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.

Discover the most popular places to visit in Wellesley Island

Thousand Islands Bridge

4.5/5(182 reviews)

Learn about the local history of Wellesley Island when you spend time at Thousand Islands Bridge. Stroll along the riverfront or seek out the local tours.

Thousand Islands Bridge

Boldt Yacht House

Learn about the local history of Wellesley Island with a stop at Boldt Yacht House. Amble around the area's riverfront or seek out the local tours.

Boldt Yacht House

Mary Island State Park

Commune with nature and explore the great outdoors at Mary Island State Park during your travels in Wellesley Island. Stroll along the riverfront or seek out the local tours.

Mary Island State Park

What to do in Wellesley Island

Hornblower Boat Cruise

Toronto, Niagara Falls & Thousand Islands 3–DAY Trip

$544
per adult
Toronto, Niagara Falls & Thousand Islands 3–DAY Trip
1000 Islands

Thousand Islands Helicopter Tour

$96
per adult
100% of travellers recommend
Thousand Islands Helicopter Tour
Soar over Boldt & Singer Castles!

Thousand Islands Two Castle Helicopter Tour

$243
per adult
Thousand Islands Two Castle Helicopter Tour
See all activities in Wellesley Island

Wellesley Island Hotel Deals

Cozy Rustic Cabin - 1000 Islands Getaway

Cozy Rustic Cabin - 1000 Islands Getaway

Wellesley Island
10/10 Exceptional! (3 reviews)
"Great time."

Reviewed on Aug 18, 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
$250 nightly
The price is $278 total per night from Aug 27 to Aug 28
$278 total
Aug 27 - Aug 28
Total with taxes and fees
9.6/10 Exceptional! (13 reviews)
"The Hart Hotel was perfect for us. We wanted a relaxing stay while visiting the Thousand Islands for the first time. The proprietor, Jamie, gave us a few recommendations on places to go. Everything he pointed us to was exactly what we needed...and didn't even know it. His recommendations on dining, ..."

Reviewed on Aug 11, 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 412 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.

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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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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