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

Winthrop house rentals

We found 154 house rentals — enter your dates for availability

Explore Winthrop house rentals

Image of Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit

Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit

Sleeps 8 · 2 bedrooms · 1 bathroom

Image of Rustic, peaceful lake house on Lake Cobbosseecontee; free WIFI, ADA friendly.

Rustic, peaceful lake house on Lake Cobbosseecontee; free WIFI, ADA friendly.

Sleeps 10 · 3 bedrooms · 2+ bathrooms

Image of Escape to our cozy Winthrop cabin on Dexter Pond

Premier Host

Escape to our cozy Winthrop cabin on Dexter Pond

Sleeps 5 · 2 bedrooms · 0+ bathrooms

Image of Enjoy Sunset views on tranquil Dexter Pond

Enjoy Sunset views on tranquil Dexter Pond

Sleeps 4 · 2 bedrooms · 1 bathroom

Image of Private, sandy beach on Lake Cobbosseecontee!

Premier Host

Private, sandy beach on Lake Cobbosseecontee!

Sleeps 6 · 3 bedrooms · 1 bathroom

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

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Enjoy full kitchens, laundry, pools, gardens and more
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