Winthrop, Maine

Vacation Rentals in Winthrop, Maine

Discover 25 vacation rental properties in Winthrop. From 1 to 6 bedrooms. Average $310/night. 100% have pools.

25 verified listings Book securely on VRBO Prices updated March 2026

25 properties available

Peaceful Fisherman's Paradise w/ Deck + Fire Pit!

Peaceful Fisherman's Paradise w/ Deck + Fire Pit!

2 beds 1 bath
PoolA/CWiFiBalcony
$203/night
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Cottage on Cobbosseecontee Lake. Dates available.

Cottage on Cobbosseecontee Lake. Dates available.

3 beds 1 bath
PoolA/CWiFiBalcony
$220/night
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Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit

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

2 beds 1 bath
PoolA/CWiFiBalcony
$284/night
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Walk to TownBeach or kayak from backyard to Lake Annabessacook. Walk downtown

Walk to TownBeach or kayak from backyard to Lake Annabessacook. Walk downtown

3 beds 1 bath
PoolA/CWiFiBalcony
$222/night
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Pet friendly, Family Homestead 1 hr from the coast!

Pet friendly, Family Homestead 1 hr from the coast!

6 beds 2 baths
PoolA/CWiFiBalcony
$605/night
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Cozy cabin on a peaceful pond. Enjoy the amenities of the Kennebec Valley Area.

Cozy cabin on a peaceful pond. Enjoy the amenities of the Kennebec Valley Area.

2 beds 1 bath
PoolA/CWiFiBalcony
$203/night
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Little Landing Cottage- Cozy Lakefront Oasis

Little Landing Cottage- Cozy Lakefront Oasis

1 bed 1 bath
PoolA/CWiFiBalcony
$441/night
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Rustic, peaceful cabin on Lake Cobbossee; WIFI, ADA friendly, sleeps 10.

Rustic, peaceful cabin on Lake Cobbossee; WIFI, ADA friendly, sleeps 10.

3 beds 2 baths
PoolA/CWiFiBalcony
$251/night
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ANNABESSACOOK WATERFRONT WITH DOCK

ANNABESSACOOK WATERFRONT WITH DOCK

3 beds 1 bath
PoolA/CWiFiBalcony
$319/night
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Perfect getaway on the lake!

Perfect getaway on the lake!

2 beds 1 bath
PoolA/CWiFiBalcony
$352/night
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Lakefront Cottage - sleeps 6 - 2 baths

Lakefront Cottage - sleeps 6 - 2 baths

3 beds 2 baths
PoolA/CWiFiBalcony
$409/night
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Peaceful lakefront home steps from the water. Private dock!

Peaceful lakefront home steps from the water. Private dock!

3 beds 1 bath
PoolA/CWiFiBalcony
$279/night
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Historic Lake Front Home on Cobbosseeconte Lake

Historic Lake Front Home on Cobbosseeconte Lake

5 beds 1 bath
PoolA/CWiFiBalcony
$353/night
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Family friendly, 2-Bedroom cottage with lakeview

Family friendly, 2-Bedroom cottage with lakeview

2 beds 1 bath
PoolA/CWiFiBalcony
$154/night
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Cozy Keyes Cottage- Rare Lakefront Getaway

Cozy Keyes Cottage- Rare Lakefront Getaway

2 beds 1 bath
PoolA/CWiFiBalcony
$442/night
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Private waterfront with stunning views, wrap around deck, and a dock for boating

Private waterfront with stunning views, wrap around deck, and a dock for boating

3 beds 1 bath
PoolA/CWiFiBalcony
$323/night
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Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area

1 bed 1 bath
PoolA/CWiFiBalcony
$150/night
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Spectacular Cottage on COBBOSSEE LAKE!

Spectacular Cottage on COBBOSSEE LAKE!

3 beds 1 bath
PoolA/CWiFiBalcony
$301/night
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Life on the Lake with Private Dock & Fire Pit!

Life on the Lake with Private Dock & Fire Pit!

2 beds 1 bath
PoolA/CWiFiBalcony
$251/night
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Cozy Cabin on Cobbossee Lake near Lakeside Marina

Cozy Cabin on Cobbossee Lake near Lakeside Marina

2 beds 1 bath
PoolA/CWiFiBalcony
$203/night
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Enjoy Sunset views on tranquil Dexter Pond

Enjoy Sunset views on tranquil Dexter Pond

2 beds 1 bath
PoolA/CWiFiBalcony
$246/night
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Maine Vacation House Cobbosseecontee Lake

Maine Vacation House Cobbosseecontee Lake

3 beds 3 baths
PoolA/CWiFiBalcony
$508/night
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Lakefront, dog-friendly home with 3 docks & 2 boats - sleeps extra in summer

Lakefront, dog-friendly home with 3 docks & 2 boats - sleeps extra in summer

4 beds 2 baths
PoolA/CWiFiBalcony
$400/night
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Lakefront Cottage on beautiful Lake Maranacook in Winthrop, ME.

Lakefront Cottage on beautiful Lake Maranacook in Winthrop, ME.

3 beds 2 baths
PoolA/CWiFiBalcony
$401/night
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Dog Friendly Cabin Right On The Water!!!

Dog Friendly Cabin Right On The Water!!!

2 beds 1 bath
PoolA/CWiFiBalcony
$241/night
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