Book Holiday Homes in Orrs Island

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Featured Holiday Homes in Orrs Island

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

Cumberland
With a stay at this vacation home, you'll be centrally located in Cumberland Center, within a 15-minute drive of Thompson's Point and LL Bean Flagship ...
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries

Portland
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Thompson's Point and Maine Mall.
The Globe House on Munjoy Hill - Walk to Breweries
Rent a room in the gorgeous Holt House

Rent a room in the gorgeous Holt House

Portland
With a stay at this vacation home in Portland (Parkside), you'll be a 3-minute drive from Thompson's Point and 8 minutes from Maine Mall.
Rent a room in the gorgeous Holt House
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Beautifully renovated home w/ prime location - walk to the footbridge & downtown

Beautifully renovated home w/ prime location - walk to the footbridge & downtown

Boothbay Harbor
With a stay at this vacation home, you'll be centrally located in Boothbay Harbor, just a 4-minute walk from Fisherman's Memorial Park and 8 minutes by foot ...
Beautifully renovated home w/ prime location - walk to the footbridge & downtown
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
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 ...
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Bailey Island
A stay at this vacation home places you in the heart of Bailey Island, steps from Casco Bay and Bailey Island Bridge.
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Home In Boothbay - Holiday Getaway

Home In Boothbay - Holiday Getaway

Boothbay
Located in Boothbay, this vacation home is in a rural location, within a 15-minute walk of The Boothbay Playhouse and Dolphin Mini Golf.
Home In Boothbay - Holiday Getaway
Welcome to Owl House - Your Coastal Retreat in East Boothbay!

Welcome to Owl House - Your Coastal Retreat in East Boothbay!

Boothbay
With a stay at this vacation home in East Boothbay (Ocean Point), you'll be a 4-minute walk from Linekin Bay and 11 minutes by foot from Grimes Cove Beach.
Welcome to Owl House - Your Coastal Retreat in East Boothbay!
Ambleside- a beautifully renovated home in Boothbay Harbor Maine!

Ambleside- a beautifully renovated home in Boothbay Harbor Maine!

Boothbay Harbor
When you stay at this vacation home in Boothbay Harbor, you'll be by the sea, within a 15-minute walk of Fisherman's Memorial Park and Linekin Bay.
Ambleside- a beautifully renovated home in Boothbay Harbor Maine!
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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
570 Holiday Homes
Lowest Price
AU$146
Highest Price
AU$352
Popular accommodation
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!, The Globe House on Munjoy Hill - Walk to Breweries, Rent a room in the gorgeous Holt House, Beautifully renovated home w/ prime location - walk to the footbridge & downtown, Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views, Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary, Home In Boothbay - Holiday Getaway, Welcome to Owl House - Your Coastal Retreat in East Boothbay! , Ambleside- a beautifully renovated home in Boothbay Harbor Maine!

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$237 per night from 26 May to 27 May
AU$237
includes taxes & fees
26 May - 27 May
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
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$352 per night from 4 May to 5 May
AU$352
includes taxes & fees
4 May - 5 May
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.
Portland Harbor Hotel
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$146 per night from 30 Apr to 1 May
AU$146
includes taxes & fees
30 Apr - 1 May
With a stay at Clarion Hotel Portland in Portland, you'll be near the airport, within a 15-minute walk of Thompson's Point and Portland Exposition Building.
Clarion Hotel Portland
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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$300 per night from 30 Apr to 1 May
AU$300
includes taxes & fees
30 Apr - 1 May
Located in Portland (East Bayside), Cambria Hotel Portland Downtown-Old Port is within a 10-minute drive of Thompson's Point and Maine Mall.
Cambria Hotel Portland Downtown-Old Port
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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.