Vacation Rentals By Owner In Wolfeboro, NH

A storied cabin overlooking Winter Harbor, this 3-bedroom home is the quintessential place to spend your days at the lake. A screened-in porch overlooks gorgeous views of Lake Winnipesaukee and the surrounding woods, alongside a sloped backyard, porch, and dock that are bathed daily in light thanks to their southwest exposure. brThe interior of this cabin is a step back in time, with a great brick fireplace bringing everyone together in the living room and adjoining kitchen. The kitchen is fully equipped. A full bed and two rooms with pairs of twin beds ensure enough room for the whole family.

Cabin

Solitude on Winter Harbor

Wolfeboro, New Hampshire, United States

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Exceptional(18)

$627.09

This house is NOT listed on Craigslist. brbrExclusive - Sunset Point - Lake Wentworth home with generous dock and expansive lawn. Enjoy a quiet morning by the lake away from it all as you live just steps from the lake shore. Vivid unobstructed sunsets abound.brbrThis classic lake home faces west with stunning views of Lake Wentworth and the mountains beyond. The spectacular lakeside setting is the perfect place for swimming, canoeing, kayaking, fishing, and all sorts of water activities. Relax on the swim raft, or head out on your boat to enjoy the lake. Pontoon boat rentals from Melvin Village Marine - book early. Fishing on Wentworth is a favorite pastime and the lake is known for its Smallmouth Bass. Bring your boat and come right up to the generous dock. Included in the rental is use of the kayaks and there is a fishing boat and paddle board available for rent.brbrThe main home has three bedrooms and a loft. The master hosts a queen bed, with en suite master bath with a heated floor, while and the second large bedroom has a queen bed and a full bed. The third bedroom has two queen beds and a full bed in the loft which is great for kids. There are 6 separate beds in 3.5 sleeping areas and rentals are limited to 10 guests. brbrHoneymoon Hall: An additional bedroom with Ethan Allen queen bed and full bed with basic bathroom and shower allows for 2-4 extra guests for a maximum of 12 total. Private deck and beautiful french doors look out to the lawn and the lake beyond. A cute place to get away from the chaos of vacation.brbrFor larger groups - An additional 2 bedroom house for 6 people may be available and booked on VRBO as listing #3082890 or by contacting the owner with this listing. Maximum 18 guests. brbrThe kitchen is fully equipped with a stove, double oven, microwave, generously sized refrigerator, cookware, and utensils. There is also a gas grill on the porch. The oversized glass sliders and bay window provide wonderful views from the great room and the large enclosed porch connects you with the outdoors with added seating for big dinner gatherings. brbrA wood stove set in the fireplace helps set the mood for relaxation and country living on a cool night, but fast cable internet and WIFI are available for your evening enjoyment. A fire pit is available by the lake for you to sit in the evening and cook S'mores and if you happen to have a cloudy day, a 65 inch QLED TV is there for your enjoyment. brbrOptional: Paddle Boards, sunfish sailboat, fishing boat brbrThe lake itself is about five by three miles with many islands and a nature preserve, Stamp Act Island, in the middle. It is known for its tranquility and the superb water quality, perfect for a peaceful vacation. Just a few minutes from downtown Wolfeboro, the house is close to shopping, fine dining and casual restaurants, golf, walking/hiking trails, museums, and all the activities provided by Lake Winnipesauke and the Lakes Region, yet away from the noise and crowds of the bigger lake.brbrKeywords: Cottage, Lake Wentworth, Beach, Wentworth, privacy, family friendly, Lake Winnipesaukee Area, Wolfeboro, Best Lot on the Lake.

