Search results; Over 1,000 places in Islesboro

Prices include all fees
Guest favorite
Cottage in Islesboro
Islesboro Boathouse
1 bed
May 22 – 27
ﺩ.ﺇ10,654 for 5 nights
for 5 nights
5.0 out of 5 average rating, 99 reviews
Top guest favorite
Guesthouse in Islesboro
Milk House
1 bed
May 17 – 22
ﺩ.ﺇ2,820 for 5 nights
for 5 nights
4.96 out of 5 average rating, 24 reviews
Top guest favorite
Cottage in Islesboro
"The Dory" on Penobscot Bay, Mid-Coast Maine
3 beds
May 18 – 23
ﺩ.ﺇ6,350 for 5 nights
for 5 nights
5.0 out of 5 average rating, 27 reviews
Home in Islesboro
Cottage on lovely island
Free cancellation
Jun 5 – 10
ﺩ.ﺇ5,812 for 5 nights
for 5 nights
New place to stay
Top guest favorite
Guesthouse in Islesboro
Islesboro Island Oceanfront Cottage
2 single beds
May 18 – 23
ﺩ.ﺇ6,350 for 5 nights
for 5 nights
5.0 out of 5 average rating, 10 reviews
Guest favorite
Home in Islesboro
"The Gables" on Penobscot Bay, Mid-Coast Maine
5 beds
May 19 – 24
ﺩ.ﺇ6,564 for 5 nights
for 5 nights
4.89 out of 5 average rating, 71 reviews
Cottage in Islesboro
Sweet, three bedroom cape on peaceful cove
3 beds
May 17 – 22
ﺩ.ﺇ7,319 for 5 nights
for 5 nights
4.93 out of 5 average rating, 28 reviews
Cottage in Islesboro
Beautiful Cottage on Island Bluff & Beach
5 beds
May 28 – Jun 4
ﺩ.ﺇ13,561 for 7 nights
for 7 nights
5.0 out of 5 average rating, 7 reviews
Guest favorite
Home in Islesboro
Island Waterfront Cottage Islesboro, Maine
Free cancellation
Jul 12 – 18
ﺩ.ﺇ7,749 for 6 nights
for 6 nights
4.96 out of 5 average rating, 56 reviews
Home in Islesboro
Island Retreat
3 beds
May 18 – 23
ﺩ.ﺇ6,587 for 5 nights
for 5 nights
Guest favorite
Room in Islesboro
Stay with EllenHosting for 11 years,
Islesboro Island Getaway. Private BR.
May 17 – 22
ﺩ.ﺇ2,476 for 5 nights
for 5 nights
5.0 out of 5 average rating, 9 reviews
Home in Lincolnville
Cozy Retreat in Ducktrap Village
Free cancellation
May 29 – Jun 3
ﺩ.ﺇ5,338 for 5 nights
for 5 nights
New place to stay
Villa in Islesboro
Bounty Cove Getaway and Private Nature Preserve
Free cancellation
May 23 – 28
ﺩ.ﺇ40,467 for 5 nights
for 5 nights
5.0 out of 5 average rating, 4 reviews
Home in Islesboro
Charming 4 BR Farmhouse w/ Beach
7 beds
May 18 – 25
ﺩ.ﺇ16,574 for 7 nights
for 7 nights
4.84 out of 5 average rating, 19 reviews
Home in Islesboro
Surrounded by Water
7 beds
Aug 18 – 25
ﺩ.ﺇ15,067 for 7 nights
for 7 nights
5.0 out of 5 average rating, 4 reviews
Home in Islesboro
Charming Seaside Island Retreat
Free cancellation
Jun 7 – 12
ﺩ.ﺇ9,362 for 5 nights
for 5 nights
Home in Islesboro
FoxGlove Farm on Islesboro
5 beds
May 20 – 25
ﺩ.ﺇ9,750 for 5 nights
for 5 nights
Home in Islesboro
Island Home
6 beds
May 24 – 31
ﺩ.ﺇ13,130 for 7 nights
for 7 nights