Vacation rentals in Cumberland County

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Top-rated vacation rentals in Cumberland County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Rental unit in Portland

Clean & Simple Apt w/Parking-Close to Downtown

Your cute, cozy one bedroom apartment is close to all that Portland has to offer! Your home away from home, you have 400 mbps Wifi, the fastest Portland offers along with a comfortable desk to work from. Centrally located, the space it is a short drive to all of the great restaurants, bars, shops, parks and more! It is close to the 295-N ramp (Freeport outlet shopping is just a few exits down).Our location blends city living with that “just-off-the-beaten-path” feel that offers pleasant rest

$155 per night

SUPERHOST

Rental unit in Windham

Tranquil Waterfront In-Law Apartment

Sarah's in-law apartment is located on Collins Pond in North Windham, 15 miles to Portland. The backyard fire pit is perfect for relaxation and the picnic table overlooking the pond is a beautiful location to enjoy your morning coffee. Take the kayaks out for a morning venture or the canoe out for the gorgeous sunset! Sarah's one bedroom, one bathroom apartment with private entry, private kitchen, private living space and separate parking will make your stay a tranquil one. Come visit!

$129 per night

SUPERHOST

Home in Lisbon

Unplug at a Beachy Bolthole with Classic New England Style

Chill on the porch after exploring a scenic local walking trail and soak up the serenity of this breezy blue and white hideaway. Striped oars, starfish, smooth shells, and ocean scenes blend with shades of teal and aqua for a thoroughly calm space. There are EV chargers behind the post office. It’s around a block and a half.

$65 per night

PLUS