Search results; Over 1,000 places in Windham

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Top guest favorite
Guesthouse in Windham
Cottage on Black Brook Preserve
Free cancellation
Aug 10 – 15
ﺩ.ﺇ2,906 for 5 nights
for 5 nights
4.99 out of 5 average rating, 256 reviews
Guest favorite
Cottage in Windham
Cozy camp near highland lake
2 queen beds
May 27 – Jun 1
ﺩ.ﺇ3,190 for 5 nights
for 5 nights
4.82 out of 5 average rating, 139 reviews
Guest favorite
Guest suite in Windham
Millers Private Studio on Highland Lake
Free cancellation
Sep 2 – 7
ﺩ.ﺇ2,583 for 5 nights
for 5 nights
4.92 out of 5 average rating, 182 reviews
Top guest favorite
Home in Windham
Modern Chic Home in Windham
3 beds
Jun 2 – 7
ﺩ.ﺇ4,714 for 5 nights
for 5 nights
5.0 out of 5 average rating, 44 reviews
Top guest favorite
Apartment in Westbrook
King bed apartment near Portland with free parking
Free cancellation
May 31 – Jun 5
ﺩ.ﺇ2,136 for 5 nights
for 5 nights
4.95 out of 5 average rating, 64 reviews
Guest favorite
Home in Windham
The Lake House
4 beds
May 24 – 29
ﺩ.ﺇ6,027 for 5 nights
for 5 nights
4.9 out of 5 average rating, 42 reviews
Guest favorite
Cabin in Windham
Cozy Private Lake Getaway (Seasonal)
1 bed
May 26 – 31
ﺩ.ﺇ3,660 for 5 nights
for 5 nights
4.93 out of 5 average rating, 28 reviews
Superhost
Home in Windham
Windham Wind Down-Lakefront, Dock, Kayaks, & SUPs
Free cancellation
Aug 24 – 29
ﺩ.ﺇ11,817 for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Apartment in Windham
Maple Brook
Free cancellation
Aug 11 – 16
ﺩ.ﺇ4,520 for 5 nights
for 5 nights
Top guest favorite
Treehouse in Pownal
The Copper Fox Treehouse
Free cancellation
Jul 19 – 24
ﺩ.ﺇ10,224 for 5 nights
for 5 nights
4.98 out of 5 average rating, 98 reviews
Superhost
Cabin in Raymond
Rustic, cozy cabin on Sebago Lake. A hidden gem.
Free cancellation
Jun 1 – 6
ﺩ.ﺇ3,660 for 5 nights
for 5 nights
4.93 out of 5 average rating, 154 reviews
Guest favorite
Room in Portland
Stay with AnnaHosting for 4 years,
Grey room with private bathroom.
May 24 – 29
ﺩ.ﺇ2,002 for 5 nights
for 5 nights
4.95 out of 5 average rating, 21 reviews
Top guest favorite
Cottage in Windham
Romantic waterfront cottage for two in Maine
Free cancellation
Sep 2 – 7
ﺩ.ﺇ5,963 for 5 nights
for 5 nights
5.0 out of 5 average rating, 77 reviews
Home in Gray
Coveside on Little Sebago
Free cancellation
May 26 – 31
ﺩ.ﺇ8,180 for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Superhost
Farm stay in Westbrook
Summer House at Conant Homestead
Free cancellation
Jun 1 – 6
ﺩ.ﺇ2,217 for 5 nights
for 5 nights
4.76 out of 5 average rating, 169 reviews
Barn in Yarmouth
Maine Barn Studio
1 queen bed
May 19 – 24
ﺩ.ﺇ3,766 for 5 nights
for 5 nights
New place to stay
Guest favorite
Tiny home in Portland
The Garden Cabin Tiny Home
Free cancellation
Jun 15 – 20
ﺩ.ﺇ3,039 for 5 nights
for 5 nights
4.96 out of 5 average rating, 472 reviews
Cabin in Madison
The Waffle Cone Couple's Retreat
Free cancellation
Aug 10 – 15
ﺩ.ﺇ3,681 for 5 nights
for 5 nights
5.0 out of 5 average rating, 4 reviews