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Holiday Homes in Winthrop

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49 rentals in Winthrop.
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Loon Cottage on Cobbosseecontee Lake, holiday 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, holiday 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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Charming Lakefront Cabin, Great View, Private Dock, holiday rental in Winthrop

Charming Lakefront Cabin, Great View, Private Dock

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Walk to downtown and the town beach or kayak from backyard to Lake Annabessacook, holiday rental in Winthrop

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

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Quintessential Lakefront Cottage with Wonderful Views!, holiday rental in Winthrop

Quintessential Lakefront Cottage with Wonderful Views!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Teaberry Cottage! Quiet Setting On The Lake, All The Modern Comforts Of Home, holiday 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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Quintessential Lakefront Cottage with Amazing Views!, holiday rental in Winthrop

Quintessential Lakefront Cottage with Amazing Views!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Cottage In Wildewood Estates, holiday rental in Winthrop

Beautiful Cottage In Wildewood Estates

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Cabin on Long Pond, just steps to lake., holiday rental in Winthrop

Cabin on Long Pond, just steps to lake.

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Luxury Family Home / Retreat Center on Great Pond, holiday rental in Winthrop

Luxury Family Home / Retreat Center on Great Pond

7 bedrooms
9 bathrooms
Sleeps 16
Match: Sleeps
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Great  Vacation Home on 9 Mile Cobbossee Lake in Monmouth, holiday 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, holiday rental in Winthrop

Family Cottage On Maranacook Lake W/ WIFI

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lakeside retreat in Central Maine, holiday rental in Winthrop

Lakeside retreat in Central Maine

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Pristine Parker Pond - A Hidden Gem, holiday rental in Winthrop

Pristine Parker Pond - A Hidden Gem

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Stress-Eraser, holiday 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., holiday 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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Lake Front Chalet on Great Pond, holiday rental in Winthrop

Lake Front Chalet on Great Pond

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

Maine Cabin on the Water

5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Belgrade Lakes vacation home, holiday rental in Winthrop

Belgrade Lakes vacation home

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

Veedon Fleece on the Lake

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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130' Of Waterfront On Lake Cobbosseecontee, holiday rental in Winthrop

130' Of Waterfront On Lake Cobbosseecontee

4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Year-Round West Facing Cottage on Maine Lake with Dock, holiday 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, holiday 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, holiday rental in Winthrop

Private Lake Front Retreat

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

Room near the Maine Statehouse

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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BELGRADE LAKES  MAINE ** GREAT POND **  2 BEDROOM COTTAGE 15 FEET FROM WATER, holiday rental in Winthrop

BELGRADE LAKES MAINE ** GREAT POND ** 2 BEDROOM COTTAGE 15 FEET FROM WATER

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Family Friendly Cottage on Androscoggin Lake, holiday 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, holiday rental in Winthrop

Peaceful family friendly lakeside cottage for rent

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Appartamento Costa, holiday 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, holiday rental in Winthrop

Beautiful lake house on Tacoma Lakes near Coast

4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Peaceful Fisherman's Paradise w/ Deck + Fire Pit!, holiday rental in Winthrop

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Star Point on Snow Pond in the Belgrade Lakes, holiday rental in Winthrop

Star Point on Snow Pond in the Belgrade Lakes

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Room #1 at the Maple Hill Farm Inn -- Augusta and Hallowell, Maine, holiday 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, holiday 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, holiday 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, holiday 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, holiday 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, holiday 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, holiday 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, holiday 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, holiday rental in Winthrop

Cozy Home w/Vineyard, Working Farm & Fall Foliage

4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Lakefront Hartford Cabin w/ Canoe & Boat Ramp, holiday rental in Winthrop

Lakefront Hartford Cabin w/ Canoe & Boat Ramp

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Slippery Rock Trails, LLC, holiday rental in Winthrop

Tentrr Signature Site - Slippery Rock Trails, LLC

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Pine Cone Yurt, holiday 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!, holiday 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!, holiday 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!, holiday 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!, holiday rental in Winthrop

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

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Old School House with river view, holiday rental in Winthrop

Old School House with river view

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Clean, new Eco-friendly Camp: Hidden Treasure on Golden Pond, holiday rental in Winthrop

Clean, new Eco-friendly Camp: Hidden Treasure on Golden Pond

3 bedrooms
2 bathrooms
Sleeps 1
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