Lake Wentworth Estate: Unobstructed Sunset Views, Private Beach, Fire Pit, Lawn

Wolfeboro, New Hampshire, United States

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Exceptional(6)

$284.27

Quiet 2 bedroom, open living cottage. One queen size bed and 2 twin size beds. Just two miles from Center of Wolfeboro, close to restaurants and shops. The circle drive makes it easy, if towing a boat. Public boat launch 1 mile away. Nice sun porch looks out into the woods. Modern kitchen with breakfast bar. Dining table seats eight. Early check in can be accommodated most of the time. Cable/WiFi provided. Smart TV however no cable. This is a roku

Cottage

Quaint Cottage, Closse To Center Of Wolfeboro

Wolfeboro, New Hampshire, United States

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Bath

Sleeps

Exceptional(2)

$343.59

Our 3000 sq. Ft renovated, rustic loft barn is located on 68 private acres, yet 2.5 miles to town. It sleeps 5, 4 single beds in the loft and 1 queen bed in the bedroom. It has a full kitchen, bathroom with a shower, bar, pool table and 65 inch TV. A perfect place to hangout with friends. Minimum age of primary renter is 25 years old. MAX 5 guests. No parties. The barn is on our property, we are in the house should you need anything, otherwise it is private.

Rustic Loft Barn that sleeps 5, close to downtown Wolfeboro

Wolfeboro, New Hampshire, United States

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Sleeps

Exceptional(35)

$540.69

Unwind and make lasting memories at this serene Crescent Lake escape, nestled on a sparkling, one-mile lake with kayak access to the stunning Lake Wentworth. This property offers something for everyone: float in the lake, lounge on the dock, or find your perfect spot in the sun or shade. A charming fishing jetty, a cozy hideaway hammock, and a grassy yard perfect for lawn games and BBQs add to the outdoor fun.brbrThe HomebrbrMaster Bedroom: Queen-sized bed with breathtaking lakefront views.brSecond Bedroom: Twin bunk beds for the kids or young at heart.brThird Bedroom: Two twin beds convertible to a king, also with serene lakefront views.brbrNewly added deck features panoramic lake views, inviting seating, and a dining table for eight—perfect for alfresco meals or evening cocktails. Plus, a covered patio beneath the deck lets you savor the fresh air and lake views, rain or shine.brbrThe main floor boasts an open-concept kitchen, dining, and living area, plus a tranquil sunroom. The lower level offers a family room, a convenient half-bath, and a full walkout slider to a patio leading to the lake—ideal as a private suite or extra living space.brbrExplore the AreabrTake a scenic 1.5-mile stroll along the Cotton Valley Rail Trail, which leads you directly to Wolfeboro’s town docks, shops, and restaurants on Lake Winnipesaukee. From waterfront dining to boutique shopping, there’s something for everyone.brbrAs day turns to night, enjoy stunning sunsets over the lake and gaze at star-filled skies—perfect for photographers and stargazers alike.brbrBook your Wolfeboro getaway and discover the perfect blend of relaxation and adventure at Crescent Lake!

Lakefront Family Retreat in Wolfeboro

Wolfeboro, New Hampshire, United States

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$607.6

**WINTER SPECIAL** Stay Friday and Saturday and Sunday night is free on non-holiday weekends. brbrOften described as Wolfeboro's favorite house, this historic Victorian sits right downtown Wolfeboro and on the water looking across to the town docks, Brewster Academy and Wolfeboro Bay. This two-story unit, occupying the second and third floors, has a beautiful porch overlooking the bay and is located by the famous Yum Yum Shop. Experience the best of both downtown Wolfeboro and Lake Winnipesaukee within steps of your front door.

Condo

Elegant condo on the water in downtown Wolfeboro, right behind the Yum Yum Shop!

Wolfeboro, New Hampshire, United States

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Exceptional(54)

$498.02

Classic 1940's 2 bedroom, well kept, lakefront cottage on Lake Winnipesaukee, with a brand new 3-piece bathroom. Fall is the dream season here-warm water, fiery foliage, golden sunsets, and loons calling at dusk.Enjoy sunrise coffee on the porch or deep water dock. Also included a fire pit, grill, and cozy wood-burning fieldstone fireplace.brbrWolfeboro stays lively with museums, fine dining, concerts, and boat rentals, along with day trips to view fall foliage.brbrThree-night minimum. Peaceful, colorful, romantic. No pets.

Cottage

Lake Winnipesaukee classic fall retreat featured by Yankee Magazine.

