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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec

Cottages in Great Diamond Island

Private Contemporary Artist's Tree House on two acres with perennial gardens.
Exterior

Private Contemporary Artist's Tree House on two acres with perennial gardens.

10.0 out of 10, Exceptional, (48)
"Beautiful, fun space. Very comfortable, and accommodating. Great location and hosts!"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Exterior

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (7)
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Exterior

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

9.8 out of 10, Exceptional, (60)
"My stay at the cottage was exactly what I needed, it’s an updated beachy vibe and excellent use of every space including some rainy day puzzles and books! The small fenced in yard was perfect for the furry family members, and you cant beat the location, such a close walk to the beach, and just far enough away from the busy OOB hustle! Would definitely stay again! "
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
WATERFRONT ON PETTENGILL POND
Exterior

WATERFRONT ON PETTENGILL POND

9.6 out of 10, Exceptional, (4)
"My kids and I loved our stay at the pond. We enjoyed kayaking and floating in the peaceful setting. "
WATERFRONT ON PETTENGILL POND
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
Terrace/patio

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (39)
"The view is beautiful and has everything you need "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
Large 2BD cottage 10 min to Pier & Beach Pets ok
Exterior

Large 2BD cottage 10 min to Pier & Beach Pets ok

9.0 out of 10, Wonderful, (36)
"Easy walk into the board walk shopping area ! Private parking and owner was readily available for any issues or concerns....gas station and lobster pound close enough i walked to pick us up dinner....5 lobster fresh cooked $45 and we're still steaming hot by time i walked back to the house"
The price is AED 1,084
AED 1,686 total
includes taxes & fees
9 Oct - 10 Oct
Large 2BD cottage 10 min to Pier & Beach Pets ok
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Exterior

Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC

9.4 out of 10, Exceptional, (9)
"We recently rented this for a quick family vacation and it exceeded our expectations. Can't wait to go back next summer!"
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Property grounds

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout

9.4 out of 10, Exceptional, (88)
"The setting was absolutely beautiful. Shawn was extremely responsive and went out of his away to be accommodating. Would highly recommend!"
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!
Terrace/patio

Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!

9.8 out of 10, Exceptional, (34)
"Clean, cute cottage for four on a steep waterfront lot with a beautiful vista. Nice kitchen for exended stay. Great fireplace."
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!
Coastal Charm 2 Bedroom Beach Cottage ~Just Steps to the Beach in Kinney Shores~
Exterior

Coastal Charm 2 Bedroom Beach Cottage ~Just Steps to the Beach in Kinney Shores~

10.0 out of 10, Exceptional, (5)
Coastal Charm 2 Bedroom Beach Cottage ~Just Steps to the Beach in Kinney Shores~
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat
Terrace/patio

Ocean Watch - Relax and let the ocean sweep you away at this charming retreat

8.8 out of 10, Excellent, (21)
"Very beautiful and easy to communicate with the property management "
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat
Brand new charming cottage next to the pristine sandy beaches of Biddeford Pool
Exterior

Brand new charming cottage next to the pristine sandy beaches of Biddeford Pool

10.0 out of 10, Exceptional, (4)
"It was a great stay. The house is in wonderful condition. The hosts were very helpful and our stay was relaxing and enjoyable. "
Brand new charming cottage next to the pristine sandy beaches of Biddeford Pool
Oceanfront Escape: Deck & Granite Steps to Shore
Property grounds

Oceanfront Escape: Deck & Granite Steps to Shore

9.4 out of 10, Exceptional, (3)
"Everything was beautiful and we loved our stay!"
Oceanfront Escape: Deck & Granite Steps to Shore
Cute cottage only a 10 min walk to the beach.
Exterior

Cute cottage only a 10 min walk to the beach.

10.0 out of 10, Exceptional, (12)
"Our stay was perfect. The house is really cute and well located for going to the beach."
Cute cottage only a 10 min walk to the beach.
Updated Long Island Maine Cottage
Exterior

Updated Long Island Maine Cottage

10.0 out of 10, Exceptional, (6)
"Great location. Comfortable living room. Well stocked kitchen. Great communication with owner."
Updated Long Island Maine Cottage
2 bedroom cottage
Smart TV

2 bedroom cottage

8.8 out of 10, Excellent, (8)
"quiet, clean, short walk to beach"
2 bedroom cottage
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
Property grounds

Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings

9.8 out of 10, Exceptional, (52)
"We had a wonderful time at this house! It’s perfectly situated by the beach, just a stone’s throw away from the charming village of Biddeford Pool. You can even grab some fresh, steamed lobster at the grocery store there. The house offers breathtaking views of the sunset and the bay, and there’s plenty of great outdoor space for relaxation. Parking is also a breeze. The host is incredibly friendly and responsive, making our stay even more enjoyable. We even had a travel massage for our...
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path
Exterior

Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path

9.0 out of 10, Wonderful, (78)
"Loved how close it was to the beach.. very sweet little cottage."
Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
Exterior

Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.

9.6 out of 10, Exceptional, (40)
"We had a great time! We never saw the tide drain completely out to forage though, I was looking forward to that. The location is perfect with a lovely deck. Bring bug spray, mosquitoes are super thick, assuming from all of the rain we had. The pull out sofa is not really usable due to a bar at the top that sticks in your ribs. Kitchen was fully equipped and loved having a dishwasher. Owners and/or management were very responsive with a couple of issues that arose. We unfortunately had to leave a...
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
Sea Bisquit Cottage by the Ocean
Exterior

Sea Bisquit Cottage by the Ocean

9.4 out of 10, Exceptional, (19)
"The cottage is great! It's so close to the beach and very cozy. The mattress sinks a little in the middle so we slept on the futon, which was very comfortable. "
Sea Bisquit Cottage by the Ocean
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

Inn at St John Portland In-Town

Inn at St John Portland In-Town

10/10 Excellent
"Hotel in great old Victorian house."
Stacia 1-night trip
Posted 14 hours ago
Inn at St John Portland In-Town

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