Book Holiday Homes in Orrs Island

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Featured Holiday Homes in Orrs Island

Beautiful Oceanfront House- Stunning Water Views

Beautiful Oceanfront House- Stunning Water Views

Harpswell ME
Located in Harpswell, this vacation home is a 1-minute drive from Casco Bay and 7 minutes from Androscoggin River.
Opens in a new windowBeautiful Oceanfront House- Stunning Water Views
Boothbay Harbor Woodland Retreat

Boothbay Harbor Woodland Retreat

Boothbay Harbor ME
With a stay at this vacation home in Boothbay Harbor, you'll be within a 5-minute drive of Boothbay Harbor Marina and Burnt Island Living Lighthouse.
Opens in a new windowBoothbay Harbor Woodland Retreat
Centerview cottage

Centerview cottage

Harpswell ME
The price is AU$658 per night from 15 May to 16 May
AU$658
15 May - 16 May
includes taxes & fees
Located in Harpswell, this vacation home is by the ocean, within a 15-minute drive of Paddleworks and Bailey Island Bridge.
Opens in a new windowCenterview cottage
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Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE

Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE

East Boothbay ME
A stay at this vacation home places you in the heart of East Boothbay, within a 5-minute drive of Linekin Bay and Grimes Cove Beach.
Opens in a new windowSmuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE
5 Star Back Cove Apartment with water view!

5 Star Back Cove Apartment with water view!

Portland ME
With a stay at this vacation home in Portland (Back Cove), you'll be a 4-minute drive from Thompson's Point and 9 minutes from Maine Mall.
Opens in a new window5 Star Back Cove Apartment with water view!
Downtown Waterfront Cottage with shoreline sitting room

Downtown Waterfront Cottage with shoreline sitting room

Boothbay Harbor ME
With a stay at this vacation home, you'll be centrally located in Boothbay Harbor, just a 4-minute walk from Boothbay Harbor Memorial Library and 5 minutes by ...
Opens in a new windowDowntown Waterfront Cottage with shoreline sitting room
Rare West End Home • Walk to Old Port, Harbor View

Rare West End Home • Walk to Old Port, Harbor View

Portland ME
With a stay at this vacation home in Portland (West End), you'll be a 5-minute drive from Thompson's Point and 8 minutes from Maine Mall.
Opens in a new windowRare West End Home • Walk to Old Port, Harbor View
Captain's Guest Room w/private bath. Walk to everything.

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

Bath ME
The price is AU$204 per night from 15 May to 16 May
AU$204
15 May - 16 May
includes taxes & fees
With a stay at this vacation home in Bath, you'll be within a 10-minute walk of Chocolate Church Arts Center and Bath Center for the Arts.
Opens in a new windowCaptain's Guest Room w/private bath. Walk to everything.
Summer 2026 ! Kayak on the Kennebec " EVERYTHING you need "

Summer 2026 ! Kayak on the Kennebec " EVERYTHING you need "

Phippsburg ME
A stay at this vacation home places you in the heart of Phippsburg, a 1-minute drive from Casco Bay and 7 minutes from Maine Maritime Museum.
Opens in a new windowSummer 2026 ! Kayak on the Kennebec " EVERYTHING you need "
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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
525 Holiday Homes
Lowest Price
AU$194
Highest Price
AU$658
Popular accommodation
Beautiful Oceanfront House- Stunning Water Views, Boothbay Harbor Woodland Retreat, Centerview cottage, Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE, 5 Star Back Cove Apartment with water view!, Downtown Waterfront Cottage with shoreline sitting room, Rare West End Home • Walk to Old Port, Harbor View, Captain's Guest Room w/private bath. Walk to everything., Summer 2026 ! Kayak on the Kennebec " EVERYTHING you need "

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$335 per night from 25 May to 26 May
AU$335
25 May - 26 May
includes taxes & fees
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, a 5-minute drive from Thompson's Point and 9 minutes from Maine Mall.
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
The price is AU$250 per night from 27 May to 28 May
AU$250
27 May - 28 May
includes taxes & fees
With a stay at Portland Regency Hotel & Spa, you'll be centrally located in Portland, within a 10-minute drive of Thompson's Point and Maine Mall.
Opens in a new windowPortland Regency Hotel & Spa
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$269 per night from 26 May to 27 May
AU$269
26 May - 27 May
includes taxes & fees
Located in Portland (Downtown Portland), Cambria Hotel Portland Downtown-Old Port is within a 10-minute drive of Thompson's Point and Maine Mall.
Opens in a new windowCambria Hotel Portland Downtown-Old Port
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Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
939 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$194 per night from 17 May to 18 May
AU$194
17 May - 18 May
includes taxes & fees
With a stay at Inn at St John Portland In-Town, you'll be centrally located in Portland, a short 7-minute walk from Maine Medical Center and 14 minutes by foot ...
Opens in a new windowInn at St John Portland In-Town
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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.

Top Picks

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^Subject to availability and chosen travel dates.