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Lakefront cottage in autumn on Lake Winnipesaukee

Lake Winnipesaukee · September to May

Off-season at the lake

Fall foliage, skiing, ice fishing, snowshoeing, or a few quiet days by the water.

Weekends welcome
Stay a few nights or settle in longer
Flexible dates
Arrive and leave any day of the week
Priced per stay
Ask for a quote for your dates

Tell us your dates, group size and budget. We'll help you find a home and coordinate with the owner. Not every property is available off-season, and each stay needs the owner's approval.

Ask about a stay

Off-season homes

Browse the homes below, then send us your dates so we can check availability with the owner.

See them all on a map

Showing 5 of 5 homes

Wolfeboro Lake Winnipesaukee waterfront vacation rental — 4BR, sleeps 10
Winter Harbor · Wolfeboro

Sunset Harbor

Lake and mountain views, sunset decks, and a screened porch on Winter Harbor, plus a rec room with foosball for the kids.

  • Southwest sunsets
  • Lake and Mountain views
  • Screened Porch
  • Lower level game room

4 bedrooms · 2.5 baths · sleeps 10 · 2 dock slips

Sleeping
  • 1 Queen on the main floor
  • 1 King en suite on the main floor
  • 2 Fulls (upstairs)
  • 2 Sets of twin bunks (upstairs)
On the water

Southwest exposure · Off dock

Off-season stays from $3,800

Weekends and longer stays welcome. Contact us for a quote for your dates.

Tuftonboro Lake Winnipesaukee waterfront vacation rental — 7BR, sleeps 14
Winter Harbor · Tuftonboro

Winter Harbor Lodge

A contemporary seven-bedroom lodge on Winter Harbor with a private sandy beach, calm water, and en-suite rooms for fourteen.

  • Private sandy beach
  • Ping Pong table
  • 7 bedrooms (4 en suite)

7 bedrooms · 6.5 baths · sleeps 14 · 2 dock slips

Sleeping
  • 1 King (en suite)
  • 1 King
  • 4 Twins, upstairs (en suite)
  • 1 King, upstairs (en suite)
  • 2 Bunks (twin over full)upstairs (en suite)
  • 1 King, lower level
  • 2 Twins, lower level
On the water

South exposure · Sandy beach

10-15 min to town

Off-season stays from $6,400

Weekends and longer stays welcome. Contact us for a quote for your dates.

Wolfeboro Lake Winnipesaukee waterfront vacation rental — 5BR, sleeps 14
Wolfeboro Bay · Wolfeboro

Timberlane

Southwest sunsets, a private sandy perched beach, and a lower-level game room with pool, bar and shuffleboard.

  • Gameroom with pool, shuffleboard, TV and bar
  • Southwest sunset deck
  • Private perched beach
  • Minutes to town

5 bedrooms · 4.5 baths · sleeps 14 · 2 dock slips

Sleeping
  • Queen, main floor (en suite)
  • Queen
  • Queen
  • Queen
On the water

Southwest exposure · Perched beach · Natural shoreline

Under 5 min to town

Contact us for off-season pricing

Weekends and longer stays welcome. Contact us for a quote for your dates.

Tuftonboro Lake Winnipesaukee vacation rental — 2BR, sleeps 6
Off the lake · Tuftonboro

The Neck Cottage

Freshly renovated top to bottom, with a private yard, a finished game room, and town beaches and boat launches minutes away

  • Newly renovated
  • Finished game room
  • Minutes to boat launches and beach

2 bedrooms · 2 baths · sleeps 6

Sleeping
  • 1 King (en suite)
  • Twin Bunks
On the water

None exposure

10-15 min to town

Off-season stays from $1,500

Weekends and longer stays welcome. Contact us for a quote for your dates.

Wolfeboro Crescent Lake waterfront vacation rental — 2BR, sleeps 4
Crescent · Wolfeboro

Crescent Lake Cottage

Vintage 1940s character, sandy water entrance, and a swim raft on quiet Crescent Lake, minutes from downtown Wolfeboro.

  • Walk to town
  • Air conditioned
  • 1940's charm
  • Swim raft and boat mooring

2 bedrooms · 1 baths · sleeps 4

Sleeping
  • 1 Queen
  • 2 Twins
On the water

Southwest exposure · Sandy beach

Under 5 min to town

Off-season stays from $1,400

Weekends and longer stays welcome. Contact us for a quote for your dates.

Let Us Find You a Place

Tell us when you're coming, how many people, and your budget, and we'll match you with the best available property.

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Mailing address (optional) — helps us get your lease and paperwork out faster if you book.

Frequently Asked Questions

Yes. From September through May our rentals work differently from summer: dates are flexible, stays are shorter, and we match you with a home personally rather than through a calendar. 5 of the homes we manage, in Wolfeboro and Tuftonboro, have owners who have said yes to off-season stays in principle, and they are listed on this page.

Yes, weekends and longer stays are welcome, with flexible check-in and check-out days. Off-season homes have a minimum price per stay rather than a fixed minimum number of nights. Tell us the dates you want; we will confirm the length, price and owner approval when arranging your booking.

Each stay is quoted individually, because it is priced per stay rather than as a Saturday-to-Saturday week. Where a starting price is shown on this page, it is the minimum price for the stay, not a nightly or weekly rate. The same minimum may cover different lengths of stay; fewer nights do not necessarily cost less. Contact us for the price and length available for your dates. Beyond the rent there is a cleaning fee that varies by house and New Hampshire's 8.5% rooms and meals tax. You will have the full figure in writing before you commit to anything.

No. Whether a home rents outside the summer is up to its owner, and every off-season stay is approved with the owner case by case. Some of the homes we manage are year-round houses and some are summer places that close up for the winter, so tell us your dates and your group and we will only put forward homes that are open to them. We handle the coordination with the owner; you just show up.

That is a house-by-house question and the owner is the one who knows the answer. When you inquire for winter dates, say what matters to you, whether that is heat, a plowed driveway, a woodstove, or reliable internet, and we will ask the owner and pass along exactly what they tell us before anything is agreed.

More than people expect. Late September and October bring the foliage, with the lake at its calmest and the towns still open. Winter means skiing within a short drive, ice fishing and snowshoeing once the lake freezes, and quiet weekends by a fire. Spring is the quietest season of all, which is exactly why some guests choose it. Our events calendar and local guide on this site cover what is on around the lake in any given month.

Send an inquiry through this page or call the office at (603) 569-1000 with your dates, group size, and budget. We come back with the best available option, confirm it with the owner, and put the lease through DocuSign. Payment is by check to our Wolfeboro office. There is no instant-book button, by design: we arrange every stay personally.

Then you are looking for a long-term stay rather than an off-season one, and it is arranged a little differently: one lease for the duration, pricing negotiated with the owner, and a tax exemption once a stay reaches 185 consecutive days. Our long-term rentals page explains how those come together, and the same office handles both.

Staying a month or longer? See long-term stays, or read the full rental FAQ and rental policies.

The Towns in the Quiet Months

The towns the homes above sit in. Each one keeps going after the summer crowds leave, and each is a different kind of quiet.

What's On Around the Lake

Farmers markets, holiday events, and the restaurants and beaches that stay open after Labor Day. We keep these up all year.

Prefer to call? We're happy to help.

Call (603) 569-1000