Search results; Over 1,000 places in Windham

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Guest favorite
Guest suite in Windham
Millers Private Studio on Highland Lake
4 guestsStudio2 beds1 bath
May 27 – Jun 1
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May 27 – Jun 1
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ﺩ.ﺇ2,583 for 5 nights
for 5 nights

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Top guest favorite
Guesthouse in Windham
Cottage on Black Brook Preserve
Free cancellation
Jul 26 – 31
ﺩ.ﺇ2,906 for 5 nights
for 5 nights
4.99 out of 5 average rating, 256 reviews
Top guest favorite
Home in Windham
Modern Chic Home in Windham
3 beds
May 18 – 23
ﺩ.ﺇ5,166 for 5 nights
for 5 nights
5.0 out of 5 average rating, 44 reviews
Guest favorite
Cottage in Windham
Cozy camp near highland lake
2 queen beds
May 27 – Jun 1
ﺩ.ﺇ3,039 for 5 nights
for 5 nights
4.82 out of 5 average rating, 139 reviews
Apartment in Windham
1 Bedroom with Beach Access
2 beds
May 18 – 23
ﺩ.ﺇ3,228 for 5 nights
for 5 nights
New place to stay
Guest favorite
Tiny home in Windham
The Chickadee House on Pettingill Pond
Free cancellation
Aug 28 – Sep 2
ﺩ.ﺇ3,889 for 5 nights
for 5 nights
4.96 out of 5 average rating, 204 reviews
Guest favorite
Guest suite in Gorham
Farmhouse stay, near lakes and St. Joe's College
2 beds
May 16 – 21
ﺩ.ﺇ3,767 for 5 nights
for 5 nights
4.97 out of 5 average rating, 128 reviews
Top guest favorite
Home in Windham
Waterfront Gem walkable to Restaurants!
Free cancellation
Sep 21 – 26
ﺩ.ﺇ4,778 for 5 nights
for 5 nights
4.94 out of 5 average rating, 131 reviews
Top guest favorite
Home in Windham
Maine Vacation Home on the Water
9 beds
May 18 – 23
ﺩ.ﺇ10,375 for 5 nights
for 5 nights
5.0 out of 5 average rating, 28 reviews
Home in Gray
The Lazy Hummingbird
4 beds
May 21 – 26
ﺩ.ﺇ7,542 for 5 nights
for 5 nights
New place to stay
Guest favorite
Hotel in Portland
Portland’s only hotel with unobstructed bay views
1 double bed
May 16 – 21
ﺩ.ﺇ4,016 for 5 nights
for 5 nights
4.96 out of 5 average rating, 47 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
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
Superhost
Home in Windham
Windham Wind Down-Lakefront, Dock, Kayaks, & SUPs
Free cancellation
Jul 29 – Aug 3
ﺩ.ﺇ13,655 for 5 nights
for 5 nights
New place to stay
Guest favorite
Apartment in Falmouth
Peaceful & Cozy Falmouth Getaway
5 beds
May 17 – 22
ﺩ.ﺇ2,562 for 5 nights
for 5 nights
4.9 out of 5 average rating, 86 reviews
Guest favorite
Room in Falmouth
Stay with SydMusician,
Swedish Room in Foreside Farmhouse
Jun 8 – 13
ﺩ.ﺇ2,928 for 5 nights
for 5 nights
4.91 out of 5 average rating, 88 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
Loft in Portland
Large Loft—Walk to Breweries— Coffee Bar—King Bed
Free cancellation
May 24 – 29
ﺩ.ﺇ5,364 for 5 nights
for 5 nights
4.92 out of 5 average rating, 284 reviews
Top guest favorite
Room in Falmouth
Stay with SydMusician,
Green Room at Foreside Farmhouse
May 17 – 22
ﺩ.ﺇ1,915 for 5 nights
for 5 nights
4.99 out of 5 average rating, 70 reviews