Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
NEW
NEW
Experiences
Experiences, new
NEW
NEW
Services
Services, new
Start your search
Location
Homes in Chebeague Island
Check in / Check out
Any week
Guests
Add guests
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Type of place
Show map
Search results; Over 1,000 homes in Chebeague Island
Over 1,000 homes in Chebeague Island
Top guest favourite
Guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
1 bedroom
,
·
1 bed
,
·
1 private bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,226 SGD
Show price breakdown
for 5 nights
$1,226 SGD for 5 nights
,
·
4.98 out of 5 average rating, 192 reviews
4.98 (192)
Top guest favourite
Guest favourite
Home in Chebeague Island
Timber-Framed Island Home, Sleeps 8
5.0 out of 5 average rating, 11 reviews
5.0 (11)
,
·
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
13–18 Oct
13–18 Oct
$4,892 SGD
Show price breakdown
for 5 nights
$4,892 SGD for 5 nights
Guest house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
10–15 Sept
10–15 Sept
$1,345 SGD
Show price breakdown
for 5 nights
$1,345 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Cottage in Harpswell
Cottage with Ocean Views on Pott’s Point
4.97 out of 5 average rating, 39 reviews
4.97 (39)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
22–27 Aug
22–27 Aug
$2,398 SGD
Show price breakdown
for 5 nights
$2,398 SGD for 5 nights
Superhost
Superhost
Home in Chebeague Island
Post & beam house on three wooded acres
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
1–6 Aug
1–6 Aug
$3,311 SGD
Show price breakdown
for 5 nights
$3,311 SGD for 5 nights
Free cancellation
Home in Long Island
500Island
New place to stay
New
,
·
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
23–30 Aug
23–30 Aug
$11,024 SGD
Show price breakdown
for 7 nights
$11,024 SGD for 7 nights
Free cancellation
Superhost
Superhost
Cottage in Harpswell
The Red House - Waterfront cottage with AC!
New place to stay
New
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
28 Aug – 4 Sept
28 Aug – 4 Sept
$8,101 SGD
$7,470 SGD
Show price breakdown
for 7 nights
Weekly discount
Free cancellation
Top guest favourite
Guest favourite
Home in Harpswell
Sunset Stunner w/summer dock
4.97 out of 5 average rating, 32 reviews
4.97 (32)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
25–30 Oct
25–30 Oct
$2,816 SGD
Show price breakdown
for 5 nights
$2,816 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Guest house in Scarborough
Smith Cottage Higgins Beach
4.98 out of 5 average rating, 130 reviews
4.98 (130)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
20–25 Sept
20–25 Sept
$2,132 SGD
$1,713 SGD
Show price breakdown
for 5 nights
Top guest favourite
Guest favourite
Cabin in Freeport
Chickadee A-Frame
4.99 out of 5 average rating, 78 reviews
4.99 (78)
,
·
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
18–23 Oct
18–23 Oct
$2,588 SGD
Show price breakdown
for 5 nights
$2,588 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Home in Portland
Island Getaway, Short ferry ride to Portland
5.0 out of 5 average rating, 23 reviews
5.0 (23)
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
8–13 Sept
8–13 Sept
$2,034 SGD
Show price breakdown
for 5 nights
$2,034 SGD for 5 nights
Free cancellation
Home in Yarmouth
Oceanfront Cottage
2 bedrooms
2 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
2–9 Jan
2–9 Jan
$7,230 SGD
Show price breakdown
for 7 nights
$7,230 SGD for 7 nights
Free cancellation
Guest favourite
Guest favourite
Guest suite in Yarmouth
Ash + Timber | Forest Sauna Suite Near Portland
5.0 out of 5 average rating, 5 reviews
5.0 (5)
,
·
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
21–26 Sept
21–26 Sept
$2,358 SGD
Show price breakdown
for 5 nights
$2,358 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
4.96 out of 5 average rating, 357 reviews
4.96 (357)
,
·
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
10–15 Aug
10–15 Aug
$4,021 SGD
$3,440 SGD
Show price breakdown
for 5 nights
Free cancellation
Superhost
Superhost
Cottage in Harpswell
A charming 2-bedroom cottage with private beach.
4.67 out of 5 average rating, 3 reviews
4.67 (3)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
1–6 Nov
1–6 Nov
$1,476 SGD
$1,332 SGD
Show price breakdown
for 5 nights
Guest favourite
Guest favourite
Home in Georgetown
Serene Coveside Cottage
4.94 out of 5 average rating, 88 reviews
4.94 (88)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
2–7 Nov
2–7 Nov
$1,367 SGD
$1,226 SGD
Show price breakdown
for 5 nights
Free cancellation
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
New place to stay
New
,
·
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
12–17 Aug
12–17 Aug
$3,276 SGD
Show price breakdown
for 5 nights
$3,276 SGD for 5 nights
Free cancellation
Superhost
Superhost
Home in Raymond
Renovated New Waterfront Cottage on Crescent Lake!
New place to stay
New
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
27 Aug – 1 Sept
27 Aug – 1 Sept
$2,327 SGD
Show price breakdown
for 5 nights
$2,327 SGD for 5 nights
Free cancellation
Cottage in Portland
Spectacular Direct Oceanfront New Modern Home
4.7 out of 5 average rating, 20 reviews
4.7 (20)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$6,351 SGD
Show price breakdown
for 5 nights
$6,351 SGD for 5 nights
1
2
3
4
…
15