The finest weeks on Lake Winnipesaukee begin with an extraordinary place to stay.
Our luxury collection brings together exceptional waterfront estates in Wolfeboro, Tuftonboro and Alton, with private sandy beaches, deep-water docks, boathouses, guest houses, expansive lake views and beautifully designed spaces made for gathering.
Every home is personally selected and locally managed by our team in downtown Wolfeboro. We know these properties firsthand, and we'll help you find the one that truly fits your family, whether you're planning a multi-generational summer tradition, a special celebration or simply an unforgettable week on the lake.
Jump straight to any of them below. Save the ones you like to your account, or use Share to send a home to whoever you are travelling with.
Southwest sunsets, a private sandy perched beach, and a lower-level game room with pool, bar, and shuffleboard.
4 bedrooms · 4.5 baths · sleeps 10 · 2 dock slips
Southwest exposure · Perched beach
Under 5 min to town
A gradual walk-in sandy beach and 155 feet of private shoreline on Wolfeboro Bay, with room for fourteen.
5 bedrooms · 5 baths · sleeps 14 · 3 dock slips
Northwest exposure · Sandy beach
5-10 min to town
A grand lake house with west-facing sunsets over Jockey Cove, a game room, a boathouse, and a private dock.
6 bedrooms · 5 baths · sleeps 12 · 2 dock slips · boathouse
West exposure · Off dock
Several private acres on Winter Harbor with a sandy beach, a boathouse with a rooftop deck, and a hidden tunnel down to the water.
6 bedrooms · 5.5 baths · sleeps 14 · 4 dock slips · boathouse
South exposure · Sandy beach · Natural shoreline
10-15 min to town
New construction, private beach, and views that do the talking.
7 bedrooms · 7 baths · sleeps 12 · 2 dock slips · guest house
Southwest exposure · Perched beach · Natural shoreline
10-15 min to town
A contemporary seven-bedroom lodge on Winter Harbor with a private sandy beach, calm water, and en-suite rooms for fourteen.
7 bedrooms · 6.5 baths · sleeps 14 · 2 dock slips
South exposure · Sandy beach
10-15 min to town
A private pickleball court, fire pit, and game room on Winter Harbor, with water views and room for fourteen.
6 bedrooms · 6 baths · sleeps 14 · 2 dock slips · guest house
North exposure · Perched beach
10-15 min to town
A contemporary Winter Harbor home, fresh renovations for 2026, with five en-suite bedrooms and a two-story wraparound deck.
5 bedrooms · 5.5 baths · sleeps 16 · 2 dock slips
North exposure · Off dock
5-10 min to town
A sandy beach and west sunsets off one of the lake's best lots, with gracious single-floor living for the whole group.
5 bedrooms · 3 baths · sleeps 10 · 2 dock slips
West exposure · Sandy beach
This expansive 5-bedroom, 5.5-bath home, plus a charming guest house, welcomes up to 12 guests for an unforgettable escape on the shores of Lake Winnipesaukee.
5 bedrooms · 5.5 baths · sleeps 12 · 2 dock slips · guest house
Northwest exposure · Off dock
A landmark home on Sewall Point with panoramic lake and mountain views, sunset decks, and room for fourteen.
7 bedrooms · 4.5 baths · sleeps 14 · 2 dock slips
Southwest exposure · Off dock
With breathtaking west-facing views and unforgettable sunsets, this spacious retreat features four beautifully appointed bedrooms, including three king suites and a fun bunk room for kids, plus four modern bathrooms and a bright, open-concept living area designed for gathering and relaxation.
4 bedrooms · 5 baths · sleeps 10 · 2 dock slips
West exposure · Sandy beach
A warm, stately lake home on Winter Harbor with west-facing sunsets, a private guest house, and a sandy beach.
5 bedrooms · 4.5 baths · sleeps 10 · 2 dock slips · guest house
West exposure · Sandy beach
Quiet luxury on Sewall Road with expansive waterfrontage, sandy beach, and guest house.
4 bedrooms · 5 baths · sleeps 10 · 2 dock slips · guest house
South exposure · Sandy beach · Sandy beach shoreline
Under 5 min to town
An open, light-filled home on Smith Point with soaring windows over the lake, a master suite balcony, and expansive decks.
4 bedrooms · 4.5 baths · sleeps 10 · 1 dock slip
North exposure · Off dock
20+ min to town
A grand two-house compound with a level grassy waterfront, a sandy beach, and sunsets, steps from downtown Wolfeboro.