Wolfeboro, New Hampshire, United States

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Bath

Sleeps

Exceptional(38)

$310.61

Get away to our cozy lakeside retreat on Rust Pond in Wolfeboro, New Hampshire. Located on the property of a six-acre private residence, this spot is friendly and secluded with woods and water around you. This open-space loft features a bedroom with queen-sized bed as well as a daybed, a living area, a small dining area overlooking the water, a fully equipped galley kitchen and bath with tub and shower. Enjoy the view of Copplecrown Mountain and brilliant sunrises from the waterside or in the gazebo. Rust Pond, a small lake, offers many of the conveniences of the big lakes such as swimming, boating and waterskiing but with far less crowds and noise. This property is bordered by a brook complete with a wooden footbridge. A gravel road runs around the lake perimeter for long walks and mountain hiking, and there are also many forest trails to explore.

Cozy Lakeside Retreat

Wolfeboro, New Hampshire, United States

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$404.62

Enjoy this comfortable knotty pine cottage tucked neatly inside the edge of the forest. This two-bedroom gem gives you a little more privacy yet still offers great views of the lake and is only a short walk to the beautiful sandy beach and community dock area. Bring your own boat or we’ll help you rent one. For a small additionalfee, we offer one of our convenient docks next to the beach. Spend some time on our new swim raft or spend some quiet time fishing off the dock. Piping Rock offers free use of our kayaks and canoes or you can bring the kids over to our playground. Enjoy basketball, volleyball or badminton as well. All on the crystal clear waters of majestic Lake Winnipesaukee in America’s oldest summer resort, Wolfeboro.

Cottage 5--Piping Rock Resort

Wolfeboro, New Hampshire, United States

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Bath

Sleeps

$145.72

Piping Rock Resort located in Wolfeboro New Hampshire, known as the “Oldest Summer Resort in America”. It is a resort with cozy cabins and motel, situated on the shores of Lake Winnipesaukee, a 44,000 acres lake in the heart of the Lakes Region. The motel units are efficiencies; offering fully equipped kitchenettes, A/C, cable TV, and free Wi-Fi. The resort offers kayaks, canoes, basketball hoop, horseshoes, volleyball net, and a playground, not to mention the great sandy beach that is gradual in its entry to the lake. This second level room has a screened in porch and nice amenities. Dock space is available upon request.

Efficiency 5--Piping Rock Resort

Wolfeboro, New Hampshire, United States

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Bath

Sleeps

$582.55

Beautiful knotty pine cottage located right on the shore Lake Winnipesaukee. This location is fantastic offering great privacy yet only a few steps to the community docks and a few more to the beautiful sandy beach that offers a nice gradual entry to the lake. Spend some time on our swim raft or make use of our free kayaks and canoes. Spend some quiet time fishing off the shore or from the docks or let the kids play on our beautiful playground. For a small additional fee we offer dock rental so bring your boat or let us help with a rental. All of this is waiting for you on the majestic crystal clear spring-fed waters of Lake Winnipesaukee.

Cottage 9--Piping Rock Resort

Wolfeboro, New Hampshire, United States

Bed

Bath

Sleeps

Exceptional(2)

$166.1

Piping Rock Resort located in Wolfeboro New Hampshire, known as the “Oldest Summer Resort in America”. It is a resort with cozy cabins and motel, situated on the shores of Lake Winnipesaukee, a 44,000 acres lake in the heart of the Lakes Region. The resort offers kayaks, canoes, basketball hoop, volleyball net, and a playground, not to mention the great sandy beach that is gradual in itsbrentry to the lake. With its close proximity to the lake and beach, a beautiful big and green back lawn, and a great grilling space (large gas grill included), this condo is a perfect Lake Winnipesaukee getaway.There is no air conditioning, or kitchen appliances.

Efficiency 9 --Piping Rock Resort

Wolfeboro, New Hampshire, United States

Bed

Bath

Sleeps

$298.58

Piping Rock Resort located in Wolfeboro New Hampshire, known as the “Oldest Summer Resort in America”. It is a resort with cozy cabins and motel, situated on the shores of Lake Winnipesaukee, a 44,000 acres lake in the heart of the Lakes Region. The motel units are efficiencies; offering fully equipped kitchenettes, A/C, cable TV, free Wi-Fi, upper level screened in porches, and private patio terraces on the lower level. The resort offers kayaks, canoes, basketball hoop, horseshoes, volleyball net, and a playground, not to mention the great sandy beach that is gradual in its entry to the lake. This first-floor room offers a nice covered patio area and nice amenities. Dock space is available upon request.

