Photo by Robbie Martin

Search Guest Houses in Great Diamond Island

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The Rebekah Inn

2.5 star property
8.8 out of 10, Excellent, (74)
"Nice place to stay with good rates and right by the water. Very clean "
The Rebekah Inn

Beaches, Trails, Hammock, Fire-Pit, Peaceful!

6.0 out of 10, (2)
"This cute little carriage house was built into the passageway behind the main house and the barn. It comfortably fit our party of 3 adults with a nice size kitchen, a single bathroom, and spacious seating areas both inside and out. Our flight was delayed, and when we arrived, there was yogurt and fruit in the fridge waiting for us. There is a stand selling ice cream, burgers, and lobster rolls within walking distance, and the Cape Elizabeth beach is a short drive away. Lovely stay!"
Beaches, Trails, Hammock, Fire-Pit, Peaceful!

Cozy 3BR Beach House by the Sea

2.0 star property
8.0 out of 10, Very good, (1)
"Close to everything "
Cozy 3BR Beach House by the Sea

Maine Artist Retreat

5.8 out of 10, (6)
"After the reservation was confirmed, the host canceled on us just three days before the trip — then refused to refund us until VRBO customer service stepped in. Avoid this property!"
Maine Artist Retreat
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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Other property types in Great Diamond Island

Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

9.8 out of 10, Exceptional, (115)
"Very relaxing getaway."
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (98)
"Great oceanfront location for a relaxing girls getaway. We enjoyed walking the beach and collecting shells. Great location to start from to see other cities in the area. Best part was watching the sunrise in the morning from the balcony. "
Gorgeous ocean-front home with stunning beach views

Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist

10.0 out of 10, Exceptional, (35)
"What a great place! Located in the arts district, this refurbished brownstone has every modern convenience within walking distance of restaurants and museums. Windows on both sides of the apartment provide street views, one active and bustling, one quiet with a view of Casco Bay and sunrises. And the rooftop patio is a dream - we loved being part of Portland history with an up close view of the florist's ad mural!"
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.