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Browse Select Chebeague Island Cottages

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (83)
"Place was great "
Little Miss Cottages

Peaceful Maine Home w/ Patio: Ocean Inlet Getaway!

3.0 star property
Peaceful Maine Home w/ Patio: Ocean Inlet Getaway!

'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!

3.0 star property
Large Yard: Walkable Cottage in Old Orchard Beach!

Ocean Inlet Cottage w/ Deck & Grill!

3.0 star property
Ocean Inlet Cottage w/ Deck & Grill!

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

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

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!

Riverfront Topsham Home ~ 28 Mi to Portland!

3.0 star property
2.0 out of 10, (1)
"The place was infested with bugs crawling on the walls and floors. The bedsheets had dead bugs on them when the top covers were removed. Bedsheets also had stains on them. There were no fans or a/c. We bought fans and left them there. The kitchen had some kind of fungus growing in it. All the ceilings had webs with spiders in it. Floors were not washed. All outdoor furniture were covered in mold. Would not recommend this place. "
Riverfront Topsham Home ~ 28 Mi to Portland!

Sun-soaked Coastal Cottage w/ Deck + Walk to Beach

3.0 star property
10.0 out of 10, Exceptional, (1)
"This is a very beautiful and spacious cottage with views of the ocean, which is across the street and one short block down. It’s half a mile from the pier, far enough to be a little quieter but close enough to be easily walkable. We would definitely stay here again. "
Sun-soaked Coastal Cottage w/ Deck + Walk to Beach

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

3.0 star property
Near Portland trails: Walkable Apartment w/ Deck

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

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

Kennebec River Cottage; 1/4 Mi to Boat Ramp!

3.0 star property
Kennebec River Cottage; 1/4 Mi to Boat Ramp!

Historic Bath Home, Walk to Waterfront Park!

3.0 star property
Historic Bath Home, Walk to Waterfront Park!

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

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

Waterfront Gray Home w/ Furnished Deck & Fire Pit!

3.0 star property
Waterfront Gray Home w/ Furnished Deck & Fire Pit!

Charming Orr's Island Cottage w/ Ocean Views

3.0 star property
Charming Orr's Island Cottage w/ Ocean Views

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!

3.0 star property
Charming Pine Point Cottage - 2 Blocks to Ocean!

Spacious Portland Home: Walk Downtown!

3.0 star property
Spacious Portland Home: Walk Downtown!
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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