Book Holiday Homes in Monhegan Island

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Featured Holiday Homes in Monhegan Island

Downtown Waterfront Cottage with shoreline sitting room

Downtown Waterfront Cottage with shoreline sitting room

Boothbay Harbor ME
With a stay at this vacation home, you'll be centrally located in Boothbay Harbor, just a 4-minute walk from Boothbay Harbor Memorial Library and 5 minutes by ...
Opens in a new windowDowntown Waterfront Cottage with shoreline sitting room
Downtown Boothbay Harbor, 2-Story Cottage

Downtown Boothbay Harbor, 2-Story Cottage

Boothbay Harbor ME
With a stay at this vacation home in Boothbay Harbor, you'll be within a 5-minute walk of Opera House at Boothbay Harbor and Boothbay Region Historical Society ...
Opens in a new windowDowntown Boothbay Harbor, 2-Story Cottage
Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE

Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE

East Boothbay ME
A stay at this vacation home places you in the heart of East Boothbay, within a 5-minute drive of Linekin Bay and Grimes Cove Beach.
Opens in a new windowSmuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE
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Peaceful Lake waterfront! Full Kitchen! Heat&AC! 5min to town, 8min to Garden!

Peaceful Lake waterfront! Full Kitchen! Heat&AC! 5min to town, 8min to Garden!

Boothbay Harbor ME
Located in Boothbay Harbor, this vacation home is on a lake, within a 5-minute drive of Boothbay Harbor Marina and Burnt Island Living Lighthouse.
Opens in a new windowPeaceful Lake waterfront! Full Kitchen! Heat&AC! 5min to town, 8min to Garden!
Boothbay Harbor Woodland Retreat

Boothbay Harbor Woodland Retreat

Boothbay Harbor ME
With a stay at this vacation home in Boothbay Harbor, you'll be within a 5-minute drive of Boothbay Harbor Marina and Burnt Island Living Lighthouse.
Opens in a new windowBoothbay Harbor Woodland Retreat
Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.

Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.

Boothbay Harbor ME
When you stay at this vacation home in Boothbay Harbor, you'll be on the waterfront, just steps from Linekin Bay and Barrett Park.
Opens in a new windowEnjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.
Home In Boothbay - Holiday Getaway

Home In Boothbay - Holiday Getaway

Boothbay ME
Located in Boothbay, this vacation home is in a rural location, within a 15-minute walk of The Boothbay Playhouse and Dolphin Mini Golf.
Opens in a new windowHome In Boothbay - Holiday Getaway
Jordan Cottage by Sea Maine

Jordan Cottage by Sea Maine

Boothbay Harbor ME
With a stay at this vacation home in Boothbay Harbor, you'll be steps from Linekin Bay and a 4-minute drive from Carousel Music Theater.
Opens in a new windowJordan Cottage by Sea Maine
Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Boothbay Harbor ME
A stay at this vacation home places you in the heart of Boothbay Harbor, steps from Boothbay Region Land Trust and Boothbay Region Historical Society ...
Opens in a new windowNewly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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
301 Holiday Homes
Lowest Price
AU$256
Highest Price
AU$287
Popular accommodation
Downtown Waterfront Cottage with shoreline sitting room, Downtown Boothbay Harbor, 2-Story Cottage, Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE, Peaceful Lake waterfront! Full Kitchen! Heat&AC! 5min to town, 8min to Garden!, Boothbay Harbor Woodland Retreat, Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly., Home In Boothbay - Holiday Getaway, Jordan Cottage by Sea Maine, Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Top trending hotels in Monhegan Island

Sunsets Galore 
Peace & Quiet
Beautiful 3-bedroom home on Monhegan Island.

Sunsets Galore Peace & Quiet Beautiful 3-bedroom home on Monhegan Island.

Monhegan Island ME
With a stay at this vacation home in Monhegan Island, you'll be within a 10-minute walk of Fish Beach and Lupine Gallery.
Opens in a new windowSunsets Galore Peace & Quiet Beautiful 3-bedroom home on Monhegan Island.
Tugboat Inn

Tugboat Inn

3 out of 5
80 Commercial St. Boothbay Harbor ME
The price is AU$256 per night from 14 May to 15 May
AU$256
14 May - 15 May
includes taxes & fees
With a stay at Tugboat Inn in Boothbay Harbor, you'll be within a 5-minute walk of Burnt Island Living Lighthouse and Boothbay Harbor Marina.
Opens in a new windowTugboat Inn
Smuggler's Cove Inn

Smuggler's Cove Inn

2.5 out of 5
727 Ocean Point Road East Boothbay ME
The price is AU$287 per night from 14 May to 15 May
AU$287
14 May - 15 May
includes taxes & fees
Located in East Boothbay, Smuggler's Cove Inn is by the ocean, within a 10-minute drive of Boothbay Harbor Memorial Library and Boothbay Harbor Marina.
Opens in a new windowSmuggler's Cove Inn
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Bluebird Ocean Point Inn

Bluebird Ocean Point Inn

3 out of 5
191 Shore Road East Boothbay ME
The price is AU$262 per night from 29 May to 30 May
AU$262
29 May - 30 May
includes taxes & fees
With a stay at Bluebird Ocean Point Inn in East Boothbay (Ocean Point), you'll be steps from Linekin Bay and a 3-minute drive from Grimes Cove Beach.
Opens in a new windowBluebird Ocean Point Inn
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Picks

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