A white church with a steeple and red accents, surrounded by autumn trees.

Windham cottage rentals

We found 225 cottage rentals — enter your dates for availability

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Image of Lakefront Cottage with New HOT TUB. . Located only 20 minutes from Portland

Lakefront Cottage with New HOT TUB. . Located only 20 minutes from Portland

Sleeps 6 · 2 bedrooms · 1 bathroom

Image of WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND

Premier Host

WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND

Sleeps 5 · 2 bedrooms · 1 bathroom

Image of Rosebud on Little Sebago Lake

Rosebud on Little Sebago Lake

Sleeps 12 · 5 bedrooms · 4 bathrooms

Image of Little Sebago Lake - Private Sandbar With A White Sand Beach - Full Sun

Little Sebago Lake - Private Sandbar With A White Sand Beach - Full Sun

Sleeps 8 · 4 bedrooms · 1 bathroom

Image of Cozy Year-round House right outside Portland Maine on Highland Lake.

Premier Host

Cozy Year-round House right outside Portland Maine on Highland Lake.

Sleeps 7 · 3 bedrooms · 1+ bathroom

Image of The Purple House by Pettingill Pond

The Purple House by Pettingill Pond

Sleeps 6 · 3 bedrooms · 1 bathroom

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