8 bedrooms · 9.5 baths · sleeps 14 · 2 dock slips · guest house
Southwest exposure · Sandy beach
Under 5 min to town
We loved working with you and would 100% recommend and use again over Air BNB. Loved the personal service and communication.
You guys have been terrific for many years in helping our family find a vacation rental. Sorry we missed you on Sunday, but since we were so close to town someone always had to go to a store and it was my turn to drive. Thanks for the pie! And as always thanks for accommodating our dogs; we know that can be challenging.
This was the perfect house for our growing family! We had the best 2 weeks, looking forward to next year! Thanks tor the pie, it was a big hit!
They sit on named stretches of the eastern and southern shore: Winter Harbor, Wolfeboro Bay, Broads, Jockey Cove, Pick Point, Sewall Point, and Springfield Point. In town terms that is Wolfeboro, Tuftonboro, and Alton. If you know the lake, those names will tell you more than a map will. If you do not yet, call us and we will talk you through how each one differs on water, wind, and how long it takes to get to town by boat.
Being on the water with its own dock is where we start, not where we finish. What earns a place is any one of the following, done properly: high-end kitchen appliances, en suite bedrooms, a game room, a boathouse, a wide sandy beach, or a large level lawn with spectacular views and the sunset. No house has all of them and none needs to. Size and price are not the test either, and there are bigger and more expensive homes on this lake that are not in this collection. For scale, these run 4 to 8 bedrooms and sleep 10 to 16. 6 have a separate guest house and 2 have a boathouse. We manage all of them directly for the families who own them, which is why you are talking to us and not to a listing platform.
Peak summer weeks in this collection run $12,000 to $25,000 per week. Rates are per week rather than per night, and each week is priced on its own, so June and September weeks come in below the July and August peak. Beyond the weekly rate there is a cleaning fee that varies by house, a $100 administrative fee, and New Hampshire's 8.5% rooms and meals tax. A refundable security deposit is held separately and is not part of the rental total. You will have the full figure in writing before you commit to anything.
That is what most of them are booked for. The collection runs 4 to 8 bedrooms and sleeps 10 to 16. 6 include a separate guest house, which matters when two or three families are sharing a week. When you inquire, tell us how the group breaks down rather than just the headcount: how many couples, how many children, whether anyone needs a bedroom on the main floor. That is what actually determines which house will suit you.
Yes. Every home in this collection is waterfront with its own dock, and most have room for more than one boat. 2 include a boathouse. Dock size and water depth vary by property, so if you are trailering a boat up, tell us its length when you inquire and we will confirm it fits before you book. If you are not bringing one, there are marinas within a short drive of all of these homes that rent by the day or the week.
You talk to a person. Send an inquiry through this site or call the office at (603) 569-1000 and we will confirm what is available, answer questions about the house, and hold the week while you decide. There is no instant-book button here by design: we book every stay personally. A deposit of roughly 50% secures the week and the balance is due before you arrive. Leases are signed electronically through DocuSign, and payment is by check to our Wolfeboro office.
No. Rentals on Lake Winnipesaukee run Saturday to Saturday, in full weeks. Check-in is Saturday afternoon and check-out is the following Saturday morning, which is what gives the cleaning crews time to turn a house this size over properly. Booking two or more consecutive weeks is common, and each week is priced individually when you do.
Yankee Pedlar Realtors has been arranging summers on this lake since 1940, and we manage these homes directly for the families who own them. Booking direct means no listing-site service fee, which at these weekly rates is not a small number. It also means that if something goes wrong mid-week you are calling a Wolfeboro office that knows the house and the owner, not a support queue.
Still deciding? Read our full rental FAQ or look over the rental policies before you inquire.
The collection sits on Winter Harbor, Wolfeboro Bay, Broads, Jockey Cove, Pick Point, Sewall Point, and Springfield Point. If you know Winnipesaukee, those names will tell you more than a map will.
The guides we keep for the rest of the Lakes Region, for when you want to get off the dock.
72 square miles, 274 islands, 183 miles of shoreline, and the history behind it.
Explore the lake
An interactive map of restaurants, beaches, boat launches, and local spots.
Open the map
Concerts, farmers markets, and fireworks across the Lakes Region.
See the calendar
Marinas, public launches, fuel, and moorings around the lake.
Find a marinaYankee Pedlar is a real estate brokerage as well as a rental office. If owning on this shoreline is somewhere in your thinking, the same people who book your week can show you what is for sale on it, and tell you what a house like it earns as a rental.
Luxury rentals book quickly, especially for peak summer weeks. Tell us your dates and how many you are bringing, and we will tell you what is still open.
