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Winthrop Vacation Rentals

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15 rentals in Winthrop.
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Loon Cottage on Cobbosseecontee Lake, vacation rental in Winthrop
Loon Cottage on Cobbosseecontee Lake, vacation rental in Winthrop
Loon Cottage on Cobbosseecontee Lake, vacation rental in Winthrop

Loon Cottage on Cobbosseecontee Lake

Rental Home
3 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
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Rustic, peaceful cabin on Lake Cobbossee; Perfect for summer or leaf season!, vacation rental in Winthrop
Rustic, peaceful cabin on Lake Cobbossee; Perfect for summer or leaf season!, vacation rental in Winthrop
Rustic, peaceful cabin on Lake Cobbossee; Perfect for summer or leaf season!, vacation rental in Winthrop

Rustic, peaceful cabin on Lake Cobbossee; Perfect for summer or leaf season!

Rental Home
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Walk out beach in private cove on Cobboossee Lake, vacation rental in Winthrop
Walk out beach in private cove on Cobboossee Lake, vacation rental in Winthrop
Walk out beach in private cove on Cobboossee Lake, vacation rental in Winthrop

Walk out beach in private cove on Cobboossee Lake

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Evolve | Peaceful Fisherman's Paradise w/ Fire Pit, vacation rental in Winthrop
Evolve | Peaceful Fisherman's Paradise w/ Fire Pit, vacation rental in Winthrop
Evolve | Peaceful Fisherman's Paradise w/ Fire Pit, vacation rental in Winthrop

Evolve | Peaceful Fisherman's Paradise w/ Fire Pit

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Rustic Lakefront Home with Private Dock, Wood Fireplace, and Modern Conveniences, vacation rental in Winthrop
Rustic Lakefront Home with Private Dock, Wood Fireplace, and Modern Conveniences, vacation rental in Winthrop
Rustic Lakefront Home with Private Dock, Wood Fireplace, and Modern Conveniences, vacation rental in Winthrop

Rustic Lakefront Home with Private Dock, Wood Fireplace, and Modern Conveniences

Rental Home
5 bedrooms
6 bathrooms
Sleeps 9
Match: Sleeps
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Life on the Lake with Private Dock & Fire Pit!, vacation rental in Winthrop
Life on the Lake with Private Dock & Fire Pit!, vacation rental in Winthrop
Life on the Lake with Private Dock & Fire Pit!, vacation rental in Winthrop

Life on the Lake with Private Dock & Fire Pit!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Enjoy Sunset views on tranquil Dexter Pond, vacation rental in Winthrop
Enjoy Sunset views on tranquil Dexter Pond, vacation rental in Winthrop
Enjoy Sunset views on tranquil Dexter Pond, vacation rental in Winthrop

Enjoy Sunset views on tranquil Dexter Pond

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Keyes Cottage, vacation rental in Winthrop
Cozy Keyes Cottage, vacation rental in Winthrop
Cozy Keyes Cottage, vacation rental in Winthrop

Cozy Keyes Cottage

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Family friendly, 2-Bedroom cottage with lakeview, vacation rental in Winthrop
Family friendly, 2-Bedroom cottage with lakeview, vacation rental in Winthrop
Family friendly, 2-Bedroom cottage with lakeview, vacation rental in Winthrop

Family friendly, 2-Bedroom cottage with lakeview

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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WALK TO TOWN BEACH, KAYAK FROM BACKYARD, DOG FRIENDLY & SKIING NEARBY, vacation rental in Winthrop
WALK TO TOWN BEACH, KAYAK FROM BACKYARD, DOG FRIENDLY & SKIING NEARBY, vacation rental in Winthrop
WALK TO TOWN BEACH, KAYAK FROM BACKYARD, DOG FRIENDLY & SKIING NEARBY, vacation rental in Winthrop

WALK TO TOWN BEACH, KAYAK FROM BACKYARD, DOG FRIENDLY & SKIING NEARBY

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Walk to downtown and the town beach or kayak from backyard to Lake Annabessacook, vacation rental in Winthrop
Walk to downtown and the town beach or kayak from backyard to Lake Annabessacook, vacation rental in Winthrop
Walk to downtown and the town beach or kayak from backyard to Lake Annabessacook, vacation rental in Winthrop

Walk to downtown and the town beach or kayak from backyard to Lake Annabessacook

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Little Landing Cottage, vacation rental in Winthrop
Little Landing Cottage, vacation rental in Winthrop
Little Landing Cottage, vacation rental in Winthrop

Little Landing Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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DUCK INN | WAYNE, MAINE | CENTRAL LOCATION |  COUNTRY LIVING ON THE WATER |, vacation rental in Winthrop
DUCK INN | WAYNE, MAINE | CENTRAL LOCATION |  COUNTRY LIVING ON THE WATER |, vacation rental in Winthrop
DUCK INN | WAYNE, MAINE | CENTRAL LOCATION |  COUNTRY LIVING ON THE WATER |, vacation rental in Winthrop

DUCK INN | WAYNE, MAINE | CENTRAL LOCATION | COUNTRY LIVING ON THE WATER |

Rental Home
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Cabin on Cobbossee Lake near Lakeside Marina, vacation rental in Winthrop
Cozy Cabin on Cobbossee Lake near Lakeside Marina, vacation rental in Winthrop
Cozy Cabin on Cobbossee Lake near Lakeside Marina, vacation rental in Winthrop

Cozy Cabin on Cobbossee Lake near Lakeside Marina

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Loon Cove Lake House, vacation rental in Winthrop
Loon Cove Lake House, vacation rental in Winthrop
Loon Cove Lake House, vacation rental in Winthrop

Loon Cove Lake House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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