Efficiency 4--Piping Rock Resort

Wolfeboro, New Hampshire, United States

Bed

Bath

Sleeps

$244.12

Piping Rock Resort located in Wolfeboro New Hampshire, known as the “Oldest Summer Resort in America”. It is a resort with cozy cabins and motel, situated on the shores of Lake Winnipesaukee, a 44,000 acres lake in the heart of the Lakes Region. The motel units are efficiencies; offering fully equipped kitchenettes, A/C, cable TV, free Wi-Fi, upper level screened in porches, and private patio terraces on the lower level. The resort offers kayaks, canoes, basketball hoop, horseshoes, volleyball net, and a playground, not to mention the great sandy beach that is gradual in its entry to the lake. This first-floor room offers a nice patio area and nice amenities. Dock space is available upon request.

Efficiency 3--Piping Rock Resort

Wolfeboro, New Hampshire, United States

Bed

Bath

Sleeps

$255.99

Piping Rock Resort located in Wolfeboro New Hampshire, known as the “Oldest Summer Resort in America”. It is a resort with cozy cabins and motel, situated on the shores of Lake Winnipesaukee, a 44,000 acres lake in the heart of the Lakes Region. The motel units are efficiencies; offering fully equipped kitchenettes, A/C, cable TV, free Wi-Fi, upper level screened in porches, and private patio terraces on the lower level. The resort offers kayaks, canoes, basketball hoop, horseshoes, volleyball net, and a playground, not to mention the great sandy beach that is gradual in its entry to the lake. This first floor room offers a nice patio area and nice amenities. Dock space is available upon request.

Efficiency 2--Piping Rock Resort

Wolfeboro, New Hampshire, United States

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Bath

Sleeps

$499.64

Enjoy one of Piping Rock’s crowned jewels. This two-bedroom suite sits with its toes in the water. Two private bathrooms await your visit along with all the amenities you would find in your ownhomes, such as newly renovated kitchen and bathrooms. This cottage offers air conditioning and ceiling fans in every room. A large living room features a gas fireplace and huge screened in porch. Steps away from our community dock slips you can rent for an additional fee. A few more steps to our pristine sandy beach, with a gradual egress to the crystal clear spring fed waters of Lake Winnipesaukee. Free use of our kayaks and canoes. Let the kids play on our beautiful playground. Volleyball, basketball, and badminton are available as well so enjoy!

Cottage 8--Piping Rock Resort

Wolfeboro, New Hampshire, United States

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Bath

Sleeps

$397.66

Enjoy this beautiful cabin located close to the beach offering fantastic unobstructed views of the lake. Spend your days on our pristine sandy beach, which offers a nice gradual entry into the crystal clear spring fed waters of Lake Winnipesaukee. Take full advantage of Piping Rock’s amenities, which include free use of our kayaks and canoes, playground and volleyball, badminton and basketball hoop. Lounge on our new swim raft or spend some quiet time fishing off the docks. For a small additionalfee, you can rent one of our community docks and enjoy your own boat or let us help you rent one. Enjoy downtown Wolfeboro, the oldest summer resort in America.

Cottage 10--Piping Rock Resort

Wolfeboro, New Hampshire, United States

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Bath

Sleeps

$406.83

Step back in time with this rustic knotty pine cottage located right on the lake. This location is fantastic offering great privacy yet only a few steps to the community docks and a few more to the beautiful sandy beach that offers a nice gradual entry to the lake. Spend some time on our new swim raft or make use of our free kayaks and canoes. Spend some quiet time fishing off the shore or from the docks or let the kids play on our beautiful playground. For a small additional fee we offer dock rental so bring your boat or let us help with a rental. All of this is waiting for you on the majestic crystal clear spring-fed waters of Lake Winnipesaukee.

Cottage 6--Piping Rock Resort

Wolfeboro, New Hampshire, United States

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Bath

Sleeps

$485.13