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

Whispering Waters Farmhouse/Barn
Whispering Waters Farmhouse/Barn

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

Private and Calming Waterfront to the Rescue!
Private and Calming Waterfront to the Rescue!
9.6 out of 10, Exceptional, (77)

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

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)

Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
10.0 out of 10, Exceptional, (26)
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

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)

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

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
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

Maine Evergreen Hotel, Ascend Hotel Collection
5/5 Excellent
"Very professional and friendly staff"
A verified traveler stayed at Maine Evergreen Hotel, Ascend Hotel Collection
Posted 1 day ago