Book Holiday Homes in Monhegan Island

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Featured Holiday Homes in Monhegan Island

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, within a 5-minute walk of Boothbay Region Land Trust and Boothbay Region Historical ...
Opens in a new windowNewly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

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

Boothbay Harbor ME
With a stay at this vacation home in Boothbay Harbor, you'll be on the beach, just a 4-minute walk from Boothbay Harbor Memorial Library and 6 minutes by foot ...
Opens in a new windowDowntown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
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 a 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.
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Oceanfront Retreat with Dock, Boothbay Harbor

Oceanfront Retreat with Dock, Boothbay Harbor

2 out of 5
Boothbay Harbor ME
A stay at this vacation home places you in the heart of Boothbay Harbor, within a 15-minute walk of Fisherman's Memorial Park and Linekin Bay.
Opens in a new windowOceanfront Retreat with Dock, Boothbay Harbor
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor with private dock

The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor with private dock

Boothbay Harbor ME
With a stay at this vacation home in Boothbay Harbor, you'll be on the waterfront, just a 3-minute walk from Opera House at Boothbay Harbor and 5 minutes by ...
Opens in a new windowThe Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor with private dock
Downtown Boothbay 3BR – Harbor Views, Private Deck, Walk Everywhere

Downtown Boothbay 3BR – Harbor Views, Private Deck, Walk Everywhere

Boothbay Harbor ME
A stay at this vacation home places you in the heart of Boothbay Harbor, within a 5-minute walk of Burnt Island Living Lighthouse and Boothbay Harbor Memorial ...
Opens in a new windowDowntown Boothbay 3BR – Harbor Views, Private Deck, Walk Everywhere
Dog-friendly, waterfront home on St. George River with shore access, great views

Dog-friendly, waterfront home on St. George River with shore access, great views

St. George ME
When you stay at this vacation home in Port Clyde, you'll be on the beach and 12 minutes by car from Marshall Point Lighthouse.
Opens in a new windowDog-friendly, waterfront home on St. George River with shore access, great views
Historic "Wilbur Morse" Friendship Maine Ocean Home

Historic "Wilbur Morse" Friendship Maine Ocean Home

Friendship ME
With a stay at this vacation home in Friendship, you'll be on the waterfront, and 10.7 mi (17.3 km) from St. George River and 12.2 mi (19.6 km) from Maine State ...
Opens in a new windowHistoric "Wilbur Morse" Friendship Maine Ocean Home
Dazzling ocean-view house with fireplace, deck, firepit, central AC, & W/D

Dazzling ocean-view house with fireplace, deck, firepit, central AC, & W/D

Tenants Harbor ME
Located in Tenants Harbor, this vacation home is by the ocean, within a 15-minute drive of Tenants Harbor Marina and Marshall Point Lighthouse.
Opens in a new windowDazzling ocean-view house with fireplace, deck, firepit, central AC, & W/D
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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
249 Holiday Homes
Lowest Price
AU$200
Highest Price
AU$359
Popular accommodation
Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH., Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views, Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly., Oceanfront Retreat with Dock, Boothbay Harbor, The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor with private dock, Downtown Boothbay 3BR – Harbor Views, Private Deck, Walk Everywhere, Dog-friendly, waterfront home on St. George River with shore access, great views, Historic "Wilbur Morse" Friendship Maine Ocean Home , Dazzling ocean-view house with fireplace, deck, firepit, central AC, & W/D

Top trending hotels in Monhegan Island

Tugboat Inn

Tugboat Inn

3 out of 5
80 Commercial St. Boothbay Harbor ME
The price is AU$260 per night from 25 Dec to 26 Dec
AU$260
25 Dec - 26 Dec
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
Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue Boothbay Harbor ME
The price is AU$200 per night from 12 Jan to 13 Jan
AU$200
12 Jan - 13 Jan 2026
includes taxes & fees
With a stay at Flagship Inn and Suites in Boothbay Harbor, you'll be a 1-minute walk from Carousel Music Theater and 6 minutes by foot from Boothbay Region Land ...
Opens in a new windowFlagship Inn and Suites
Bluebird Ocean Point Inn

Bluebird Ocean Point Inn

3 out of 5
191 Shore Road East Boothbay ME
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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Harborage Inn on the Oceanfront

Harborage Inn on the Oceanfront

3.5 out of 5
75 Townsend Avenue Boothbay Harbor ME
The price is AU$359 per night from 1 Jan to 2 Jan
AU$359
1 Jan - 2 Jan 2026
includes taxes & fees
With a stay at Harborage Inn on the Oceanfront, you'll be centrally located in Boothbay Harbor, steps from Opera House at Boothbay Harbor and within a 5-minute ...
Opens in a new windowHarborage Inn on the Oceanfront
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See all available properties in Monhegan Island
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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.

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^Subject to availability and chosen travel dates.