Whether you're traveling with the whole family or visiting on a romantic couple's weekend, there's a home for everyone on this list-and plenty of iconic cedar shake cottages to go around. Here, you'll find some of the best Cape Cod vacation rentals, organized geographically from the Upper Cape (towns like Sandwich and Falmouth) to the Outer Cape (like beloved Provincetown). And if you're thinking of visiting when temperatures hit the 70s come June, you'll want to start planning your stay already-return visitors often book their summer homes a year in advance. But that doesn't mean the cape is closed for business-in fact, the chillier months can be some of the most idyllic to explore, provided you're adequately bundled up and have a cozy Cape Cod Airbnb or vacation rental to lounge in. Come winter, Massachusetts's Cape Cod peninsula is devoid of summer crowds, historic lighthouses get a dusting of snow, and crabbing season wraps up.
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