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Search Cottages in Great Diamond Island from CA $173

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Check prices for these dates

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Aug 29 - Aug 31
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Sep 5 - Sep 7
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Sep 19 - Sep 21
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Oct 17 - Oct 19

Browse Select Great Diamond Island Cottages

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

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

10.0 out of 10, Exceptional, (5)
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (7)
"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
WATERFRONT ON PETTENGILL POND
Property grounds

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
Little Miss Cottages
Property grounds

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (87)
"Cute and tidy cottage, easy walk to beautiful beach."
Little Miss Cottages
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Outdoor spa tub

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

10.0 out of 10, Exceptional, (43)
"Beautiful, fun space. Very comfortable, and accommodating. Great location and hosts!"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room
Terrace/patio

THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room

10.0 out of 10, Exceptional, (53)
"Beautiful views from a charming cottage with kind neighbors. Eclectic styled home which we enjoyed. Would stay again!!"
THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room
Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path
Dining

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

9.2 out of 10, Wonderful, (75)
"Loved how close it was to the beach.. very sweet little cottage."
Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path
Cozy Cottage with stunning views of Stover's Cove.
Interior

Cozy Cottage with stunning views of Stover's Cove.

9.8 out of 10, Exceptional, (7)
"We loved our time at the Cozy Cottage. They have the space well stocked with laundry detergent, dish soap, and even toiletries! All the communication was smooth and fast replies. I would recommend staying here if you are visiting Harpswell! "
Cozy Cottage with stunning views of Stover's Cove.
Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront
Microwave, oven, stovetop, dishwasher

Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront

10.0 out of 10, Exceptional, (1)
Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront
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, (34)
"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 CA $173
CA $345 total
includes taxes & fees
Sep 1 - Sep 2
Large 2BD cottage 10 min to Pier & Beach Pets ok
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, (86)
"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
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
Marina

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

9.8 out of 10, Exceptional, (51)
"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
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, (39)
"Peaceful, beautiful property. Perfect for our honeymoon. Highly recommend this place and Gurnet Trading Post for seafood!"
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
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

8.6 out of 10, Excellent, (18)
"Very relaxing."
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (33)
"Have stayed here two times over the years and it’s a great place for small families. We thoroughly enjoyed our recent visit."
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!
Cute cottage only a 10 min walk to the beach.
Beach

Cute cottage only a 10 min walk to the beach.

10.0 out of 10, Exceptional, (11)
"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.
Oceanfront Escape: Deck & Granite Steps to Shore
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Oceanfront Escape: Deck & Granite Steps to Shore

9.0 out of 10, Wonderful, (2)
"Everything was beautiful and we loved our stay!"
Oceanfront Escape: Deck & Granite Steps to Shore
2 bedroom cottage
Smart TV

2 bedroom cottage

9.2 out of 10, Wonderful, (5)
"quiet, clean, short walk to beach"
2 bedroom cottage
Cute 2+ Bedroom Cottage
Fridge, microwave, oven, stovetop

Cute 2+ Bedroom Cottage

9.6 out of 10, Exceptional, (18)
"Returned this year for our 2nd stay. Clean, comfortable and quiet. Will book again!"
Cute 2+ Bedroom Cottage
Sea Bisquit Cottage by the Ocean
Sun loungers, beach towels

Sea Bisquit Cottage by the Ocean

9.4 out of 10, Exceptional, (17)
"Cute cozy cottage a few minutes walk from quiet Old Orchard/Pine Point beach. "
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

Comfort Inn Airport

Comfort Inn Airport

10/10 Excellent
"Staff were very nice and transportation to airport was excellent. Room was spotless."
Linda 1-night trip
Posted 5 hours ago
Comfort Inn Airport