Wellesley Island Vacations
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Find the Best Wellesley Island Vacation Packages
Wellesley Island Hotel Deals
Thousand Island Hart House
21979 Club Rd Wellesley Island NY
Fully refundableReserve now, pay when you stay
￥30,250
￥33,577 total
Oct 1 - Oct 2
includes taxes & fees
9.6/10 Exceptional! (30 reviews)
"The property is a piece of the past, which is something that I love. The breakfast was delicious and the staff was great."
Reviewed on Sep 17, 2026
Private 4-Acre Retreat • Sleeps 13 • Fire Pit • Playground, 5 min to State Park
Wellesley Island NY
￥59,831
￥110,804 total
Sep 25 - Sep 26
includes taxes & fees
10/10 Exceptional! (4 reviews)
"This is an absolutely beautiful place to stay on Wellesley Island, NY. Tanya is a wonderful host - very responsive. We stayed 2 nights (Husband, wife & 18 y/o son). We really enjoyed the snack basket the host left for us - a very nice and thoughtful touch! The kitchen is well-stocked with everything ..."
Reviewed on Aug 23, 2026
Cozy Rustic Cabin - 1000 Islands Getaway
Wellesley Island NY
9.2/10 Wonderful! (15 reviews)
"Everything was perfect. Except that instead the sofa there was a queen side bed in the kitchen/living room. Anyhow not a big issue.Loved the location."
Reviewed on Aug 31, 2026
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.
Stay near popular Wellesley Island attractions
Thousand Islands Bridge
8.8/10 (627 reviews)
This scenic five-bridge system spans the Saint Lawrence River, connecting the US and Canada with stunning island views. Capture the engineering marvel and natural beauty while crossing between two countries.
Boldt Yacht House
10.0/10 (1 review)
This grand shingle-style yacht house once housed George Boldt's fleet during the Gilded Age. Inside, discover a collection of antique wooden boats that tell the maritime story of the Thousand Islands region.
Dewolf Point State Park
10.0/10 (1 review)
Tucked away on the St. Lawrence River's Lake of the Isles, Dewolf Point State Park offers a serene escape for nature lovers. Reserve a rustic cabin for a weekend of fishing, boating, and peaceful riverside relaxation.
Waterson Point State Park
10.0/10 (1 review)
This boat-access-only sanctuary offers serene docking in the heart of Thousand Islands. Enjoy shoreline fishing or picnic in the century-old gazebo while surrounded by untouched natural beauty.
Mary Island State Park
10.0/10 (1 review)
This secluded island retreat offers spectacular views of the Canadian shore from its rocky outcroppings. Accessible only by boat, campers enjoy waterfront sites and tranquil hiking trails along the St. Lawrence River.
What to do in Wellesley Island
Boldt Castle and 2 Nation Tour
￥5,123
per adult
82% of travellers recommend
The Ultimate Heart of 1000 Islands Sightseeing Boat Tour
￥13,448
per adult
94% of travellers recommend
Thousand Islands Two Castle Helicopter Tour
￥38,555
per adult
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?
- Choose your travel dates: The things you want to do in Wellesley Island and your preferred season will help you decide when to go.
- 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.
- 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.
- 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.
