Wellesley Island Vacations

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Your Wellesley Island Vacation

When a city getaway is calling, answer it with a vacation package to Wellesley Island. The neighborhood of Thousand Island Park, which is great for history, watersports and cycling, makes a terrific base for your adventures. If taking in sights is part of the plan during your trip to Wellesley Island, visit well-known attractions like Boldt Castle, Mary Island State Park and Dewolf Point State Park. Whatever your travel plans or budget, organizing a tailored Wellesley Island vacation is a breeze with Expedia.

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.
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What to do in Wellesley Island

1000 Islands

Thousand Islands Helicopter Tour

$93
per adult
100% of travellers recommend
Thousand Islands Helicopter Tour
Soar over Boldt & Singer Castles!

Thousand Islands Two Castle Helicopter Tour

$237
per adult
100% of travellers recommend
Thousand Islands Two Castle Helicopter Tour
See all activities in Wellesley Island

Wellesley Island Hotel Deals

Thousand Island Hart House

Thousand Island Hart House

2 out of 5
21979 Club Rd Wellesley Island NY
$250 nightly
The price is $278 total per night from Oct 28 to Oct 29
$278 total
Oct 28 - Oct 29
Total with taxes and fees
Thousand Island Hart House
Private Cabin in the Woods-Close to all amenities

Private Cabin in the Woods-Close to all amenities

Wellesley Island NY
10/10 Exceptional! (9 reviews)
"Great stay as always. Come every year"

Reviewed on Aug 27, 2026

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Private Cabin in the Woods-Close to all amenities
Thousand Islands Country Club

Thousand Islands Country Club

3 out of 5
46433 County Rd 100 Wellesley Island NY
6/10 (1 review)
"The staff are very friendly and helpful. The golf course is in good condition. No extra charge for warm up balls. The heater are way too noisy. It’s sounds like a helicopter."

Reviewed on Oct 9, 2026

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Thousand Islands Country Club
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.

Find the Best Wellesley Island Vacation Packages

Wellesley Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Watertown Intl. Airport (ART)
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Boldt Castle, Thousand Islands Winery and Coyote Moon Vineyards

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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're looking to score a cheap Wellesley Island vacation package, consider planning a trip in November, December and January. You'll generally find better rates on airfares and hotels during these quieter months — perfect for a budget-friendly break.
How many days is enough for Wellesley Island?
Usually, a few days is enough for a Wellesley Island vacation. With a well-organized itinerary, you can see all the best attractions like Waterson Point State Park, as well as explore some hidden treasures along the way.
Is it worth booking a vacation package to Wellesley Island?
Popular for its camping, watersports and hiking, a Wellesley Island vacation offers something for everyone. Be sure to check out key sights like Dewolf Point State Park and Waterson Point State Park, and consider renting a car for day trips to discover even more.
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. Pick the best time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to go to Wellesley Island.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and meals to airfares and activities. Your accommodations will probably be the biggest expense during your trip to Wellesley Island.
  3. Organize your Wellesley Island escape with Expedia's trip planning tool: Search for and book hotels and things to do all in one place. You can also collaborate with your group to plan an unforgettable trip to Wellesley Island together.
  4. Decide how long to go for: Now that you're more familiar with Wellesley Island, you can work out the perfect length of your break. Pull together a rough itinerary and allocate enough time to get through everything on your must-do list.
  5. Bundle your accommodations and airfare: Once you've nailed down your travel dates and duration, book the perfect Wellesley Island vacation package for you.
  6. Add on excursions and experiences: Have a look at our dedicated travel guide to find some exciting things to do in Wellesley Island in Wellesley Island. Book tickets or make reservations in advance to save time and avoid the stress of trying to find activities when you arrive.

Does Expedia offer Book Now, Pay Later Wellesley Island vacation packages?
If you're anything like us, you love going away but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Wellesley Island vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you spot them.

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