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Wellesley Island Holiday Rentals

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50 rentals in Wellesley Island.
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Charming New Home Within Minutes Of Many Activities, holiday rental in Wellesley Island

Charming New Home Within Minutes Of Many Activities

3 bedrooms
2 bathrooms
Sleeps 7
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Waterfront house on Wellesley Island, holiday rental in Wellesley Island

Waterfront house on Wellesley Island

3 bedrooms
2 bathrooms
Sleeps 6
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Thousand Islands New York, holiday rental in Wellesley Island

Thousand Islands New York

2 bedrooms
1 bathroom
Sleeps 4
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Magnificent 6 Bedroom Cottage On The Water With Spectacular Water Views, holiday rental in Wellesley Island

Magnificent 6 Bedroom Cottage On The Water With Spectacular Water Views

6 bedrooms
4 bathrooms
Sleeps 16
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19th Green Luxury Rental on Wellesley Island, holiday rental in Wellesley Island

19th Green Luxury Rental on Wellesley Island

3 bedrooms
2 bathrooms
Sleeps 8
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Picturesque 6 Bedroom Cottage on the Water with Stunning Views of Boldt Castle, holiday rental in Wellesley Island

Picturesque 6 Bedroom Cottage on the Water with Stunning Views of Boldt Castle

6 bedrooms
4 bathrooms
Sleeps 12
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850ft water, 3 acres, Wellesley Island, holiday rental in Wellesley Island

850ft water, 3 acres, Wellesley Island

2 bedrooms
1 bathroom
Sleeps 8
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The Holiday House: In the Middle of it All!, holiday rental in Wellesley Island

The Holiday House: In the Middle of it All!

4 bedrooms
3 bathrooms
Sleeps 8
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Rustic cabin with amazing views on Lake of the Isles, holiday rental in Wellesley Island

Rustic cabin with amazing views on Lake of the Isles

2 bedrooms
1 bathroom
Sleeps 6
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View of Boldt Castle!, holiday rental in Wellesley Island

View of Boldt Castle!

1 bedroom
1 bathroom
Sleeps 4
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Beautiful New Loon Cottage on The River at The Ledges Resort and Marina, holiday rental in Wellesley Island

Beautiful New Loon Cottage on The River at The Ledges Resort and Marina

2 bedrooms
1 bathroom
Sleeps 4
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3 Bdrm, 2 Bath Luxury Waterfront Villa With Boathouse Fishing & Boating Paradise, holiday rental in Wellesley Island

3 Bdrm, 2 Bath Luxury Waterfront Villa With Boathouse Fishing & Boating Paradise

3 bedrooms
2 bathrooms
Sleeps 7
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Millionaires Row with Close-up Views of the Ships and Castle, holiday rental in Wellesley Island

Millionaires Row with Close-up Views of the Ships and Castle

3 bedrooms
2 bathrooms
Sleeps 8
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Thousand Island Gem - Harbor Villa Condo, holiday rental in Wellesley Island

Thousand Island Gem - Harbor Villa Condo

2 bedrooms
2 bathrooms
Sleeps 10
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1000 Islands Region-The river, The views, The only thing missing is YOU!, holiday rental in Wellesley Island

1000 Islands Region-The river, The views, The only thing missing is YOU!

2 bedrooms
2 bathrooms
Sleeps 5
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Charming Winery Home, holiday rental in Wellesley Island

Charming Winery Home

3 bedrooms
2 bathrooms
Sleeps 7
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Relax Outdoors In This Updated Village Home... Walking Distance to Downtown, holiday rental in Wellesley Island

Relax Outdoors In This Updated Village Home... Walking Distance to Downtown

2 bedrooms
2 bathrooms
Sleeps 4
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Cottage rental in the Thousand Islands, Alexandria Bay, NY with dock, holiday rental in Wellesley Island

Cottage rental in the Thousand Islands, Alexandria Bay, NY with dock

3 bedrooms
2 bathrooms
Sleeps 8
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Village Waterfront Home!! Walking Distance To All Attractions!, holiday rental in Wellesley Island

Village Waterfront Home!! Walking Distance To All Attractions!

5 bedrooms
2 bathrooms
Sleeps 10
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It's a floating cottage!, holiday rental in Wellesley Island

It's a floating cottage!

