In winter, Massachusetts’ Cape Cod Peninsula is devoid of summer crowds, historic lighthouses are blanketed in snow, and the crabbing season comes to an end. But that doesn’t mean the Cape is closed for business – in fact, the cooler months can be some of the most idyllic to explore, provided you’re bundled up and have a comfortable Airbnb or a Cape Cod vacation rental to relax. And if you’re planning to visit when temperatures hit the 70s in June, you’ll want to start planning your stay already – returning visitors often book their summer homes a year in advance. Here you’ll find some of the best Cape Cod vacation rentals, geographically organized from Upper Cape (towns like Sandwich and Falmouth) to Outer Cape (like beloved Provincetown). Whether you’re traveling with the whole family or visiting on a romantic weekend getaway, there’s a home for everyone on this list and plenty of iconic cedar shingle cottages to visit.
Looking for ideas on what to do on the 110 km long peninsula when you have booked your accommodation? We’ve got a comprehensive guide to Cape Cod that explains where to eat and what to see while you’re there, no matter if you’re staying in Bourne or Brewster.
While we have not stayed at all of the rental properties featured unless otherwise noted, these listings are verified against Superhost status, amenities, location, previous guest reviews, and decor.
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