Not every week on this lake needs to be a nine-bedroom estate. These are the small ones: 8 cottages sleeping 4 to 6, with porches, screen doors, and in most cases a dock of their own. 4 of them you can walk into Wolfeboro from.
Winnipesaukee has become a lake of large houses, and we manage plenty of them. But a lot of people are not looking for that. They want a porch, a dock, somewhere to put the coffee down, and no more house than they will actually use.
2 to 3 bedrooms, sleeping 4 to 6. Everyone ends up in the same room, which is usually the point. Nobody is wandering three floors looking for where the others went, and one person can cook while the rest are still on the dock.
4 of these are a walk from downtown Wolfeboro, so you can park the car on Saturday and leave it there all week. That is rarer than it sounds. The lots near the village are small, which is exactly why the cottages are there and the big houses are out on the necks and points.
Several are the original 1940s summer cottages, updated inside but never knocked down for something bigger, which is getting rare here. 4 have a screened porch, which is where most of the week actually happens. They are properly kept but they are summer cottages rather than showpieces, which is exactly what makes them easy to settle into with a young family.
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.
Over 1,000 feet of shoreline on a private 5.7-acre island point, with a sandy beach and panoramic Winnipesaukee views.
2 bedrooms · 2 baths · sleeps 6 · 2 dock slips
South exposure · Sandy beach
Steps to downtown Wolfeboro from this bayfront condo - neverending sunshine, a private deck and dock
3 bedrooms · 3 baths · sleeps 6 · 1 dock slip
Southwest exposure · Perched beach
Under 5 min to town
Renovated cottage on Crescent Lake, short stroll to downtown and the rail trail
3 bedrooms · 1 baths · sleeps 6 · 1 dock slip
East exposure · Off dock · natural shoreline
Under 5 min to town
Freshly renovated top to bottom, with a private yard, a finished game room, and town beaches and boat launches minutes away
2 bedrooms · 2 baths · sleeps 6
None exposure
10-15 min to town
Vintage 1940s character, sandy water entrance, and a swim raft on quiet Crescent Lake, minutes from downtown Wolfeboro.
2 bedrooms · 1 baths · sleeps 4
Southwest exposure · Sandy beach
Under 5 min to town
An updated lakeside cottage that kept its charm, with morning sun on the screened porch and a private dock.
3 bedrooms · 1.5 baths · sleeps 6 · 2 dock slips
East exposure · Off dock · Natural shoreline
Under 5 min to town
A classic 1940s cottage with 200 feet of private shoreline, all-day sun, and views of 20 Mile Bay and Gunstock Mountain.
2 bedrooms · 1.5 baths · sleeps 5 · 2 dock slips
Southwest exposure · Off dock
10-15 min to town
A cozy vintage cottage on the sunset side of Winter Harbor, with golden afternoon light and a deep-water dock.
2 bedrooms · 1 baths · sleeps 4 · 2 dock slips
West exposure · Off dock
The cottages sit on more than one body of water, and for a small group the choice matters more than it does for a big house. One puts you on the main lake with the boats. The other is a quiet pond behind Wolfeboro where the loudest thing is a paddle.
5 cottages
The main lake: 72 square miles, 253 islands, and open water. Best if you are bringing a boat or want to be able to run into town by water.
About Lake Winnipesaukee2 cottages
A small, quiet lake tucked behind Wolfeboro. No big-boat traffic, warmer water than the Broads, and you can walk or bike into town. Best if you plan to swim, paddle, and read on a porch.
About Crescent LakeBy town: Wolfeboro rentals · Tuftonboro rentals
The big houses on this lake are often gone by late winter, sometimes to the same families year after year. The cottages are not. They tend to hold open weeks well into the spring, and often into the summer itself, which means if you are reading this in April there is very likely still a week for you.
The edges of the season also happen to be the loveliest part of it. Late June gets you warm afternoons with half the boat traffic, and September on Winnipesaukee is the month locals take: the water holds its summer temperature well into it, the restaurants in Wolfeboro have tables again, and the light on the water is better than it is in July. A small cottage suits those weeks especially well, when you want the porch and the woodsmoke more than you want the swimming. 6 of these have a porch to sit out on or a fire to sit by.
Summer weeks run Saturday to Saturday. If you want a shorter stay, that is the off-season, September through May, when we rent these same homes with flexible dates and shorter minimums.
Booking sites quote a nightly rate and add the rest at the end. We would rather show you the whole thing now. Here is a real week at one of the cottages, itemized, with nothing left off.
Wolfeboro · Sleeps 4 · 2 bedrooms · Private dock
A refundable $1,000 security deposit is held separately and returned after your stay. It is not part of the rental total.
See Keewaydin CottageEvery week is priced on its own. 3 of these cottages fall to $2,000 in June and September, up to $2,000 off the summer week.
No booking fee and no service fee. We manage these homes ourselves for the families who own them, so there is no listing site taking a cut of your week. What you see above is the number, and we put it in writing before you commit.
