Wellesley Island Vacations

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Find the Best Wellesley Island Vacation Packages

Wellesley Island Hotel Deals

Cozy Rustic Cabin - 1000 Islands Getaway

Cozy Rustic Cabin - 1000 Islands Getaway

Wellesley Island
10/10 Exceptional! (3 reviews)
"The cabin was very clean and air conditioned. It was very refreshing to come back after a hot day out on the water."

Reviewed on Jul 30, 2025

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Cozy Rustic Cabin - 1000 Islands Getaway
Thousand Island Hart House

Thousand Island Hart House

2 out of 5
21979 Club Rd, Wellesley Island, NY
The price is ￥28,542 per night from Sep 3 to Sep 4
￥28,542
￥31,682 total
Sep 3 - Sep 4
includes taxes & fees
10/10 Exceptional! (9 reviews)
Beautiful, quiet comfortable property
"Lovely room with working gas fireplace. Bed was very comfortable. Service was fantastic from start to finish. They took extra care with our room and really took care of us for breakfast. It was cooked to order both days, and delicious! Kudos to Vicky and Hannah. Area was walkable as well, and very ..."

Reviewed on Jun 18, 2025

Thousand Island Hart House
Thousand Islands Home w/ views of Boldt Castle

Thousand Islands Home w/ views of Boldt Castle

Wellesley Island
9.2/10 Wonderful! (30 reviews)
Beautiful View
"Great communication and parklike atmosphere.Well stocked down to the spices and kitchen cupboards. The location was very private and secluded. Great stay ! Thank you!"

Reviewed on Jun 3, 2025

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Thousand Islands Home w/ views of Boldt Castle
See all 415 properties in Wellesley Island
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.

What to do in Wellesley Island

Hornblower Boat Cruise

Toronto, Niagara Falls & Thousand Islands 3–DAY Trip

￥80,449
per adult
Toronto, Niagara Falls & Thousand Islands 3–DAY Trip
1000 Islands

Thousand Islands Helicopter Tour

￥14,170
per adult
Thousand Islands Helicopter Tour
Toronto, Niagara Falls & Thousand Islands VIP 2–Day Trip

Toronto, Niagara Falls & Thousand Islands VIP 2–Day Trip

￥61,141
per adult
Toronto, Niagara Falls & Thousand Islands VIP 2–Day Trip
See all activities in Wellesley Island

Frequently asked questions

How much does a Wellesley Island vacation package cost?
You can snap up a vacation package to this destination on Expedia. However, how much your vacation to Wellesley Island costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Wellesley Island?
If you'd like to book a cheap Wellesley Island vacation package, consider visiting in January, February and March. You'll typically find better prices on airfares and hotels during these months — perfect for budget-conscious travelers.
How many days is enough for Wellesley Island?
Generally, a handful of days is ideal for a Wellesley Island vacation. With a detailed itinerary, you can check out all the major attractions like Waterson Point State Park, as well as discover some hidden treasures along the way.
Is it worth booking a vacation package to Wellesley Island?
Wellesley Island has everything you need for a fantastic break — camping, watersports and hiking are just the start. Whether you want to check out attractions such as Dewolf Point State Park and Waterson Point State Park, or venture off the beaten track, there's plenty to explore on your Wellesley Island vacation.
How to find the best Wellesley Island package deals?
Start your search for a Wellesley Island package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Wellesley Island package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Wellesley Island escape underway.
Is it cheaper to book a Wellesley Island vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking hotels and flights individually. Better still, you can customize your Wellesley Island escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Wellesley Island?
Land fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Wellesley Island adventure.
How to plan a trip to Wellesley Island?

  1. Choose your travel dates: The things you want to do in Wellesley Island and your preferred season will help you decide when to go.
  2. Set a budget: Factor in costs like flights, meals and transportation when calculating how much to set aside for your trip to Wellesley Island. Then, pick a property that fits your budget, whether that's a low-cost stay or a more luxurious retreat.
  3. Decide how long to go for: Now that you're more familiar with Wellesley Island, you can figure out the perfect length of your break. Put together a draft itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your accommodations and airfare: Once you've nailed down your travel dates and duration, book the right Wellesley Island vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.