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 Cumberland County
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
Over 1,000 homes
Top guest favourite
Guest favourite
Home in Cumberland
Forest Lake Cottage
2 bedrooms
,
·
2 beds
,
·
2 private bathrooms
6–11 Oct
6–11 Oct
$1,812 SGD
$1,568 SGD
Show price breakdown
for 5 nights
,
·
4.96 out of 5 average rating, 72 reviews
4.96 (72)
Superhost
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
1.5 bathrooms
1.5 bathrooms
5–10 Sept
5–10 Sept
$3,636 SGD
$3,209 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Superhost
Superhost
Flat in New Gloucester
Cozy Winter Suite & Hot Tub
1 bedroom
1 bedroom
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
28 Aug – 2 Sept
28 Aug – 2 Sept
$1,282 SGD
Show price breakdown
for 5 nights
$1,282 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 62 reviews
4.92 (62)
Top guest favourite
Guest favourite
Guest suite in Freeport
Studio Apartment in Freeport
3 beds
3 beds
,
·
1 bathroom
1 bathroom
22–27 Sept
22–27 Sept
$1,536 SGD
Show price breakdown
for 5 nights
$1,536 SGD for 5 nights
4.98 out of 5 average rating, 135 reviews
4.98 (135)
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
28 Aug – 2 Sept
28 Aug – 2 Sept
$3,669 SGD
$3,241 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
31 Aug – 5 Sept
31 Aug – 5 Sept
$1,996 SGD
Show price breakdown
for 5 nights
$1,996 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Top guest favourite
Guest favourite
Cottage in Pownal
Dreamy Post&Beam Hideaway Near Portland & Freeport
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
25–30 Oct
25–30 Oct
$2,252 SGD
Show price breakdown
for 5 nights
$2,252 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 474 reviews
4.99 (474)
Top guest favourite
Guest favourite
Tiny home in Limerick
The Fish Bowl-Waterfront Tiny House
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
19–24 Oct
19–24 Oct
$1,108 SGD
Show price breakdown
for 5 nights
$1,108 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Top guest favourite
Guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
12–17 Sept
12–17 Sept
$3,352 SGD
$2,801 SGD
Show price breakdown
for 5 nights
Free cancellation
4.96 out of 5 average rating, 366 reviews
4.96 (366)
Top guest favourite
Guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
21–26 Aug
21–26 Aug
$1,213 SGD
Show price breakdown
for 5 nights
$1,213 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 198 reviews
4.98 (198)
Guest favourite
Guest favourite
Home in Portland
Charming house near downtown and comfortable.
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
4–9 Oct
4–9 Oct
$2,325 SGD
$2,044 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Top guest favourite
Guest favourite
Cabin in Oxford
Glamping Cabin with Hot Tub and Onsite Sauna
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,717 SGD
Show price breakdown
for 5 nights
$1,717 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Guest favourite
Guest favourite
Home in Naples
LUX Designer Private Waterfront Hot Tub - Secluded
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
21–26 Sept
21–26 Sept
$6,361 SGD
$5,748 SGD
Show price breakdown
for 5 nights
Free cancellation
4.98 out of 5 average rating, 194 reviews
4.98 (194)
Guest favourite
Guest favourite
Flat in Lisbon Falls
Charming Victorian farmhouse 1880's bedrooms-2
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
24–29 Oct
24–29 Oct
$1,026 SGD
Show price breakdown
for 5 nights
$1,026 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 546 reviews
4.94 (546)
Top guest favourite
Guest favourite
Home in Raymond
Lake front home on Little Sebago
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
1.5 bathrooms
1.5 bathrooms
7–12 Sept
7–12 Sept
$3,982 SGD
$2,666 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Guest favourite
Guest favourite
Home in Naples
Trickey Moose Family Retreat | Fire Pit Kayaks
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$3,573 SGD
$3,011 SGD
Show price breakdown
for 5 nights
Free cancellation
4.93 out of 5 average rating, 72 reviews
4.93 (72)
Flat in Portland
Back Cove Retreat | Walk, Relax, Explore
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
17–22 Oct
17–22 Oct
$2,035 SGD
Show price breakdown
for 5 nights
$2,035 SGD for 5 nights
Free cancellation
New place to stay
New
Flat in Cumberland
Brand new 1 Bedroom. Close to Portland
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
27 Aug – 1 Sept
27 Aug – 1 Sept
$1,740 SGD
$1,408 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Home in Poland
Sunset Cove I
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$3,365 SGD
$2,784 SGD
Show price breakdown
for 5 nights
Free cancellation
4.93 out of 5 average rating, 109 reviews
4.93 (109)
1
2
3
4
…
15