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!
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
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 Yacht House and Boldt ...
Thousand Islands Home w/ views of Boldt Castle
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Waterfront 5 Bedroom Grindstone Island Farmhouse

Waterfront 5 Bedroom Grindstone Island Farmhouse

Clayton
Stay at this vacation home in Clayton. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions 1000 Islands River Rat Cheese and The Clayton ...
Waterfront 5 Bedroom Grindstone Island Farmhouse
Comfy Two Bedroom Thousand Islands Getaway

Comfy Two Bedroom Thousand Islands Getaway

Clayton
Stay at this vacation home in Clayton. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Grass Point State Park and Blind Bay are located ...
Comfy Two Bedroom Thousand Islands Getaway
Charming cottage on Chaumont Bay, pet friendly, kayaks, dock, DIRECTLY ON LAKE!

Charming cottage on Chaumont Bay, pet friendly, kayaks, dock, DIRECTLY ON LAKE!

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, DIRECTLY ON LAKE!
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 and Fishermen Welcome!

Family and Fishermen Welcome!

Chaumont
Book a stay at this family-friendly vacation home in Chaumont. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Lake Island ...
Family and Fishermen Welcome!
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 Grass Point State Park and Rock Island Lighthouse ...
Charming Waterfront House with Detached Cabin
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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
123 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Pristine Downtown Clayton Village Home Just Steps Away From Everything!, The Ledges Resort and Marina, Lighthouse, Thousand Islands Home w/ views of Boldt Castle, Waterfront 5 Bedroom Grindstone Island Farmhouse, Comfy Two Bedroom Thousand Islands Getaway, Charming cottage on Chaumont Bay, pet friendly, kayaks, dock, DIRECTLY ON LAKE!, SPRING SPECIALS! Relaxing River Oasis & Dock, Family and Fishermen Welcome!, Charming Waterfront House with Detached Cabin

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 Yacht House and Boldt ...
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
Lake of the Isles Waterfront Cottage w/ boat dock! Walk to DeWolf State Park

Lake of the Isles Waterfront Cottage w/ boat dock! Walk to DeWolf State Park

Wellesley Island
Stay at this cottage in Wellesley Island. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Dewolf Point State Park and Waterson Point State ...
Lake of the Isles Waterfront Cottage w/ boat dock! Walk to DeWolf State Park
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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 Dewolf Point State Park ...
Family-Friendly Cabins on 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.