Book Holiday Homes in Wellesley Island

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Featured Holiday Homes in Wellesley Island

Pristine Downtown Clayton Village Home Just Steps Away From Everything!

Pristine Downtown Clayton Village Home Just Steps Away From Everything!

Clayton
Stay at this vacation home in Clayton. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Thousand Islands Museum and 1000 Islands River ...
Pristine Downtown Clayton Village Home Just Steps Away From Everything!
Charming 3-bedroom, newly remodeled house in the heart of Clayton, NY

Charming 3-bedroom, newly remodeled house in the heart of Clayton, NY

2 out of 5
Clayton
Stay at this vacation home in Clayton. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Antique Boat Museum and Thousand Islands ...
Charming 3-bedroom, newly remodeled house in the heart of Clayton, NY
The Ledges Resort and Marina, Lighthouse

The Ledges Resort and Marina, Lighthouse

Alexandria Bay
Stay at this vacation home in Town of Alexandria. Enjoy a garden, balconies, and cable/satellite TV service. Popular attractions Lil' River Fudge Co / 5&10 Variety ...
The Ledges Resort and Marina, Lighthouse
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Thousand Islands Home w/ views of Boldt Castle

Thousand Islands Home w/ views of Boldt Castle

Wellesley Island
Book a stay at this family-friendly vacation home in Wellesley Island. Enjoy free WiFi, a garden, and patios. Popular attractions Boldt Castle and Boldt Yacht ...
Thousand Islands Home w/ views of Boldt Castle
Charming cottage on Chaumont Bay, pet friendly, kayaks, dock, ICE FISHING

Charming cottage on Chaumont Bay, pet friendly, kayaks, dock, ICE FISHING

Chaumont
Stay at this vacation home in Chaumont. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Lake Island and Long Point State Park - Thousand ...
Charming cottage on Chaumont Bay, pet friendly, kayaks, dock, ICE FISHING
Riverfront Retreat: Dock access & Tanker Views

Riverfront Retreat: Dock access & Tanker Views

Alexandria Bay
Book a stay at this family-friendly vacation home in Alexandria Bay. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Thousand Islands ...
Riverfront Retreat: Dock access & Tanker Views
Visit Us For The Best View Of The Thousand Islands

Visit Us For The Best View Of The Thousand Islands

Clayton
Stay at this vacation home in Clayton. Enjoy a garden, tennis courts, and patios. Popular attractions Clayton Marina and The Clayton Opera House are located ...
Visit Us For The Best View Of The Thousand Islands
Charming Waterfront House with Detached Cabin

Charming Waterfront House with Detached Cabin

Clayton
Stay at this vacation home in Clayton. Enjoy patios, in-room fireplaces, and air conditioning. Popular attractions Boldt Castle and Grass Point State Park are ...
Charming Waterfront House with Detached Cabin
Super Clean, Pet Friendly Cottage! 3 Bedroom! NO EXTRA FEES!!

Super Clean, Pet Friendly Cottage! 3 Bedroom! NO EXTRA FEES!!

Alexandria Bay
Stay at this vacation home in Alexandria Bay. Enjoy free WiFi, a garden, and patios. Popular attractions Lil' River Fudge Co / 5&10 Variety Store and Heart Island ...
Super Clean, Pet Friendly Cottage! 3 Bedroom! NO EXTRA FEES!!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Wellesley Island Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Wellesley Island vacation homes are the perfect way for you to wing it.

Holiday houses in Wellesley Island let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Wellesley Island in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Wellesley Island adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Wellesley Island with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Wellesley Island vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Wellesley Island Holiday Homes essential information

Accommodation
126 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Pristine Downtown Clayton Village Home Just Steps Away From Everything!, Charming 3-bedroom, newly remodeled house in the heart of Clayton, NY, The Ledges Resort and Marina, Lighthouse, Thousand Islands Home w/ views of Boldt Castle, Charming cottage on Chaumont Bay, pet friendly, kayaks, dock, ICE FISHING, Riverfront Retreat: Dock access & Tanker Views, Visit Us For The Best View Of The Thousand Islands, Charming Waterfront House with Detached Cabin, Super Clean, Pet Friendly Cottage! 3 Bedroom! NO EXTRA FEES!!

Top trending hotels in Wellesley Island

Thousand Islands Home w/ views of Boldt Castle

Thousand Islands Home w/ views of Boldt Castle

Wellesley Island
Book a stay at this family-friendly vacation home in Wellesley Island. Enjoy free WiFi, a garden, and patios. Popular attractions Boldt Castle and Boldt Yacht ...
Thousand Islands Home w/ views of Boldt Castle
SPRING SPECIALS! Relaxing River Oasis & Dock

SPRING SPECIALS! Relaxing River Oasis & Dock

Wellesley Island
Stay at this vacation home in Wellesley Island. Enjoy a garden, patios, and in-room jetted tubs. Popular attractions Boldt Yacht House and Boldt Castle are located ...
SPRING SPECIALS! Relaxing River Oasis & Dock
Family-Friendly Cabins on Wellesley Island

Family-Friendly Cabins on Wellesley Island

Wellesley Island
Book a stay at this family-friendly vacation home in Wellesley Island. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Boldt Castle and Dewolf ...
Family-Friendly Cabins on Wellesley Island
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Ice fishing!  YEAR ROUND Lake of the Isles Waterfront Cottage & boat dock!

Ice fishing! YEAR ROUND Lake of the Isles Waterfront Cottage & boat dock!

Wellesley Island
Stay at this cottage in Wellesley Island. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Boldt Castle and Dewolf Point State Park are ...
Ice fishing! YEAR ROUND Lake of the Isles Waterfront Cottage & boat dock!
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See all available properties in Wellesley Island
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.