Book Holiday Homes in Squirrel Island

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Featured Holiday Homes in Squirrel Island

2 bedroom  1 bath, large deck and dock, on the water in peaceful cove,   Year

2 bedroom 1 bath, large deck and dock, on the water in peaceful cove, Year

Boothbay
When you stay at this vacation home in East Boothbay, you'll be near the beach, within a 5-minute drive of Linekin Bay and Grimes Cove Beach.
2 bedroom 1 bath, large deck and dock, on the water in peaceful cove, Year
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

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

Boothbay Harbor
With a stay at this vacation home in Boothbay Harbor, you'll be a 4-minute walk from Boothbay Harbor Memorial Library and 5 minutes by foot from Boothbay Harbor ...
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
Captain's Quarters 2BR Apartment. Walk to Everything!

Captain's Quarters 2BR Apartment. Walk to Everything!

Bath
The price is AU$404 per night from 23 Sept to 24 Sept
AU$404
23 Sept - 24 Sept
includes taxes & fees
With a stay at this vacation home in Bath, you'll be within a 10-minute walk of Chocolate Church and Markings Gallery.
Captain's Quarters 2BR Apartment. Walk to Everything!
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Beautiful house on the Harpswell Peninsula over looking Casco Bay

Beautiful house on the Harpswell Peninsula over looking Casco Bay

Harpswell
With a stay at this vacation home in Harpswell, you'll be by the ocean, just steps from Casco Bay and a 4-minute drive from Mitchell Field.
Beautiful house on the Harpswell Peninsula over looking Casco Bay
Beautiful Oceanfront House- Stunning Water Views

Beautiful Oceanfront House- Stunning Water Views

Harpswell
Located in Harpswell, this vacation home is a 1-minute drive from Casco Bay and 7 minutes from Androscoggin River.
Beautiful Oceanfront House- Stunning Water Views
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Bailey Island
With a stay at this vacation home in Bailey Island, you'll be on the beach, just a 1-minute walk from Casco Bay and 14 minutes by foot from Mackerel Cove.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Camp Forever cottage

Camp Forever cottage

Harpswell
The price is AU$434 per night from 1 Oct to 2 Oct
AU$434
1 Oct - 2 Oct
includes taxes & fees
Located in Harpswell, this vacation home is by the ocean, a 1-minute drive from Casco Bay and 9 minutes from Paddleworks.
Camp Forever cottage
Make Shimmering River Retreat your Maine Coastal getaway!

Make Shimmering River Retreat your Maine Coastal getaway!

Westport Island
Located in Wiscasset, this vacation home is by the ocean, within a 15-minute drive of Monkey C Monkey Do and Long Ledge.
Make Shimmering River Retreat your Maine Coastal getaway!
Charming 2-bedroom house in small-town neighborhood

Charming 2-bedroom house in small-town neighborhood

Bath
With a stay at this vacation home in Bath, you'll be within a 15-minute walk of Chocolate Church and Waterfront Park.
Charming 2-bedroom house in small-town neighborhood
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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
549 Holiday Homes
Lowest Price
AU$220
Highest Price
AU$434
Popular accommodation
2 bedroom 1 bath, large deck and dock, on the water in peaceful cove, Year , Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor, Captain's Quarters 2BR Apartment. Walk to Everything!, Beautiful house on the Harpswell Peninsula over looking Casco Bay, Beautiful Oceanfront House- Stunning Water Views, New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach, Camp Forever cottage, Make Shimmering River Retreat your Maine Coastal getaway!, Charming 2-bedroom house in small-town neighborhood

Top trending hotels in Squirrel Island

Ocean Gate Resort

Ocean Gate Resort

3 out of 5
70 Ocean Gate Rd, Southport, ME
The price is AU$267 per night from 7 Sept to 8 Sept
AU$267
7 Sept - 8 Sept
includes taxes & fees
Located in Southport, Ocean Gate Resort is by the ocean, a 4-minute drive from Hendricks Hill Museum and 5 minutes from Juniper Point.
Ocean Gate Resort
Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue, Boothbay Harbor, ME
The price is AU$285 per night from 15 Sept to 16 Sept
AU$285
15 Sept - 16 Sept
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 ...
Flagship Inn and Suites
Best Western Plus Brunswick Bath

Best Western Plus Brunswick Bath

2.5 out of 5
71 Gurnet Road, Brunswick, ME
Fully refundableReserve now, pay when you stay
The price is AU$220 per night from 5 Oct to 6 Oct
AU$220
5 Oct - 6 Oct
includes taxes & fees
With a stay at Best Western Plus Brunswick Bath in Brunswick, you'll be in a shopping district, just steps from Casco Bay and a 2-minute drive from Brunswick ...
Best Western Plus Brunswick Bath
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Boothbay Harbor Inn

Boothbay Harbor Inn

2.5 out of 5
31 Atlantic Ave, Boothbay Harbor, ME
The price is AU$318 per night from 7 Sept to 8 Sept
AU$318
7 Sept - 8 Sept
includes taxes & fees
With a stay at Boothbay Harbor Inn in Boothbay Harbor, you'll be on the waterfront, just a 5-minute walk from Fisherman's Memorial Park and 9 minutes by foot ...
Boothbay Harbor Inn
Don't see what you're looking for?
See all available properties in Squirrel 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.