Search results; Over 1,000 places in Islesboro

Top guest favorite
Guesthouse in Islesboro
Islesboro Island Oceanfront Cottage
2 single beds
Jul 13 – 19
R37,471 ZAR for 6 nights
for 6 nights
5.0 out of 5 average rating, 10 reviews
Guest favorite
Home in Islesboro
Blue Moon Cottage
4 beds
Jul 1 – 6
R18,736 ZAR for 5 nights
for 5 nights
4.75 out of 5 average rating, 16 reviews
Guest favorite
Cottage in Islesboro
Islesboro Boathouse
Free cancellation
Jul 18 – 23
R52,994 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 101 reviews
Guest favorite
Home in Islesboro
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
Free cancellation
Sep 1 – 6
R57,812 ZAR for 5 nights, originally R78,078 ZAR
for 5 nights
5.0 out of 5 average rating, 19 reviews
Home in Islesboro
Surrounded by Water
7 beds
Aug 31 – Sep 7
R51,388 ZAR for 7 nights, originally R57,693 ZAR
for 7 nights
5.0 out of 5 average rating, 4 reviews
Top guest favorite
Apartment in Lincolnville
Ashgrove Garden on the Ocean
Free cancellation
May 31 – Jun 5
R12,847 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 62 reviews
Top guest favorite
Cottage in Islesboro
"The Dory" on Penobscot Bay, Mid-Coast Maine
3 beds
Jul 14 – 19
R35,330 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 28 reviews
Home in Islesboro
On the water in Ryder Cove
Free cancellation
Jul 1 – 6
R63,700 ZAR for 5 nights
for 5 nights
New place to stay
Home in Islesboro
Island Retreat
Free cancellation
Aug 3 – 8
R32,760 ZAR for 5 nights
for 5 nights
Home in Islesboro
Thundercloud - a Classic Maine Retreat
Free cancellation
Jul 28 – Aug 2
R42,974 ZAR for 5 nights
for 5 nights
Guest favorite
Home in Islesboro
Island Waterfront Cottage Islesboro, Maine
Free cancellation
Jul 12 – 18
R38,541 ZAR for 6 nights
for 6 nights
4.96 out of 5 average rating, 56 reviews
Villa in Islesboro
Bounty Cove Getaway and Private Nature Preserve
Free cancellation
Aug 22 – 27
R217,328 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 4 reviews
Home in Islesboro
Cottage on lovely island
Free cancellation
Jul 1 – 8
R39,612 ZAR for 7 nights
for 7 nights
New place to stay
Home in Islesboro
Islesboro Farmhouse
Free cancellation
Jul 1 – 6
R45,500 ZAR for 5 nights
for 5 nights
Guest favorite
Home in Islesboro
"The Gables" on Penobscot Bay, Mid-Coast Maine
Free cancellation
Aug 3 – 8
R34,259 ZAR for 5 nights
for 5 nights
4.89 out of 5 average rating, 71 reviews
Top guest favorite
Cottage in Northport
"Eagles Nest" Waterfront Cottage
2 beds
Aug 16 – 21
R61,023 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 12 reviews
Home in Islesboro
Charming 4 BR Farmhouse w/ Beach
Free cancellation
Aug 18 – 25
R82,435 ZAR for 7 nights
for 7 nights
4.84 out of 5 average rating, 19 reviews
Cottage in Islesboro
Beautiful Cottage on Island Bluff & Beach
5 beds
Sep 8 – 15
R79,223 ZAR for 7 nights
for 7 nights
5.0 out of 5 average rating, 7 reviews