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 Windham
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 Windham
Over 1,000 homes in Windham
Top guest favourite
Guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom
,
·
1 bed
,
·
1 shared bathroom
13–18 Oct
13–18 Oct
$1,208 SGD
Show price breakdown
for 5 nights
$1,208 SGD for 5 nights
,
·
4.99 out of 5 average rating, 297 reviews
4.99 (297)
Top guest favourite
Guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
17–22 Oct
17–22 Oct
$1,769 SGD
$1,461 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.95 out of 5 average rating, 195 reviews
4.95 (195)
Guest favourite
Guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
24–29 Aug
24–29 Aug
$2,089 SGD
Show price breakdown
for 5 nights
$2,089 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Top guest favourite
Guest favourite
Home in Windham
Private Pool and Hot Tub! Mins to Sebago Lake.
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
11–16 Oct
11–16 Oct
$5,491 SGD
Show price breakdown
for 5 nights
$5,491 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 29 reviews
5.0 (29)
Top guest favourite
Guest favourite
Home in Windham
Maine Vacation Home on the Water
4 bedrooms
4 bedrooms
,
·
9 beds
9 beds
12–17 Sept
12–17 Sept
$5,931 SGD
Show price breakdown
for 5 nights
$5,931 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 61 reviews
5.0 (61)
Guest favourite
Guest favourite
Home in Windham
Enjoy Sunsets at Welcoming Lake Front Property
2 bedrooms
2 bedrooms
,
·
5 beds
5 beds
9–14 Sept
9–14 Sept
$2,355 SGD
Show price breakdown
for 5 nights
$2,355 SGD for 5 nights
Pay $0 today
Free cancellation
4.92 out of 5 average rating, 49 reviews
4.92 (49)
Top guest favourite
Guest favourite
Cottage in Windham
The Purple House by Pettingill Pond
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
25–30 Sept
25–30 Sept
$1,689 SGD
Show price breakdown
for 5 nights
$1,689 SGD for 5 nights
Free cancellation
4.9 out of 5 average rating, 97 reviews
4.9 (97)
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
29 Aug – 3 Sept
29 Aug – 3 Sept
$3,702 SGD
$3,270 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Home in Windham
Cozy Camp on the lake
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
5–10 Oct
5–10 Oct
$2,073 SGD
Show price breakdown
for 5 nights
$2,073 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 53 reviews
5.0 (53)
Superhost
Superhost
Home in Falmouth
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
5–10 Sept
5–10 Sept
$3,898 SGD
$3,135 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favourite
Guest favourite
Home in Windham
Windham Lake Retreat | Knotty Pine Cabin Fire pit
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
5–10 Oct
5–10 Oct
$1,785 SGD
Show price breakdown
for 5 nights
$1,785 SGD for 5 nights
Pay $0 today
Free cancellation
4.94 out of 5 average rating, 62 reviews
4.94 (62)
Top guest favourite
Guest favourite
Flat in Windham
Maple Brook
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
14–19 Oct
14–19 Oct
$1,592 SGD
Show price breakdown
for 5 nights
$1,592 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 20 reviews
5.0 (20)
Top guest favourite
Guest favourite
Flat in Windham
1 Bedroom with Beach Access
1 bedroom
1 bedroom
,
·
2 beds
2 beds
20–25 Sept
20–25 Sept
$1,398 SGD
Show price breakdown
for 5 nights
$1,398 SGD for 5 nights
Pay $0 today
Free cancellation
4.97 out of 5 average rating, 61 reviews
4.97 (61)
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
$5,166 SGD
Show price breakdown
for 5 nights
$5,166 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 29 reviews
5.0 (29)
Top guest favourite
Guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
9–14 Oct
9–14 Oct
$5,033 SGD
Show price breakdown
for 5 nights
$5,033 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Top guest favourite
Guest favourite
Guest suite in Windham
Millers Private Studio on Highland Lake
2 beds
2 beds
17–22 Sept
17–22 Sept
$887 SGD
Show price breakdown
for 5 nights
$887 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 215 reviews
4.93 (215)
Top guest favourite
Guest favourite
Flat in Windham
Christmas Tree Farm apartment
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
7–12 Sept
7–12 Sept
$1,360 SGD
Show price breakdown
for 5 nights
$1,360 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 16 reviews
5.0 (16)
Top guest favourite
Guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
1 bedroom
1 bedroom
,
·
2 beds
2 beds
2–7 Sept
2–7 Sept
$2,042 SGD
Show price breakdown
for 5 nights
$2,042 SGD for 5 nights
Pay $0 today
Free cancellation
4.96 out of 5 average rating, 235 reviews
4.96 (235)
Top guest favourite
Guest favourite
Flat in Windham
The Nest
1 bedroom
1 bedroom
,
·
2 beds
2 beds
23–28 Aug
23–28 Aug
$3,069 SGD
Show price breakdown
for 5 nights
$3,069 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 21 reviews
5.0 (21)
1
2
3
4
…
15