Search results; Over 1,000 places in Windham

Prices include all fees

Explore more homes

Top guest favorite
Guesthouse in Windham
Cottage on Black Brook Preserve
Free cancellation
Aug 19 – 24
R14,275 ZAR for 5 nights
for 5 nights
4.99 out of 5 average rating, 257 reviews
Top guest favorite
Apartment in Windham
The Roost - lovely one bedroom efficiency unit
1 bed
Jun 1 – 6
R11,632 ZAR for 5 nights
for 5 nights
4.99 out of 5 average rating, 136 reviews
Top guest favorite
Home in Windham
Modern Chic Home in Windham
3 beds
Jun 9 – 14
R23,157 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 44 reviews
Guest favorite
Guest suite in Windham
Millers Private Studio on Highland Lake
Free cancellation
Sep 2 – 7
R12,689 ZAR for 5 nights
for 5 nights
4.92 out of 5 average rating, 183 reviews
Guest favorite
Cottage in Windham
Cozy camp near highland lake
2 queen beds
Jul 15 – 20
R24,870 ZAR for 5 nights
for 5 nights
4.82 out of 5 average rating, 139 reviews
Superhost
Home in Windham
Windham Wind Down-Lakefront, Dock, Kayaks, & SUPs
Free cancellation
Aug 28 – Sep 2
R66,280 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 4 reviews
Top guest favorite
Home in Windham
Cozy Camp on the lake
Free cancellation
Sep 3 – 8
R30,580 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 35 reviews
Top guest favorite
Home in Windham
Maine Vacation Home on the Water
Free cancellation
Jun 8 – 13
R68,944 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 29 reviews
Guest favorite
Home in Windham
Woodland with Fireplace Home
5 beds
Jun 1 – 6
R43,354 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 12 reviews
Guest favorite
Cottage in Windham
Cozy Cottage on Highland Lake
Free cancellation
Sep 7 – 12
R21,149 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 106 reviews
Guest favorite
Guest suite in Gorham
Farmhouse stay, near lakes and St. Joe's College
2 beds
Jun 3 – 8
R19,308 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 129 reviews
Guest favorite
Home in Windham
The Lake House
4 beds
Jun 24 – 29
R31,723 ZAR for 5 nights
for 5 nights
4.9 out of 5 average rating, 42 reviews
Apartment in Windham
Maple Brook
Free cancellation
Aug 11 – 16
R22,205 ZAR for 5 nights
for 5 nights
Home in Gray
Little Sebago lakefront retreat
10 beds
Jun 13 – 20
R41,240 ZAR for 7 nights
for 7 nights
4.85 out of 5 average rating, 13 reviews
Apartment in Windham
Mill Pond Place
3 beds
Jun 23 – 28
R17,130 ZAR for 5 nights
for 5 nights
4.77 out of 5 average rating, 57 reviews
Home in Gray
The Lazy Hummingbird - Little Sebago home w/ Sauna
4 beds
Jun 10 – 15
R37,052 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Guest favorite
Cabin in Windham
Cozy Private Lake Getaway (Seasonal)
1 bed
Jun 1 – 6
R18,125 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 29 reviews
Home in Windham
Swan's End House: 2300 sf, Sleeps 8, Built in 2018
6 beds
Jun 1 – 6
R51,285 ZAR for 5 nights
for 5 nights