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Holiday Homes in Great Diamond Island

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Great Diamond Island and around

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Kitchen area with microwave, toaster, refrigerator, and sink.

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

9.8 out of 10, Exceptional, (50)
"We enjoyed ourselves very much! Close to everything we wanted to do. Would stay again."
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
4-bedroom vacation home steps to Old Orchard Beach Pier
Stroll along the pier, taking in the serene views of the ocean and surrounding landscape.

4-bedroom vacation home steps to Old Orchard Beach Pier

10.0 out of 10, Exceptional, (12)
"Mitchells home was PERFECT.Always quick to communicate and very accommodating. If you are looking for a great place to stay I cant say enough good things. Well stocked he has thought of everything people need when away. He even has games to play which was a nice surprise. You wont regret staying bere! Thanks again so much Mitchell!!!"
4-bedroom vacation home steps to Old Orchard Beach Pier
Beach House ∆ Prime Location ∆ Steps to the Ocean
Cozy attic bedroom with a large bed, nightstands, and a window above.

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (44)
"The house is in a wonderful location with great views of the ocean from several rooms. The listing photos really do tell the story of this beautiful home. The beach is just a few steps away from the property. Attention to detail was obviously put in to ensure a wonderful guest experience. The home is very clean, there are practical amenities throughout (4 smart TV’s), and our host was super communicative and accommodating. Portland & Saco being a short drive away is just icing on the cake. Can’t...
The price is €737
includes taxes & fees
31 Aug - 1 Sept
Beach House ∆ Prime Location ∆ Steps to the Ocean
Shady Potts Point Cottage Cooled by Ocean Breezes
Enjoy a peaceful stay in this charming house with a porch, surrounded by a lush lawn and a majestic tree.

Shady Potts Point Cottage Cooled by Ocean Breezes

9.8 out of 10, Exceptional, (83)
"Great stay in very clean house in a very quiet ocean side community. Perfect getaway!"
Shady Potts Point Cottage Cooled by Ocean Breezes
Sunny Modern Oasis in Portland’s Trendy East End
Relax on the spacious deck with a table and chairs, taking in views of the surrounding greenery.

Sunny Modern Oasis in Portland’s Trendy East End

10.0 out of 10, Exceptional, (53)
"This apartment was very clean, modern, and fairly private, located on a quite street, but still close enough to walk to shops, cafes, breweries. Only about half a mile from downtown. Would definitely stay again!"
Sunny Modern Oasis in Portland’s Trendy East End
On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing.
Enjoy a serene beach experience with gentle waves lapping against the shore.

On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing.

10.0 out of 10, Exceptional, (63)
"Perfect size home for a small group (we had 5). Great location for day trips to Bath, Boothbay, Freeport, and more. Host is super friendly and attentive! We loved being able to take advantage of the Resort restaurant and grounds. "
On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing.
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Stunning two-story home surrounded by lush greenery and trees, featuring a charming front porch and symmetrical facade.

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (76)
"We had a great stay! Amazing weather and plenty of lobster."
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Beachfront, Just steps and you're on the beach!
On the beach

Beachfront, Just steps and you're on the beach!

10.0 out of 10, Exceptional, (1)
"We loved our stay at the cottage. It was exceptionally clean and quiet. "
Beachfront, Just steps and you're on the beach!
Elegant and efficient Island home 4 miles from downtown Portland
Outdoor dining

Elegant and efficient Island home 4 miles from downtown Portland

Elegant and efficient Island home 4 miles from downtown Portland
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Enjoy meals in the kitchen with a stove and dining area featuring a table and chairs.

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

2.0 star property
9.0 out of 10, Wonderful, (8)
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
Relax in this stylish living room with a high ceiling, comfortable sofa, and flat-screen TV.

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

8.2 out of 10, Very good, (54)
"We had a large group and had more than enough beds and plenty of space to hang out. Would recommend for a big group or a family looking to spread out!"
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
The Good Bones Abode
Property grounds

The Good Bones Abode

10.0 out of 10, Exceptional, (2)
"We enjoyed this well kept property with beautiful gardens. It was very pet friendly with a nice back yard area. We cooked steak on the grill one night."
The Good Bones Abode
Fantastic Waterfront Views
Relax in this serene bedroom with a large bed, a cozy reading nook, and a deck overlooking the forest.

Fantastic Waterfront Views

9.8 out of 10, Exceptional, (7)
"Our favorite part about our stay at this location was being able to look out the many sliding door windows to see the ocean view. It was a very relaxing place to stay. "
The price is €560
includes taxes & fees
31 Aug - 1 Sept
Fantastic Waterfront Views
Enchanting 3BR Farmhouse Retreat Nature Getaway
Enjoy cooking in this well-equipped kitchen with oven, microwave, and refrigerator.

Enchanting 3BR Farmhouse Retreat Nature Getaway

10.0 out of 10, Exceptional, (3)
"We really enjoyed this property. It was very clean, and very comfortable. We will visit again. "
Enchanting 3BR Farmhouse Retreat Nature Getaway
Large, light filled 4 bedroom house - walk to ocean and ferry
Relax on the porch with a round table and two Adirondack chairs, surrounded by lush greenery.

Large, light filled 4 bedroom house - walk to ocean and ferry

10.0 out of 10, Exceptional, (32)
"Comfortable place to stay and enjoy time with family. We enjoyed exploring Peaks Island and Portland. Everything we needed."
Large, light filled 4 bedroom house - walk to ocean and ferry
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!
Fully equipped kitchen with dishwasher, oven, refrigerator, sink, and kettle.

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

10.0 out of 10, Exceptional, (142)
"This was our second stay at Beth’s home, and it certainly won’t be the last (as long as she’s willing to have us!) Everything is absolutely perfect. Beth is a thoughtful host, the location is perfect and the home is beautiful - you can’t go wrong!"
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!
Spacious 4-bedroom house located in the heart of Portland, ME.
Interior

Spacious 4-bedroom house located in the heart of Portland, ME.

The price is €877
includes taxes & fees
1 Sept - 2 Sept
Spacious 4-bedroom house located in the heart of Portland, ME.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Relax in style with ocean views from the spacious balcony, surrounded by a grassy area perfect for unwinding in Adirondack chairs.

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

10.0 out of 10, Exceptional, (222)
"We enjoyed everything about our place!"
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Modern Getaway by the Sea
Fridge, microwave, oven, stovetop

Modern Getaway by the Sea

The price is €512
includes taxes & fees
11 Aug - 12 Aug
Modern Getaway by the Sea
Quaint Cottage Vacation
Stroll through the charming garden, surrounded by a white picket fence, and enjoy the covered porch with a bench.

Quaint Cottage Vacation

9.0 out of 10, Wonderful, (28)
"Had a great time!!"
Quaint Cottage Vacation
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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Top Great Diamond Island Hotel Reviews

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

10/10 Excellent
"The staff was very helpful and pleasant. The breakfast was ok, the pool is small but a nice feature for our kids. Would stay again overall would definitely stay here again."
Haley 1-night trip
Posted 1 day ago
Days Inn by Wyndham Airport/Maine Mall