A wooden signpost with 'WINTHROP' written on it, surrounded by greenery and trees.

Winthrop cottages

We found 35 cottages — enter your dates for availability

Explore Winthrop cottage rentals

Image of Discover your retreat - 3-bedroom cottage in Winthrop

Premier Host

Discover your retreat - 3-bedroom cottage in Winthrop

Sleeps 4 · 3 bedrooms · 1 bathroom

Image of Charming 2BR Lakefront Cottage on Serene Cobbossee w/ Kayaks, A/C

Premier Host

Charming 2BR Lakefront Cottage on Serene Cobbossee w/ Kayaks, A/C

Sleeps 6 · 2 bedrooms · 2 bathrooms

Image of Cozy Keyes Cottage | Lakefront • Dock • Kayaks

Cozy Keyes Cottage | Lakefront • Dock • Kayaks

Sleeps 5 · 2 bedrooms · 1 bathroom

Image of The Little Grey Duck Cottage on Cobbossee Lake

The Little Grey Duck Cottage on Cobbossee Lake

Sleeps 5 · 1 bedroom · 1 bathroom

Image of Life on the Lake with Private Dock & Fire Pit!

Life on the Lake with Private Dock & Fire Pit!

Sleeps 6 · 2 bedrooms · 1 bathroom

Image of Spacious Lakefront Home, Large deck, A/C, Private Dock!

Spacious Lakefront Home, Large deck, A/C, Private Dock!

Sleeps 8 · 3 bedrooms · 1 bathroom

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Enjoy full kitchens, laundry, pools, gardens and more
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