a 45 minute ride to Meredith. You can walk to the docks to take the Mount Washington Cruise Boat from Wolfeboro Bay to any other part of the lake (Center Harbor, Laconia, Alton, Meredith) or 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.


Rates & Availability

Wolfeboro House Rental Rates

Rental Basis:
per property
Manager accepts payment in:
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Rate Period Nightly Weekend Night Weekly Monthly Event
Early Winter 2016
Nov 27 2016 - Dec 15 2016
2 night minimum stay
Christmas 2016
Dec 16 2016 - Dec 25 2016
Changeover Day: Wednesday
5 night minimum stay
New Years 2016
Dec 26 2016 - Jan 2 2017
Changeover Day: Thursday
4 night minimum stay
Winter 2016
Jan 3 2017 - Apr 20 2017
2 night minimum stay
Early Spring 2017
Apr 21 2017 - May 25 2017
2 night minimum stay
Spring 2017
May 26 2017 - Jun 22 2017
3 night minimum stay
Summer 2017
Jun 23 2017 - Sep 3 2017
Changeover Day: Saturday
7 night minimum stay
My Standard Rate
7 night minimum stay

Additional information about rental rates

Linens&Towels (Optional) $149 + Tax
Cleaning Off Season $199 + Tax
Tax Rate 9.0%

If booking prior to December 1st, we can break payments into 25% due on booking, 25% due in January, 50% due 60 days before arrival. June to September cleaning fee is $299.

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.
Enter dates for accurate pricing
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Available arrival
Available stay (no arrival)


Wolfeboro House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 2320 sq. ft.
Location Type:
  • Downtown ...
  • Lakefront ...
  • Mountain View ...
  • Resort ...
  • Rural ...
  • Ski-Out ...
  • Village ...
  • Waterfront ...
  • Family
  • Historic
  • Sports & Activities
  • Tourist Attractions
  • Clothes Dryer ...
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Living Room
  • Parking
  • Washing Machine ...
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items ...
  • Refrigerator
  • Stove
  • Toaster
  • Child's Highchair
  • Dining
  • Dining Area
  • seating for 12 people
  • 2 Bathrooms
  • 1 Half Bath
  • Bathroom 3 Kids Floor - toilet
    Bathroom 2 Adults Floor - toilet , combination tub/shower
    Bathroom 1 First Floor - toilet , shower
  • 5 Bedrooms, Sleeps 16
  • Master Bedroom Upstairs - 1 king , 1 baby crib
    Master Bedroom Downstairs - 1 queen
    Bunk & Game Room top floor - 4 twin/ single
    Guest Bedroom Upstairs - 2 queen
    First Floor Bedroom - 1 double
  • Ping Pong Table
  • Satellite / Cable
  • Television
  • Bicycles
  • Deck / Patio
  • Golf
  • Kayak / Canoe
  • Outdoor Grill
  • Ski & Snowboard
  • Tennis
  • 4 bicycles
  • Events Allowed
  • Minimum Age Limit for Renters ...
  • children welcome ...
  • pets not allowed
  • bay/sound
  • caves
  • churches
  • cinemas
  • coin laundry
  • festivals
  • library
  • live theater
  • marina
  • museums
  • playground
  • pond
  • recreation center
  • restaurants
  • water parks
  • waterfalls
Leisure Activities:
  • antiquing
  • bird watching
  • eco tourism
  • horseback riding
  • outlet shopping
  • photography
  • scenic drives
  • sight seeing
  • sledding
  • walking
  • whale watching
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • equestrian events
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • hiking
  • hunting
  • ice skating
  • jet skiing
  • mountain biking
  • mountain climbing
  • mountaineering
  • pier fishing
  • rafting
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • skiing
  • snorkeling
  • sound/bay fishing
  • spelunking
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • whitewater rafting
  • wind-surfing
eautifully quaint accommodations, set in a gorgeous country village where you can walk to all the 'Norman Rockwell' type activities you can imagine. Parks, Lakes, Streams, Public Tennis Courts, Little League Fields, Playgrounds, Broad Sand Beaches, Fireworks, Boating of all sorts, Ice Cream Parlors, Antique Boat Rides, Village Shops, Boutiques, Outdoor concerts and plays, country fairs and craft shows, SO MUCH MORE to fill your senses. You will want to be out exploring all the time from this location. Best part is, you will probably park your car and not get back into it for the whole time you are here because everything is so close.

Learn more about this vacation rental at the manager's website:

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