Wellesley Island Vacations

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Find the Best Wellesley Island Vacation Packages

Wellesley Island Hotel Deals

Thousand Island Hart House

Thousand Island Hart House

2 out of 5
21979 Club Rd Wellesley Island NY
9.4/10 Exceptional! (38 reviews)
"Room was clean comfortable, staff were great breakfast was amazing"

Reviewed on 6 November 2026

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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 27 August 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. Itā€™s sounds like a helicopter."

Reviewed on 9 October 2026

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Thousand Islands Country Club
See all 411 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.

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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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 traveling in January, February and March. You'll usually find better rates on airfares and hotels during these months ā€” perfect for a budget-friendly break.
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 travelers 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, favorite 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.