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Vacation rentals in Chebeague Island

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Top-rated vacation rentals in Chebeague Island

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

Guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Cozy warm heater for spring. This yurt is “glampy” inside with leather chairs, pine log bed. The Island Yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Wicked good water. Bring food to prepare. Fire pit. Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to yurt.
Jan. 11 – 18
$202 CAD per night
Guest favourite
Treehouse in Georgetown
Modern Tree Dwelling w/Water Views+Cedar Hot Tub
Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our reviews!).
Nov. 25 – Dec. 2
$594 CAD per night
Guest favourite
Guest suite in Freeport
Solar Suite surrounded by Nature
Solar suite on conservation property offers peaceful getaway. Large sitting room furnished with contemporary sofa, reading area, bedroom nook with natural latex Queen mattress on Japanese platform, kitchen island/toaster oven, mini fridge, dishes, silverware, linen napkins (please note this is not a full kitchen for preparing meals) private bath/shower. On the lower level of our home with private entrance. Cedar hot tub available.
Mar. 23 – 30
$188 CAD per night

Popular amenities for Chebeague Island vacation rentals

Stay near Chebeague Island's top sights

Chebeague Island Inn12 locals recommend
Doughty's Island Market4 locals recommend
Slow Bell Cafe5 locals recommend
Great Chebeague Golf Club3 locals recommend
The Niblic & Gallery3 locals recommend
Museum of Chebeague History, South Road, Chebeague Island, ME3 locals recommend

Other great vacation rentals in Chebeague Island

Guest favourite
Apartment in Harpswell
Sunny Apartment on the Ocean.
Nov. 26 – Dec. 3
$168 CAD per night
Guest favourite
Home in Yarmouth
Beautiful Coastal Maine Getaway
Nov. 11 – 18
$582 CAD per night
Guest favourite
Tiny homes in Freeport
Cozy Rock Cabin #thewaylifeshouldbe
Guest favourite
Guesthouse in Harpswell
Harpswell Studio on Waterview Property! Lobster!
Mar. 13 – 20
$161 CAD per night
Guest favourite
Cottage in Harpswell
Classic Maine Cottage - dock, sauna & kayaks
Sep. 15 – 22
$760 CAD per night
Guest favourite
Guesthouse in Cape Elizabeth
Newly built private guest suite off Shore Road
May 6 – 13
$231 CAD per night
Guest favourite
Home in Lisbon
Unplug at a Beachy Bolthole with Classic New England Style
Feb. 15 – 22
$107 CAD per night
Guest favourite
Guesthouse in Boothbay Harbor
The Sparrow’s Nest Charming Country Cottage
Sep. 29 – Oct. 6
$673 CAD per night
Guest favourite
Guesthouse in Yarmouth
Private Guesthouse in the Woods
Apr. 2 – 9
$239 CAD per night
Home in Yarmouth
Cousins Island Summer Getaway
Jun. 30 – Jul. 7
$455 CAD per night
Guest favourite
Guesthouse in Freeport
Mast Landing Cottage
Apr. 6 – 13
$197 CAD per night
Guest favourite
Apartment in Falmouth
Sweet 2-story 1910 Bungalow near Portland, Beaches
Nov. 23 – 30
$177 CAD per night

Destinations to explore