Great Diamond Island Beach Vacations

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4 Night Beach vacations in Great Diamond Island

Price found within the past 48 hours. Click for updated prices.
Inn at Diamond Cove
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Find your perfect Great Diamond Island beach vacation

How do I book the best Great Diamond Island beach vacation packages?

Life’s a beach when you dive into our brilliant Great Diamond Island beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Great Diamond Island?

A rental steps from the shore creates an amazingly affordable Great Diamond Island beach vacation. Seaside sojourns during low season start from $971. Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in Great Diamond Island?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Great Diamond Island beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Great Diamond Island vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Great Diamond Island beach vacation deals?

Sort your search results by deals to delight in amazing Great Diamond Island beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Great Diamond Island beach trip with free cancellation and/or flexible dates?

Just like the Great Diamond Island tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Great Diamond Island beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Great Diamond Island. (OK, maybe not that last part.)

Top Beach Great Diamond Island Hotels

Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
22 Mckinley Court, Great Diamond Island Portland ME
  • 40 min drive from Old Orchard Beach Pier
Relax at this hotel and get ready to lounge by the shoreline in Portland, as you'll be not far from the beach. Amenities at Inn at Diamond Cove include 2 restaurants, ...
8.8/10 Excellent! (195 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...
"Beautiful room, comfortable bed unique property!"

Reviewed on Oct 8, 2025

Inn at Diamond Cove
Cozy townhouse minutes from downtown Portland on a car free island

Cozy townhouse minutes from downtown Portland on a car free island

Portland ME
  • 40 min drive from Old Orchard Beach Pier
Book a stay at this family-friendly vacation home in Portland. Enjoy a fitness center, laundry facilities, and tennis courts. Popular attractions Portland Head ...
9.4/10 Exceptional! (3 reviews)
"We had a lovely weekend on Great Diamond Island! Having lived on the island, I felt right at home!"

Reviewed on Oct 14, 2025

Cozy townhouse minutes from downtown Portland on a car free island
Historic Officer's Quarters House on Great Diamond Island Near Beaches

Historic Officer's Quarters House on Great Diamond Island Near Beaches

Portland ME
  • 39 min drive from Old Orchard Beach Pier
Make the most of this fantastic location, as you'll be near the beach with a vacation at this vacation home.
10/10 Exceptional! (2 reviews)

Travelers like: close to beach, pool

Fall Wedding
"Loved the 3rd floor room, great for kids!"

Reviewed on Oct 13, 2023

Historic Officer's Quarters House on Great Diamond Island Near Beaches
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.