Wellesley Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by AMANDA

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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.

Ready to book your vacation to Wellesley Island?

 

Choose your dates

Wellesley Island Hotel Deals

Thousand Island Hart House
Thousand Island Hart House
2 out of 5
21979 Club Rd, Wellesley Island, NY
The price is CA $461 per night from Jul 8 to Jul 9
CA $461
CA $511 total
Jul 8 - Jul 9
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
Cozy Rustic Cabin - 1000 Islands Getaway
Cozy Rustic Cabin - 1000 Islands Getaway
Wellesley Island
Get rates
Cozy Rustic Cabin - 1000 Islands Getaway
Spacious Peaceful home in the Woods on Wellesley Island
Spacious Peaceful home in the Woods on Wellesley Island
Wellesley Island
9.8/10 Exceptional! (12 reviews)
Great stay
"Beautiful location, beautiful house. Owners were responsive to questions and the house was well stocked with everything we could need."

Reviewed on Jun. 23, 2025

Get rates
Spacious Peaceful home in the Woods on Wellesley Island
See all 410 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Wellesley Island

Thousand Islands Bridge

4.5/5(280 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

What to do in Wellesley Island

Hornblower Boat Cruise

Toronto, Niagara Falls & Thousand Islands 3–DAY Trip

CA $750
per adult
Toronto, Niagara Falls & Thousand Islands 3–DAY Trip
1000 Islands

Thousand Islands Helicopter Tour

CA $132
per adult
Thousand Islands Helicopter Tour
Soar over Boldt & Singer Castles!

Thousand Islands Two Castle Helicopter Tour

CA $335
per adult
Thousand Islands Two Castle Helicopter Tour
See all activities in Wellesley Island

Frequently asked questions

How much does a Wellesley Island vacation package cost?
You can grab a vacation package to this popular destination on Expedia. But how much your vacation to Wellesley Island costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Wellesley Island?
If you're hoping to book a cheap Wellesley Island vacation package, consider travelling in January, February and March. You'll usually find better rates on airfares and hotels during these months --- perfect for a budget-friendly break.
How many days is enough for Wellesley Island?
For a Wellesley Island vacation, a few days will be enough to explore the highlights. Be sure to check out Waterson Point State Park --- it's one of the most popular sights in this destination. If you want more activities, consider basing yourself here and setting off on some trips from Wellesley Island.
Is it worth booking a vacation package to Wellesley Island?
Well known for its camping, watersports and hiking, a Wellesley Island vacation offers something for everyone. Be sure to visit main sights like Dewolf Point State Park and Waterson Point State Park, and consider renting some wheels for day trips to experience even more.
How to find the best Wellesley Island package deals?
Use Expedia's filter tool to find some of the best Wellesley Island package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Wellesley Island package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Wellesley Island vacation as a package?
You can enjoy significant savings on your Wellesley Island break by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Wellesley Island?
Score incredible discounts by booking your flights in advance with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Wellesley Island break.
How to plan a trip to Wellesley Island?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Wellesley Island.
  2. Set a budget: Consider costs such as flights, transportation and food when calculating how much to set aside for your trip to Wellesley Island. Then, choose a property that matches your budget, whether that's an economical option or a high-end retreat.
  3. Decide how long to go away for: Now that you're more familiar with Wellesley Island, you can figure out the perfect length of your break. Put together a draft plan and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a tailored Wellesley Island vacation package.

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