Wellesley Island Vacation Packages

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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.

Top Wellesley Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Watertown Fort Drum

Days Inn by Wyndham Watertown Fort Drum

2 out of 5
Price was CA $576, price is now CA $532 per person
CA $532
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Kingston (YGK) to Watertown (ART)
8.8/10 Excellent! (1,005 reviews)
Nice and quiet with reasonable rates.

Reviewed on Jul 2, 2026

Chateau Country Inn

Chateau Country Inn

2 out of 5
Price was CA $664, price is now CA $632 per person
CA $632
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Kingston (YGK) to Watertown (ART)
9.6/10 Exceptional! (153 reviews)
Room was spotless, breakfast was just what we e, parking was right in front of the door and Dede and her staff were wonderful.

Reviewed on Jun 29, 2026

The GillHouse

The GillHouse

2 out of 5
Price was CA $1,800, price is now CA $1,722 per person
CA $1,722
per person
Aug 2 - Aug 5
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Watertown (ART)
9.8/10 Exceptional! (11 reviews)
Very accommodating restaurant staff was super friendly

Reviewed on Jul 3, 2026

Thousand Island Hart House

Thousand Island Hart House

2 out of 5
Price was CA $999, price is now CA $960 per person
CA $960
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Kingston (YGK) to Watertown (ART)
9.8/10 Exceptional! (22 reviews)

Quality Inn & Suites Watertown Fort Drum

Quality Inn & Suites Watertown Fort Drum

2.5 out of 5
Price was CA $1,557, price is now CA $1,510 per person
CA $1,510
per person
Aug 2 - Aug 5
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Watertown (ART)
8.2/10 Very good! (1,001 reviews)
Service was poor and there is too less items in breakfast. It’s better to not to provide breakfast. Horrible experience and not recommended.

Reviewed on Jul 1, 2026

Ready to book your vacation to Wellesley Island?

 

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Stay near popular Wellesley Island attractions

Thousand Islands Bridge

8.8/10 (627 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.
See properties

What to do in Wellesley Island

The Ultimate Heart of 1000 Islands Sightseeing Boat Tour

The Ultimate Heart of 1000 Islands Sightseeing Boat Tour

CA $115
per adult
94% of travellers recommend
The Ultimate Heart of 1000 Islands Sightseeing Boat Tour
1000 Islands

Thousand Islands Helicopter Tour

CA $132
per adult
100% of travellers recommend
Thousand Islands Helicopter Tour
Tour to Niagara, Toronto, Washington, Amish, Philadelphia and NYC

5 Days-Perfect East

CA $1,363
per adult
100% of travellers recommend
5 Days-Perfect East
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 from CA $532 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.

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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.