Book Holiday Homes in Monhegan Island
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Featured Holiday Homes in Monhegan Island

Slow Down & Go Back in Time-Relax Completely in Our Maine Home

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Downtown Boothbay Harbor, 2-Story Cottage

Room 15 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle

Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

Well-located, dog-friendly home - walk to footbridge & Barrett Park

Oceanfront home on Lobster Cove with deck & shared firepit - walk to town

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

More then a Motel With Garden , Renovated Rooms at heart of Boothbay
Monhegan Island Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Monhegan Island vacation homes are the perfect way for you to wing it.
Holiday houses in Monhegan Island let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Monhegan Island in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Monhegan Island adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Monhegan Island with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Monhegan Island vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Monhegan Island Holiday Homes essential information
Accommodation | 288 Holiday Homes |
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Highest Price | |
Popular accommodation | Slow Down & Go Back in Time-Relax Completely in Our Maine Home, Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views, Downtown Boothbay Harbor, 2-Story Cottage, Room 15 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle, Century-old oceanfront home with wraparound porch - walk downtown, dogs OK, Well-located, dog-friendly home - walk to footbridge & Barrett Park, Oceanfront home on Lobster Cove with deck & shared firepit - walk to town, Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor, More then a Motel With Garden , Renovated Rooms at heart of Boothbay |
More accommodations in Monhegan Island
Top trending hotels in Monhegan Island

Tugboat Inn

Flagship Inn and Suites

Fishermans Wharf Inn

Ocean Gate Resort
More ways to explore Monhegan Island
Top picks
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^Subject to availability and chosen travel dates.