Book Holiday Homes in Great Diamond Island

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Featured Holiday Homes in Great Diamond Island

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

2 out of 5
Scarborough
With a stay at this vacation home in Scarborough (Grand Beach), you'll be within a 5-minute drive of Old Orchard Beach Pier and Old Orchard Beach.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
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
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Old Orchard Beach
The price is AU$2,317 per night from 8 Sept to 9 Sept
AU$2,317
8 Sept - 9 Sept
includes taxes & fees
When you stay at this vacation home in Old Orchard Beach, you'll be on the beach, just steps from Old Orchard Beach and 15 minutes by foot from Old Orchard Beach ...
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
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5 HOUSES AWAY FROM BEACH - DISCOUNTED FOR 08/16-08/23,08/23-08/30 AND SEPTEMBER

5 HOUSES AWAY FROM BEACH - DISCOUNTED FOR 08/16-08/23,08/23-08/30 AND SEPTEMBER

Old Orchard Beach
A stay at this vacation home places you in the heart of Old Orchard Beach, just a 3-minute walk from Old Orchard Beach and within a 5-minute drive of Old Orchard ...
5 HOUSES AWAY FROM BEACH - DISCOUNTED FOR 08/16-08/23,08/23-08/30 AND SEPTEMBER
Full sized home

Full sized home

Harpswell
The price is AU$572 per night from 15 Sept to 16 Sept
AU$572
15 Sept - 16 Sept
includes taxes & fees
With a stay at this vacation home in Harpswell, you'll be by the sea, just steps from Casco Bay and a 3-minute drive from Ash Cove Pottery.
Full sized home
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
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!

5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!

Portland
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.
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with 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
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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.

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

Holiday houses in Great Diamond 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 Great Diamond 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 Great Diamond Island adventures, obvs.

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

Great Diamond Island Holiday Homes essential information

Accommodation
599 Holiday Homes
Lowest Price
AU$141
Highest Price
AU$2,317
Popular accommodation
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough, Beautiful house on the Harpswell Peninsula over looking Casco Bay, Sensational Beachfront Property Old Orchard Beach, with indoor elevator, 5 HOUSES AWAY FROM BEACH - DISCOUNTED FOR 08/16-08/23,08/23-08/30 AND SEPTEMBER, Full sized home, Beautiful Oceanfront House- Stunning Water Views, 5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views! , New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach, Camp Forever cottage

Top trending hotels in Great Diamond Island

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$192 per night from 30 Sept to 1 Oct
AU$192
30 Sept - 1 Oct
includes taxes & fees
With a stay at Fireside Inn & Suites Portland in Portland (Nasons Corner), you'll be a 1-minute drive from Happy Wheels Skate Center and 7 minutes from Maine ...
Fireside Inn & Suites Portland
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is AU$141 per night from 6 Oct to 7 Oct
AU$141
6 Oct - 7 Oct
includes taxes & fees
With a stay at Germaine Inn South Portland in South Portland, you'll be a 4-minute drive from Maine Mall and 6 minutes from Thompson's Point.
Germaine Inn South Portland
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$215 per night from 8 Sept to 9 Sept
AU$215
8 Sept - 9 Sept
includes taxes & fees
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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La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$270 per night from 7 Sept to 8 Sept
AU$270
7 Sept - 8 Sept
includes taxes & fees
Located in Portland, La Quinta Inn & Suites by Wyndham Portland DT/Maine Med is a 5-minute walk from Portland Exposition Building and 5 minutes by foot from ...
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
Don't see what you're looking for?
See all available properties in Great Diamond 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.