3 bedrooms
2 bathrooms
Sleeps 8
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Vista Point On The Main Channel, holiday rental in Wellesley Island

Vista Point On The Main Channel

4 bedrooms
3 bathrooms
Sleeps 10
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Lighthouse Cottage - This cottage is floating in the Heart of the 1000 Islands, holiday rental in Wellesley Island

Lighthouse Cottage - This cottage is floating in the Heart of the 1000 Islands

3 bedrooms
2 bathrooms
Sleeps 8
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The Ledges Resort & Marina, holiday rental in Wellesley Island

The Ledges Resort & Marina

2 bedrooms
1 bathroom
Sleeps 4
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Waterfront Luxury Boathouse Villa in 1000 Islands - Alexandria Bay, holiday rental in Wellesley Island

Waterfront Luxury Boathouse Villa in 1000 Islands - Alexandria Bay

2 bedrooms
2 bathrooms
Sleeps 6
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The Ledges Resort & Marina, holiday rental in Wellesley Island

The Ledges Resort & Marina

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Making Memories on the River, holiday rental in Wellesley Island

Making Memories on the River

4 bedrooms
2 bathrooms
Sleeps 10
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Watermark Luxe Waterfront Cottages  del Sol, holiday rental in Wellesley Island

Watermark Luxe Waterfront Cottages del Sol

2 bedrooms
1 bathroom
Sleeps 4
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Watermark Luxe Waterfront Cottages Riveria, holiday rental in Wellesley Island

Watermark Luxe Waterfront Cottages Riveria

4 bedrooms
3 bathrooms
Sleeps 8
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New cottage at The Ledges Resort & Marina on The St. Lawrence River!, holiday rental in Wellesley Island

New cottage at The Ledges Resort & Marina on The St. Lawrence River!

2 bedrooms
2 bathrooms
Sleeps 8
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Private Island, 1000 Islands, Gananoque / Ivy Lea, holiday rental in Wellesley Island

Private Island, 1000 Islands, Gananoque / Ivy Lea

3 bedrooms
1 bathroom
Sleeps 6
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Stunning Boathouse Condo, holiday rental in Wellesley Island

Stunning Boathouse Condo

3 bedrooms
2 bathrooms
Sleeps 6
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Watermark Luxe Waterfront Cottages Bella Vista, holiday rental in Wellesley Island

Watermark Luxe Waterfront Cottages Bella Vista

1 bedroom
1 bathroom
Sleeps 4
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Island Paradise on Totem Point in the 1000 Islands, holiday rental in Wellesley Island

Island Paradise on Totem Point in the 1000 Islands

49 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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The Floating Cottage 'On the Rocks' at the Swan Bay Resort, holiday rental in Wellesley Island

The Floating Cottage 'On the Rocks' at the Swan Bay Resort

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New 1000 Islands-Murray Isle Cottage, holiday rental in Wellesley Island

New 1000 Islands-Murray Isle Cottage

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront Wellesley Island Apt w/ Private Dock!, holiday rental in Wellesley Island

Waterfront Wellesley Island Apt w/ Private Dock!

1 bedroom
1 bathroom
Sleeps 4
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SPECIAL OFFER THIS WEEK! WATERFRONT GEM! Private,3 Acres, River + Castle Views!, holiday rental in Wellesley Island

SPECIAL OFFER THIS WEEK! WATERFRONT GEM! Private,3 Acres, River + Castle Views!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Paddles on the Porch, holiday rental in Wellesley Island

Paddles on the Porch

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Casablanca Historic Island Mansion on Cherry island, holiday rental in Wellesley Island

Casablanca Historic Island Mansion on Cherry island

14 bedrooms
8 bathrooms
Sleeps 28
Match: Sleeps
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Schooner’s on the Bay, holiday rental in Wellesley Island

Schooner’s on the Bay

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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1000 Islands Retreat-Stunning Views! River Access for a boat., holiday rental in Wellesley Island

1000 Islands Retreat-Stunning Views! River Access for a boat.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Watermark Luxe Waterfront Cottages - Skye, holiday rental in Wellesley Island

Watermark Luxe Waterfront Cottages - Skye

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Tekdiv B & B, holiday rental in Wellesley Island

Tekdiv B & B

3 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Waterfront Cottage on Grindstone Island Thousand Islands New York, holiday rental in Wellesley Island

Beautiful Waterfront Cottage on Grindstone Island Thousand Islands New York

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Townhome w/ Attached Boathouse on Alexandria Bay!, holiday rental in Wellesley Island

Townhome w/ Attached Boathouse on Alexandria Bay!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Island Rental, holiday rental in Wellesley Island

Private Island Rental

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Charming Island Right on the St Lawrence River, holiday rental in Wellesley Island

Charming Island Right on the St Lawrence River

5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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1000 Islands Great Camp Island Retreat available for the 2019 rental season, holiday rental in Wellesley Island

1000 Islands Great Camp Island Retreat available for the 2019 rental season

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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The Ledges Resort & Marina, holiday rental in Wellesley Island

The Ledges Resort & Marina

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Private Island in the beautiful Thousand Islands, St Lawrence River, holiday rental in Wellesley Island

Private Island in the beautiful Thousand Islands, St Lawrence River

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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