Size, not standard. These are the 8 smallest homes we manage, sleeping 4 to 6. Several are the original summer cottages on this lake, built in the 1940s and kept up rather than knocked down and replaced with something bigger, which is getting rare here. Others have been renovated top to bottom, and one sits on its own island point. What they share is scale: two or three bedrooms, often a single bathroom, and in 4 cases a screened porch where most of the week actually happens. They are comfortable and well kept rather than grand, and they are managed by the same office, to the same standard, as the large houses.
Most of them. 6 of the 8 are directly on the water, and the rest are a short walk or drive from a town beach and a public boat launch. 6 have their own dock, so if you are trailering a boat up you can tie it at the house. Tell us the length when you inquire and we will confirm the slip will take it. The rest reach the water off a sandy beach or a perched beach. If swimming straight off the lawn matters more to you than a dock, say so when you inquire and we will point you at the right one.
It is what these homes are best at. A couple, a couple with a child, or two couples sharing all fit here comfortably, and you get a whole house rather than a room: your own kitchen, your own porch, and in most cases your own frontage on the lake. A small group in a large house tends to settle into one corner of it anyway. In a cottage everyone is in the same room, which is usually what people came for.
Yes. 4 of the 8 cottages are an easy walk from downtown Wolfeboro, which means dinner, the bookshop, the ice cream window, and the town docks without ever getting back in the car. In July that is worth more than it sounds, because parking downtown is scarce and you will not have to think about it once. It is also the kind of place where the children can walk in for an ice cream on their own. That is harder to find on this lake than people expect: the lots close to the village are small, so the large houses are almost all out on the necks and points, several miles from a restaurant. If walking into town matters to you, say so when you inquire and we will steer you to the right ones. Wolfeboro calls itself the oldest summer resort in America, and it is a genuinely good town to be able to stroll into on a summer evening.
Peak summer weeks in our cottage collection run $2,000 to $5,500 per week, for the entire house rather than a room. At the low end, a full week works out to $2,550 all in once cleaning, the administrative fee, and state tax are added, which is about $364 a night for the whole cottage. Every week is priced on its own, and 3 cottages drop to $2,000 in June and September, up to $2,000 off the summer week. The cleaning fee varies by house; the administrative fee and the state rooms and meals tax do not. A refundable security deposit is held separately and is not part of the rental total. There is no booking or service fee, because we manage these homes ourselves, and we put the full number in writing before you commit to anything.
Usually yes, and that is the real advantage of the smaller homes. The large houses are often fully booked by late winter, sometimes to the same families year after year, but the cottages tend to hold open weeks much later into the spring, including weeks in July and August. June and September are the quietest to book and the least expensive to rent, and on this lake they are genuinely good weeks: the water is still warm through September and the town is calmer. Send us your dates and we will tell you honestly what is left rather than making you hunt through a calendar.
Not in summer. From late June through August, rentals on Lake Winnipesaukee run Saturday to Saturday, in full weeks, which is what lets the cleaning crews turn a house over properly between guests. Check-in is Saturday afternoon and check-out is the following Saturday morning. If you want a shorter stay, look at the off-season instead: from September through May we rent these same homes with flexible dates and shorter minimums.
They sit in Wolfeboro and Tuftonboro, on Lake Winnipesaukee and Crescent Lake. The ones on Crescent Lake are worth understanding as their own thing: it is a small, quiet lake just behind Wolfeboro, with no big-boat traffic and warmer water than the Broads, and you can walk or bike into town from it. People who want to swim, paddle, and read on a porch usually end up happier there than they would on the big lake. The Winnipesaukee cottages put you on the main lake with the boat access and the open water that comes with it. We will tell you which fits how you actually plan to spend the week.
Sometimes. None of our homes are blanket pet-friendly, but one cottage in this collection will consider a well-behaved dog on a case-by-case basis, with the owner's approval and a pet fee. Ask us before you book rather than after, and tell us the breed, the size, and whether the dog has stayed in a rental before.
We have been arranging summers on this lake since 1940, and we manage these cottages directly for the families who own them. Booking direct means no listing-site service fee, which on a smaller rental is a meaningful share of what you would otherwise pay. It also means a person answers the phone. If the water heater quits on a Tuesday, you are calling an office in Wolfeboro that knows the house and can get someone there, not a support queue in another time zone.
Still deciding? Read our full rental FAQ or look over the rental policies before you inquire.
A cottage week is mostly the porch, the water, and walking into town for dinner. For everything in between, these are the pages our guests actually use.
An interactive map of the places we send guests, from lobster rolls to swimming holes.
Concerts, farmers markets, and fireworks across the Lakes Region.
Where to rent a kayak or a pontoon for the week, and where to put your own in.
The lake itself: 72 square miles, 253 islands, and where the good water is.
It happens, usually once one set of grandparents hears about it. We manage homes all the way up to eighteen, so if the plan grows, tell us and we will move you rather than making you start over.
There is no instant-book button here. Send us your dates and how many you are bringing, and a person in our Wolfeboro office will tell you honestly what is open and what it will cost, all in.