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Winthrop Vacation Rentals

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

Loon Cottage on Cobbosseecontee Lake

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Rustic lakefront home w/ private dock, wood fireplace & modern conveniences, vacation rental in Winthrop

Rustic lakefront home w/ private dock, wood fireplace & modern conveniences

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Custom Waterfront Cottage w/ Loft on Pristine Narrows Pond, vacation rental in Winthrop

Custom Waterfront Cottage w/ Loft on Pristine Narrows Pond

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Lakefront Cabin, Great View, Private Dock, vacation rental in Winthrop

Charming Lakefront Cabin, Great View, Private Dock

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Cottage on Maranacook Lake w/ Updated Dock!, vacation rental in Winthrop

Cozy Cottage on Maranacook Lake w/ Updated Dock!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Enjoy Sunset views on tranquil Dexter Pond, vacation rental in Winthrop

Enjoy Sunset views on tranquil Dexter Pond

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Quintessential Lakefront Cottage with Wonderful Views!, vacation rental in Winthrop

Quintessential Lakefront Cottage with Wonderful Views!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Quintessential Lakefront Cottage with Amazing Views!, vacation rental in Winthrop

Quintessential Lakefront Cottage with Amazing Views!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Teaberry Cottage! Quiet Setting On The Lake, All The Modern Comforts Of Home, vacation rental in Winthrop

Teaberry Cottage! Quiet Setting On The Lake, All The Modern Comforts Of Home

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Classic Maine Cottage Located On A Point, Kayaks, Wifi & Cable, vacation rental in Winthrop

Classic Maine Cottage Located On A Point, Kayaks, Wifi & Cable

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cabin on Long Pond, just steps to lake., vacation rental in Winthrop

Cabin on Long Pond, just steps to lake.

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Great  Vacation Home on 9 Mile Cobbossee Lake in Monmouth, vacation rental in Winthrop

Great Vacation Home on 9 Mile Cobbossee Lake in Monmouth

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Family Cottage On Maranacook Lake  W/ WIFI, vacation rental in Winthrop

Family Cottage On Maranacook Lake W/ WIFI

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Pristine Parker Pond - A Hidden Gem, vacation rental in Winthrop

Pristine Parker Pond - A Hidden Gem

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakeside retreat in Central Maine, vacation rental in Winthrop

Lakeside retreat in Central Maine

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Stress-Eraser, vacation rental in Winthrop

Lakefront Stress-Eraser

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private and Cozy Cottage, Excellent Fishing And Swimming; Sleeps 6., vacation rental in Winthrop

Private and Cozy Cottage, Excellent Fishing And Swimming; Sleeps 6.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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130' Of Waterfront On Lake Cobbosseecontee, vacation rental in Winthrop

130' Of Waterfront On Lake Cobbosseecontee

4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Maine Cabin on the Water, vacation rental in Winthrop

Maine Cabin on the Water

5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful Year-Round West Facing Cottage on Maine Lake with Dock, vacation rental in Winthrop

Beautiful Year-Round West Facing Cottage on Maine Lake with Dock

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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2 bedroom fully furnished camp on Tacoma Lakes, Litchfield, vacation rental in Winthrop

2 bedroom fully furnished camp on Tacoma Lakes, Litchfield

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private Lake Front Retreat, vacation rental in Winthrop

Private Lake Front Retreat

1 bedroom
3 bathrooms
Sleeps 4
Match: Sleeps
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Room near the Maine Statehouse, vacation rental in Winthrop

Room near the Maine Statehouse

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Villa on Cobbossee Lake, private beach, lake view,, vacation rental in Winthrop

Villa on Cobbossee Lake, private beach, lake view,

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Veedon Fleece on the Lake, vacation rental in Winthrop

Veedon Fleece on the Lake

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Family Friendly Cottage on Androscoggin Lake, vacation rental in Winthrop

Family Friendly Cottage on Androscoggin Lake

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Peaceful family friendly lakeside cottage for rent, vacation rental in Winthrop

Peaceful family friendly lakeside cottage for rent

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Reysol- Costa Saracena, vacation rental in Winthrop

Reysol- Costa Saracena

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Appartamento Costa, vacation rental in Winthrop

Appartamento Costa

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Beautiful lake house on Tacoma Lakes near Coast, vacation rental in Winthrop

Beautiful lake house on Tacoma Lakes near Coast

4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Rustic lakefront home w/ private dock, wood fireplace & modern conveniences, vacation rental in Winthrop

Rustic lakefront home w/ private dock, wood fireplace & modern conveniences

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Winthrop Home w/ Elevated Deck & 170-ft Lakefront!, vacation rental in Winthrop

Winthrop Home w/ Elevated Deck & 170-ft Lakefront!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lovely lakefront home w/ private dock, screened porch, firepit & gorgeous view!, vacation rental in Winthrop

Lovely lakefront home w/ private dock, screened porch, firepit & gorgeous view!

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Star Point on Snow Pond in the Belgrade Lakes, vacation rental in Winthrop

Star Point on Snow Pond in the Belgrade Lakes

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Lakefront Winthrop Home w/Outdoor Bar, Deck & Dock, vacation rental in Winthrop

Lakefront Winthrop Home w/Outdoor Bar, Deck & Dock

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Room #1 at the Maple Hill Farm Inn -- Augusta and Hallowell, Maine, vacation rental in Winthrop

Room #1 at the Maple Hill Farm Inn -- Augusta and Hallowell, Maine

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Room #4 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine, vacation rental in Winthrop

Room #4 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Room #6 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine, vacation rental in Winthrop

Room #6 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Room #5 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine, vacation rental in Winthrop

Room #5 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Room #7 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine, vacation rental in Winthrop

Room #7 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Room #3 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine, vacation rental in Winthrop

Room #3 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Room #8 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine, vacation rental in Winthrop

Room #8 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Room #2 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine, vacation rental in Winthrop

Room #2 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Cozy Home w/Vineyard, Working Farm & Fall Foliage, vacation rental in Winthrop

Cozy Home w/Vineyard, Working Farm & Fall Foliage

4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Old School House with river view, vacation rental in Winthrop

Old School House with river view

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Pine Cone Yurt, vacation rental in Winthrop

Pine Cone Yurt

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Cozy Cottage w/ Dock of Annabessacook Lake!, vacation rental in Winthrop

NEW! Cozy Cottage w/ Dock of Annabessacook Lake!

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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NEW! Life on the Lake w/ Private Dock & Fire Pit!, vacation rental in Winthrop

NEW! Life on the Lake w/ Private Dock & Fire Pit!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Well-Suited Suite at Vista of Maine Vineyard!, vacation rental in Winthrop

NEW! Well-Suited Suite at Vista of Maine Vineyard!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Lake Escape w/ Private Dock, Kayaks & Canoe!, vacation rental in Winthrop

NEW! Lake Escape w/ Private Dock, Kayaks & Canoe!

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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