Book Holiday Homes in Orrs Island

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Orrs Island

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Portland
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.
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Lakefront House

Lakefront House

Windham
The price is AU$1,251 per night from 20 Jan to 21 Jan
AU$1,251
includes taxes & fees
20 Jan - 21 Jan 2025
Located in Windham, this vacation home is on the waterfront, within a 10-minute drive of Maine Wildlife Park and Mercy Primary Care.
Lakefront House
Amazing riverfront home with private deck, views, private dock, & fireplace

Amazing riverfront home with private deck, views, private dock, & fireplace

West Bath
Located in Bath, this vacation home is by the ocean, within a 15-minute drive of Casco Bay and Maine Maritime Museum.
Amazing riverfront home with private deck, views, private dock, & fireplace
Save an average of 15% on thousands of hotels when you're signed in
Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Portland
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.
Beautiful Combo Home Located in Downtown Portland - Close to the Beach
Lofty cottage

Lofty cottage

Harpswell
Located in Harpswell, this vacation home is by the ocean, a 1-minute drive from Casco Bay and 9 minutes from Paddleworks.
Lofty cottage
Oceanfront Cabin-Castle in Maine Woods

Oceanfront Cabin-Castle in Maine Woods

Georgetown
Located in Georgetown, this vacation home is by the ocean, a 1-minute drive from Reid State Park and 8 minutes from Georgetown Historical Society.
Oceanfront Cabin-Castle in Maine Woods
Charming 110-year former Inn 10' from the Ocean!

Charming 110-year former Inn 10' from the Ocean!

South Portland
With a stay at this vacation home in South Portland (Willard), you'll be within a 15-minute drive of Maine Mall and Casco Bay.
Charming 110-year former Inn 10' from the Ocean!
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
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.

Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.

Boothbay Harbor
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 ...
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.
Don't see what you're looking for?
See all available properties in Orrs Island
View all properties
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
430 Holiday Homes
Lowest Price
AU$166
Highest Price
AU$1,251
Popular accommodation
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub, Lakefront House, Amazing riverfront home with private deck, views, private dock, & fireplace, Beautiful Combo Home Located in Downtown Portland - Close to the Beach, Lofty cottage , Oceanfront Cabin-Castle in Maine Woods, Charming 110-year former Inn 10' from the Ocean!, Bayfront home with 270-degree views, large deck & porch - near Popham Beach, Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.

Top trending hotels in Orrs Island

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$176 per night from 7 Jan to 8 Jan
AU$176
includes taxes & fees
7 Jan - 8 Jan 2025
With a stay at The Westin Portland Harborview, you'll be centrally located in Portland, steps from State Theatre and Portland Museum of Art.
The Westin Portland Harborview
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$166 per night from 25 Dec to 26 Dec
AU$166
includes taxes & fees
25 Dec - 26 Dec
With a stay at Ramada Plaza by Wyndham Portland in Portland (Nasons Corner), you'll be within a 10-minute drive of Maine Mall and Happy Wheels Skate Center.
Ramada Plaza by Wyndham Portland
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$258 per night from 25 Dec to 26 Dec
AU$258
includes taxes & fees
25 Dec - 26 Dec
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.
Portland Harbor Hotel
Save an average of 15% on thousands of hotels when you're signed in
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$254 per night from 5 Jan to 6 Jan
AU$254
includes taxes & fees
5 Jan - 6 Jan 2025
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.
Canopy by Hilton Portland Waterfront
Don't see what you're looking for?
See all available properties in Orrs Island
View all properties
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.