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Compare 147 Vacation Homes in Winthrop with updated reviews, rates, and availability.

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Beautiful lakeside 4 bedroom retreat with private dock and walkout basement
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

Whispering Waters Farmhouse/Barn
Whispering Waters Farmhouse/Barn

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
10.0 out of 10, Exceptional, (240)

The Modern Maine Retreat
The Modern Maine Retreat
10.0 out of 10, Exceptional, (3)

Brand New Waterfront Lake House (completed July 2021)
Brand New Waterfront Lake House (completed July 2021)
10.0 out of 10, Exceptional, (22)

Veedon Fleece on the Lake
Veedon Fleece on the Lake
10.0 out of 10, Exceptional, (15)

Great Pond Waterfront: Dog-friendly Home Near Colby College
Great Pond Waterfront: Dog-friendly Home Near Colby College
9.6 out of 10, Exceptional, (30)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Winthrop

Cottage on Cobbosseecontee Lake. Dates available.
Cottage on Cobbosseecontee Lake. Dates available.
10.0 out of 10, Exceptional, (162)

Dog Friendly Cabin Right On The Water!!!
Dog Friendly Cabin Right On The Water!!!
2.0 out of 10, (1)

Escape to our cozy Winthrop cabin on Dexter Pond
Escape to our cozy Winthrop cabin on Dexter Pond
10.0 out of 10, Exceptional, (11)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Winthrop hotels
Recent reviews of Winthrop hotels

Cottage on Cobbosseecontee Lake. Dates available.
5/5 Excellent
Another great stay!!
"Second time at this location, this time to ice fish. Amazing location... cant get any closer to the lake!! All amenities are great, furniture super comfy. To incude the bed and pillows!! Will be back again this summer!! "
A verified traveler stayed at Cottage on Cobbosseecontee Lake. Dates available.
Posted 3 days ago