Book Holiday Homes in Orrs Island

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Featured Holiday Homes in Orrs Island

Sunny Modern Oasis in Portland’s Trendy East End

Sunny Modern Oasis in Portland’s Trendy East End

Portland ME
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Opens in a new windowSunny Modern Oasis in Portland’s Trendy East End
Fantastic Waterfront Views

Fantastic Waterfront Views

Phippsburg ME
The price is AU$566 per night from 15 Jan to 16 Jan
AU$566
15 Jan - 16 Jan 2026
includes taxes & fees
With a stay at this vacation home in Phippsburg (West Point), you'll be within a 15-minute drive of Casco Bay and Popham Beach State Park.
Opens in a new windowFantastic Waterfront Views
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.
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Captain's Guest Room w/private bath. Walk to everything.

Captain's Guest Room w/private bath. Walk to everything.

Bath ME
With a stay at this vacation home in Bath, you'll be within a 10-minute walk of Chocolate Church and Markings Gallery.
Opens in a new windowCaptain's Guest Room w/private bath. Walk to everything.
Large, light filled 4 bedroom house - walk to ocean and ferry

Large, light filled 4 bedroom house - walk to ocean and ferry

Peaks Island ME
With a stay at this vacation home in Peaks Island, you'll be by the ocean, just a 1-minute walk from Casco Bay and 6 minutes by foot from Richard Boyd Art ...
Opens in a new windowLarge, light filled 4 bedroom house - walk to ocean and ferry
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
Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock

Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock

Woolwich ME
Located in Woolwich, this vacation home is within a 5-minute drive of Kennebec River and Markings Gallery.
Opens in a new windowWindward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock
Beautiful house on the Harpswell Peninsula over looking Casco Bay

Beautiful house on the Harpswell Peninsula over looking Casco Bay

Harpswell ME
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.
Opens in a new windowBeautiful house on the Harpswell Peninsula over looking Casco Bay
Lone Pine Cottage Maine - Chef’s Kitchen

Lone Pine Cottage Maine - Chef’s Kitchen

Bath ME
When you stay at this vacation home in Bath, you'll be by the sea, within a 15-minute walk of Maine Maritime Museum and Kennebec River.
Opens in a new windowLone Pine Cottage Maine - Chef’s Kitchen
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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.

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

Holiday houses in Orrs 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 Orrs 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 Orrs Island adventures, obvs.

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

Orrs Island Holiday Homes essential information

Accommodation
551 Holiday Homes
Lowest Price
AU$140
Highest Price
AU$566
Popular accommodation
Sunny Modern Oasis in Portland’s Trendy East End, Fantastic Waterfront Views, Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH., Captain's Guest Room w/private bath. Walk to everything., Large, light filled 4 bedroom house - walk to ocean and ferry, Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views, Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock, Beautiful house on the Harpswell Peninsula over looking Casco Bay, Lone Pine Cottage Maine - Chef’s Kitchen

Top trending hotels in Orrs Island

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$241 per night from 18 Dec to 19 Dec
AU$241
18 Dec - 19 Dec
includes taxes & fees
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Opens in a new windowPortland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
With a stay at Portland Regency Hotel & Spa, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Opens in a new windowPortland Regency Hotel & Spa
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 22 Dec to 23 Dec
AU$203
22 Dec - 23 Dec
includes taxes & fees
With a stay at Canopy by Hilton Portland Waterfront in Portland (Downtown Portland), you'll be within a 10-minute drive of Maine Mall and Casco Bay.
Opens in a new windowCanopy by Hilton Portland Waterfront
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Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$140 per night from 18 Dec to 19 Dec
AU$140
18 Dec - 19 Dec
includes taxes & fees
With a stay at Clarion Hotel Portland Airport ME in Portland, you'll be near the airport, within a 15-minute walk of Thompson's Point and Portland Exposition ...
Opens in a new windowClarion Hotel Portland Airport ME
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See all available properties in Orrs 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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.