Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
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
Gift cards
Log in or sign up
filters
Filters
Price
Price filter
Type of place
Type of place filter
Show map
Search results; Over 1,000 homes
Over 1,000 homes
Top guest favourite
Guest favourite
Guest house in Cumberland
Cottage Under a Crabapple Tree
Studio
,
·
1 bed
,
·
1 private bathroom
14–19 Oct
14–19 Oct
£971
total
Show price breakdown
£971 total
,
·
4.95 out of 5 average rating, 311 reviews
4.95 (311)
Top guest favourite
Guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
13–18 Sept
13–18 Sept
£2,150
£1,997
total
Show price breakdown
5.0 out of 5 average rating, 23 reviews
5.0 (23)
Top guest favourite
Guest favourite
Home in Bridgton
Lake Front Cabin on Desirable Highland Lake
3 bedrooms
3 bedrooms
,
·
8 beds
8 beds
20–25 Sept
20–25 Sept
£1,025
total
Show price breakdown
£1,025 total
Free cancellation
4.98 out of 5 average rating, 63 reviews
4.98 (63)
Top guest favourite
Guest favourite
Cottage in Harpswell
Updated 1890s Cottage, Private Waterfront, Firepit
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
12–17 Sept
12–17 Sept
£3,672
£2,778
total
Show price breakdown
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Guest favourite
Guest favourite
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
17–22 Sept
17–22 Sept
£2,275
£1,831
total
Show price breakdown
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Top guest favourite
Guest favourite
Cabin in Windham
Updated Cabin Little Sebago Lake
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
8–13 Jul
8–13 Jul
£2,955
total
Show price breakdown
£2,955 total
Free cancellation
5.0 out of 5 average rating, 30 reviews
5.0 (30)
Top guest favourite
Guest favourite
Home in Gray
cozy 3 bedroom ranch with deck and screen porch
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
5–10 Oct
5–10 Oct
£1,366
£1,225
total
Show price breakdown
Free cancellation
4.98 out of 5 average rating, 90 reviews
4.98 (90)
Home in Windham
Beautiful Sebago Lake Getaway!
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
13–18 Sept
13–18 Sept
£2,314
total
Show price breakdown
£2,314 total
New place to stay
New
Top guest favourite
Guest favourite
Home in Windham
Enjoy Sunsets at Welcoming Lake Front Property
2 bedrooms
2 bedrooms
,
·
5 beds
5 beds
26 Sept – 1 Oct
26 Sept – 1 Oct
£1,609
£1,436
total
Show price breakdown
Free cancellation
4.93 out of 5 average rating, 55 reviews
4.93 (55)
Top guest favourite
Guest favourite
Cabin in Freeport
Chickadee A-Frame
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
11–16 Oct
11–16 Oct
£2,446
£1,739
total
Show price breakdown
Free cancellation
4.98 out of 5 average rating, 88 reviews
4.98 (88)
Top guest favourite
Guest favourite
Guest suite in Freeport
Studio Apartment in Freeport
3 beds
3 beds
17–22 Oct
17–22 Oct
£788
total
Show price breakdown
£788 total
4.97 out of 5 average rating, 144 reviews
4.97 (144)
Top guest favourite
Guest favourite
Cottage in Windham
Cozy Maine Lakefront Paradise
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
21–26 Sept
21–26 Sept
£1,803
total
Show price breakdown
£1,803 total
4.96 out of 5 average rating, 23 reviews
4.96 (23)
Top 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
24–29 Oct
24–29 Oct
£722
£632
total
Show price breakdown
Free cancellation
4.94 out of 5 average rating, 555 reviews
4.94 (555)
Top guest favourite
Guest favourite
Home in Oxford
Exclusive Waterfront Cabin | Sauna | Private Beach
3 bedrooms
3 bedrooms
,
·
7 beds
7 beds
20–25 Sept
20–25 Sept
£1,710
£1,493
total
Show price breakdown
5.0 out of 5 average rating, 11 reviews
5.0 (11)
Guest favourite
Guest favourite
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
22–27 Sept
22–27 Sept
£1,967
£1,803
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Top guest favourite
Guest favourite
Cottage in Raymond
Lovely Lakefront Cottage - Book Your Fall GetAway!
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
16–21 Oct
16–21 Oct
£2,046
total
Show price breakdown
£2,046 total
Free cancellation
5.0 out of 5 average rating, 98 reviews
5.0 (98)
Top guest favourite
Guest favourite
Home in Raymond
Spacious Lakehouse +Private Dock+Firepit+Kayaks
2 bedrooms
2 bedrooms
,
·
2 king beds
2 king beds
24–29 Oct
24–29 Oct
£1,377
total
Show price breakdown
£1,377 total
Free cancellation
4.97 out of 5 average rating, 32 reviews
4.97 (32)
Top guest favourite
Guest favourite
Flat in Gray
Two bedroom duplex across st from crystal lake
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
20–25 Sept
20–25 Sept
£765
£610
total
Show price breakdown
4.96 out of 5 average rating, 183 reviews
4.96 (183)
Top guest favourite
Guest favourite
Home in Cumberland
Forest Lake Cottage
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
25–30 Oct
25–30 Oct
£949
£786
total
Show price breakdown
Free cancellation
4.96 out of 5 average rating, 74 reviews
4.96 (74)
1
2
3
4
…
15