Book Holiday Homes in Squirrel Island

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Featured Holiday Homes in Squirrel Island

Peace in Pemaquid - Ocean Sunsets & Stargazing

Peace in Pemaquid - Ocean Sunsets & Stargazing

Bristol
When you stay at this vacation home in Pemaquid, you'll be by the sea, within a 5-minute drive of Pemaquid Craft Co-op and Colonial Pemaquid State Historic ...
Peace in Pemaquid - Ocean Sunsets & Stargazing
Bayfront home with 270-degree views, large deck & porch - near Popham Beach

Bayfront home with 270-degree views, large deck & porch - near Popham Beach

Phippsburg
With a stay at this vacation home in Phippsburg, you'll be on the beach, just steps from Casco Bay and a 3-minute drive from Kennebec River.
Bayfront home with 270-degree views, large deck & porch - near Popham Beach
Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away

Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away

Permaquid Point
With a stay at this vacation home in New Harbor (Pemaquid Point), you'll be within a 5-minute drive of Pemaquid Point Lighthouse Park and Pemaquid Craft ...
Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away
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Lofty cottage

Lofty cottage

Harpswell
The price is AU$566 per night from 26 Nov to 27 Nov
AU$566
includes taxes & fees
26 Nov - 27 Nov
Located in Harpswell, this vacation home is by the ocean, a 1-minute drive from Casco Bay and 9 minutes from Paddleworks.
Lofty cottage
More then a Motel With Garden , Renovated Rooms at heart of Boothbay

More then a Motel With Garden , Renovated Rooms at heart of Boothbay

2 out of 5
Boothbay
With a stay at this vacation home in Boothbay, you'll be a 3-minute walk from Boothbay Railway Village and 7 minutes by foot from Dolphin Mini Golf.
More then a Motel With Garden , Renovated Rooms at heart of Boothbay
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining &  Marina

Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina

Boothbay Harbor
With a stay at this vacation home, you'll be centrally located in Boothbay Harbor, just a 5-minute walk from Boothbay Harbor Memorial Library and 6 minutes by ...
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome

Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome

Boothbay
A stay at this vacation home places you in the heart of Boothbay, within a 5-minute drive of Coastal Maine Botanical Gardens and Hodgdon Island.
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun

Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun

Boothbay Harbor
When you a stay at this vacation home in Boothbay Harbor, you'll be by the sea, just steps from Cabbage Island and Linekin Bay.
Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun
Spectacular Ocean Views from Every Room

Spectacular Ocean Views from Every Room

South Bristol
With a stay at this vacation home in South Bristol (Christmas Cove), you'll be 9 minutes by car from Fort Point.
Spectacular Ocean Views from Every Room
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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.

Squirrel 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 Squirrel Island vacation homes are the perfect way for you to wing it.

Holiday houses in Squirrel 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 Squirrel 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 Squirrel Island adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Squirrel 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 Squirrel 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.

Squirrel Island Holiday Homes essential information

Accommodation
362 Holiday Homes
Lowest Price
AU$184
Highest Price
AU$566
Popular accommodation
Peace in Pemaquid - Ocean Sunsets & Stargazing , Bayfront home with 270-degree views, large deck & porch - near Popham Beach, Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away, Lofty cottage , More then a Motel With Garden , Renovated Rooms at heart of Boothbay, Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina, Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome, Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun, Spectacular Ocean Views from Every Room

Top trending hotels in Squirrel Island

The Brunswick Hotel

The Brunswick Hotel

3 out of 5
4 Noble St, Brunswick, ME
Fully refundableReserve now, pay when you stay
The price is AU$214 per night from 26 Nov to 27 Nov
AU$214
includes taxes & fees
26 Nov - 27 Nov
A stay at The Brunswick Hotel places you in the heart of Brunswick, steps from Casco Bay and Maine Street.
The Brunswick Hotel
Tugboat Inn

Tugboat Inn

3 out of 5
80 Commercial St., Boothbay Harbor, ME
The price is AU$235 per night from 26 Nov to 27 Nov
AU$235
includes taxes & fees
26 Nov - 27 Nov
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
The Federal

The Federal

2.5 out of 5
10 Water St, Brunswick, ME
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 1 Dec to 2 Dec
AU$186
includes taxes & fees
1 Dec - 2 Dec
With a stay at The Federal in Brunswick, you'll be just steps from Casco Bay and Androscoggin River.
The Federal
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Residence Inn Bath Brunswick Area

Residence Inn Bath Brunswick Area

3 out of 5
139 Richardson St., Bath, ME
Fully refundableReserve now, pay when you stay
The price is AU$184 per night from 15 Dec to 16 Dec
AU$184
includes taxes & fees
15 Dec - 16 Dec
Located in Bath, Residence Inn Bath Brunswick Area is within a 5-minute drive of Casco Bay and Bath Visitor Information Center.
Residence Inn Bath Brunswick Area
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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.