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
Rustic charm close to Portland
2 bedrooms
,
·
3 beds
,
·
2 shared bathrooms
26–31 Jul
26–31 Jul
$1,797 SGD
Show price breakdown
for 5 nights
$1,797 SGD for 5 nights
,
·
4.95 out of 5 average rating, 333 reviews
4.95 (333)
Top guest favourite
Guest favourite
Home in Gray
cozy 3 bedroom ranch with deck and screen porch
4.98 out of 5 average rating, 84 reviews
4.98 (84)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
15–20 Aug
15–20 Aug
$2,027 SGD
Show price breakdown
for 5 nights
$2,027 SGD for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Home in Poland
Hillside Hideaway at Blackcat Mountain
5.0 out of 5 average rating, 5 reviews
5.0 (5)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
9–14 Jul
9–14 Jul
$1,195 SGD
Show price breakdown
for 5 nights
$1,195 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Home in Portland
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
4.96 out of 5 average rating, 168 reviews
4.96 (168)
,
·
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
1.5 bathrooms
1.5 bathrooms
14–19 Sept
14–19 Sept
$4,340 SGD
$3,931 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Cottage in Windham
Cozy camp near highland lake
4.84 out of 5 average rating, 164 reviews
4.84 (164)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,210 SGD
Show price breakdown
for 5 nights
$1,210 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
5.0 out of 5 average rating, 13 reviews
5.0 (13)
,
·
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
4–9 Sept
4–9 Sept
$5,261 SGD
Show price breakdown
for 5 nights
$5,261 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Guest suite in Freeport
Studio Apartment in Freeport
4.98 out of 5 average rating, 124 reviews
4.98 (124)
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
10–15 Aug
10–15 Aug
$1,674 SGD
Show price breakdown
for 5 nights
$1,674 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Naples
Trickey Moose Family Retreat | Fire Pit Kayaks
4.94 out of 5 average rating, 67 reviews
4.94 (67)
,
·
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$3,243 SGD
Show price breakdown
for 5 nights
$3,243 SGD for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Flat in Brunswick
New Modern Townhouse by Bowdoin College & DT(#1)
5.0 out of 5 average rating, 10 reviews
5.0 (10)
,
·
2 bedrooms
2 bedrooms
,
·
2.5 bathrooms
2.5 bathrooms
16–21 Aug
16–21 Aug
$1,488 SGD
Show price breakdown
for 5 nights
$1,488 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
4.95 out of 5 average rating, 192 reviews
4.95 (192)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
26 Sept – 1 Oct
26 Sept – 1 Oct
$2,010 SGD
Show price breakdown
for 5 nights
$2,010 SGD for 5 nights
Pay $0 today
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
9–14 Jul
9–14 Jul
$3,321 SGD
Show price breakdown
for 5 nights
$3,321 SGD for 5 nights
Free cancellation
Home in Old Orchard Beach
3BR 2BA Home w/Pool, Dog Ok, 5 Min Drive to Beach
New place to stay
New
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
3–8 Aug
3–8 Aug
$4,991 SGD
Show price breakdown
for 5 nights
$4,991 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Flat in Portland
The Yankee Dugout
4.98 out of 5 average rating, 186 reviews
4.98 (186)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
31 Aug – 5 Sept
31 Aug – 5 Sept
$1,983 SGD
Show price breakdown
for 5 nights
$1,983 SGD for 5 nights
Pay $0 today
Free cancellation
Flat in South Portland
2 bedroom, 1 bath of coastal comfort & airy charm
New place to stay
New
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
16–21 Aug
16–21 Aug
$1,601 SGD
Show price breakdown
for 5 nights
$1,601 SGD for 5 nights
Pay $0 today
Free cancellation
Superhost
Superhost
Bed and breakfast in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
5.0 out of 5 average rating, 4 reviews
5.0 (4)
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
14–19 Jul
14–19 Jul
$1,333 SGD
Show price breakdown
for 5 nights
$1,333 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Home in Raymond
Lake front home on Little Sebago
5.0 out of 5 average rating, 13 reviews
5.0 (13)
,
·
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
1.5 bathrooms
1.5 bathrooms
7–12 Sept
7–12 Sept
$4,404 SGD
Show price breakdown
for 5 nights
$4,404 SGD for 5 nights
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
18–23 Jul
18–23 Jul
$3,509 SGD
Show price breakdown
for 5 nights
$3,509 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Home in Casco
All seasons Thompson Lake house
5.0 out of 5 average rating, 11 reviews
5.0 (11)
,
·
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,868 SGD
Show price breakdown
for 5 nights
$1,868 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Cottage in Windham
The Purple House by Pettingill Pond
4.9 out of 5 average rating, 96 reviews
4.9 (96)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
25–30 Aug
25–30 Aug
$1,695 SGD
Show price breakdown
for 5 nights
$1,695 SGD for 5 nights
Free cancellation
1
2
3
4
…
15