Book Holiday Homes in Monhegan Island

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Featured Holiday Homes in Monhegan Island

Beautifully renovated home w/ prime location - walk to the footbridge & downtown

Beautifully renovated home w/ prime location - walk to the footbridge & downtown

Boothbay Harbor
With a stay at this vacation home, you'll be centrally located in Boothbay Harbor, just a 4-minute walk from Fisherman's Memorial Park and 8 minutes by foot ...
Beautifully renovated home w/ prime location - walk to the footbridge & downtown
Tranquil And Peaceful Vacation Getaway Just Waiting To Welcome You

Tranquil And Peaceful Vacation Getaway Just Waiting To Welcome You

Bristol
With a stay at this vacation home, you'll be centrally located in Bristol, within a 15-minute drive of Pemaquid Craft Co-op and Biscay Pond.
Tranquil And Peaceful Vacation Getaway Just Waiting To Welcome You
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
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 ...
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
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Home In Boothbay - Holiday Getaway

Home In Boothbay - Holiday Getaway

Boothbay
Located in Boothbay, this vacation home is in a rural location, within a 15-minute walk of The Boothbay Playhouse and Dolphin Mini Golf.
Home In Boothbay - Holiday Getaway
Welcome to Owl House - Your Coastal Retreat in East Boothbay!

Welcome to Owl House - Your Coastal Retreat in East Boothbay!

Boothbay
With a stay at this vacation home in East Boothbay (Ocean Point), you'll be a 4-minute walk from Linekin Bay and 11 minutes by foot from Grimes Cove Beach.
Welcome to Owl House - Your Coastal Retreat in East Boothbay!
Ambleside- a beautifully renovated home in Boothbay Harbor Maine!

Ambleside- a beautifully renovated home in Boothbay Harbor Maine!

Boothbay Harbor
When you stay at this vacation home in Boothbay Harbor, you'll be by the sea, within a 15-minute walk of Fisherman's Memorial Park and Linekin Bay.
Ambleside- a beautifully renovated home in Boothbay Harbor Maine!
Historical New England home with outdoor shower - near downtown

Historical New England home with outdoor shower - near downtown

Boothbay Harbor
Located in Boothbay Harbor, this vacation home is by the sea, within a 5-minute drive of Burnt Island Living Lighthouse and Boothbay Harbor Marina.
Historical New England home with outdoor shower - near downtown
Coastal bungalow with large yard, beautiful kitchen, & great location

Coastal bungalow with large yard, beautiful kitchen, & great location

Boothbay Harbor
When you stay at this vacation home in Boothbay Harbor, you'll be by the sea, within a 15-minute walk of Fisherman's Memorial Park and Linekin Bay.
Coastal bungalow with large yard, beautiful kitchen, & great location
Harborview Perch... spacious & open floorplan, privacy, harbor view, amenities

Harborview Perch... spacious & open floorplan, privacy, harbor view, amenities

Boothbay Harbor
A stay at this vacation home places you in the heart of Boothbay Harbor, within a 5-minute drive of Burnt Island Living Lighthouse and Boothbay Harbor ...
Harborview Perch... spacious & open floorplan, privacy, harbor view, amenities
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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
288 Holiday Homes
Lowest Price
AU$217
Highest Price
AU$710
Popular accommodation
Beautifully renovated home w/ prime location - walk to the footbridge & downtown, Tranquil And Peaceful Vacation Getaway Just Waiting To Welcome You, Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views, Home In Boothbay - Holiday Getaway, Welcome to Owl House - Your Coastal Retreat in East Boothbay! , Ambleside- a beautifully renovated home in Boothbay Harbor Maine!, Historical New England home with outdoor shower - near downtown, Coastal bungalow with large yard, beautiful kitchen, & great location, Harborview Perch... spacious & open floorplan, privacy, harbor view, amenities

Top trending hotels in Monhegan Island

Tugboat Inn

Tugboat Inn

3 out of 5
80 Commercial St., Boothbay Harbor, ME
The price is AU$248 per night from 1 May to 2 May
AU$248
includes taxes & fees
1 May - 2 May
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.
Tugboat Inn
Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue, Boothbay Harbor, ME
The price is AU$217 per night from 28 Apr to 29 Apr
AU$217
includes taxes & fees
28 Apr - 29 Apr
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 ...
Flagship Inn and Suites
Spruce Point Inn

Spruce Point Inn

3.5 out of 5
88 Grandview Ave, Boothbay Harbor, ME
The price is AU$710 per night from 18 May to 19 May
AU$710
includes taxes & fees
18 May - 19 May
Located in Boothbay Harbor, Spruce Point Inn is on the waterfront, a 4-minute walk from Linekin Bay and within a 5-minute drive of Fisherman's Memorial ...
Spruce Point Inn
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Smuggler's Cove Inn

Smuggler's Cove Inn

2.5 out of 5
727 Ocean Point Road, East Boothbay, ME
The price is AU$321 per night from 8 May to 9 May
AU$321
includes taxes & fees
8 May - 9 May
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.
Smuggler's Cove Inn
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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.