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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Browse Select Great Diamond Island Cottages

Little Miss Cottages
Relax in a serene outdoor space with Adirondack chairs, a picnic table, and a fire pit.

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (82)
"Place was great "
Little Miss Cottages
'osprey Cottage' South Freeport Home on Casco Bay!
Cottage (2 Bedrooms) | Interior

'osprey Cottage' South Freeport Home on Casco Bay!

3.0 star property
'osprey Cottage' South Freeport Home on Casco Bay!
Large Yard: Walkable Cottage in Old Orchard Beach!
Cottage (2 Bedrooms) | Interior

Large Yard: Walkable Cottage in Old Orchard Beach!

3.0 star property
Large Yard: Walkable Cottage in Old Orchard Beach!
Walk to Beach: Maine Home w/ Hot Tub & Deck!
House (5 Bedrooms) | Interior

Walk to Beach: Maine Home w/ Hot Tub & Deck!

3.0 star property
Walk to Beach: Maine Home w/ Hot Tub & Deck!
Charming Saco Home w/ Deck, 5 Mi to Beach!
House (3 Bedrooms) | Interior

Charming Saco Home w/ Deck, 5 Mi to Beach!

3.0 star property
10.0 out of 10, Exceptional, (1)
Charming Saco Home w/ Deck, 5 Mi to Beach!
Falmouth Vacation Rental On Highland Lake!
Enjoy meals in this well-equipped kitchen with a refrigerator, oven, and granite countertop.

Falmouth Vacation Rental On Highland Lake!

3.0 star property
6.0 out of 10, (1)
"The inside was clean and fine. When booking this place, the description mentioned a canoe, two kayaks and two paddle boards. However, due to the trees and brush on both sides of the dock, we were unable to put these in the water. It would have been extremely difficult to lift any of these items over the dock and into one foot of water. It would have been just as hard taking them out. "
Falmouth Vacation Rental On Highland Lake!
Historic Casco Bay Home on Great Diamond Island
Relax in this serene outdoor seating area with a park view, featuring a round table and comfortable seating for two.

Historic Casco Bay Home on Great Diamond Island

3.0 star property
Historic Casco Bay Home on Great Diamond Island
Near Portland trails: Walkable Apartment w/ Deck
Relax in a cozy seating area with a sofa, armchairs, and a TV.

Near Portland trails: Walkable Apartment w/ Deck

3.0 star property
Near Portland trails: Walkable Apartment w/ Deck
Walk to OOB Pier: Family-friendly Home w/ Hot Tub!
House (3 Bedrooms) | Interior

Walk to OOB Pier: Family-friendly Home w/ Hot Tub!

3.0 star property
Walk to OOB Pier: Family-friendly Home w/ Hot Tub!
'heron Cottage' on Casco Bay w/ Deck & Boat Dock!
Cottage (1 Bedroom) | Interior

'heron Cottage' on Casco Bay w/ Deck & Boat Dock!

3.0 star property
'heron Cottage' on Casco Bay w/ Deck & Boat Dock!
Sebago Lake Gem on Private Cove w/ Boat Dock!
Relax in a spacious living area with sofas, armchairs, and a fireplace, perfect for socializing and taking in the view.

Sebago Lake Gem on Private Cove w/ Boat Dock!

3.0 star property
Sebago Lake Gem on Private Cove w/ Boat Dock!
Charming Orr's Island Cottage w/ Ocean Views
Relax in this inviting living area with a high ceiling, featuring a dining table, sofa, and stone fireplace.

Charming Orr's Island Cottage w/ Ocean Views

3.0 star property
Charming Orr's Island Cottage w/ Ocean Views
Waterfront Sebago Lake Cottage W/dock + Beach
Relax on the lakeside deck with comfortable seating and enjoy the serene surroundings.

Waterfront Sebago Lake Cottage W/dock + Beach

3.0 star property
Waterfront Sebago Lake Cottage W/dock + Beach
Charming Retreat w/ Deck ~ 4 Mi From Casco Bay!
House (4 Bedrooms) | Interior

Charming Retreat w/ Deck ~ 4 Mi From Casco Bay!

3.0 star property
Charming Retreat w/ Deck ~ 4 Mi From Casco Bay!
Charming Pine Point Cottage - 2 Blocks to Ocean!
Cottage (3 Bedrooms) | Interior

Charming Pine Point Cottage - 2 Blocks to Ocean!

3.0 star property
Charming Pine Point Cottage - 2 Blocks to 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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Frequently asked questions

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Booking a cottage in Great Diamond Island is as simple as clicking on your travel dates and selecting an ideal place for outdoor relaxation and recreation. From luxurious retreats to inexpensive stays and cottages that come with amenities like laundry facilities, Expedia has something for all styles and tastes. As for terrific deals? We've got them too!
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Expedia can help you locate cheap cottages in Great Diamond Island. To book a fantastic stay in a couple of quick clicks, try out our handy filter tool to refine your search by amenities, star rating and budget.