Wellesley Island Vacations from $591
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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.
The Latest Wellesley Island vacation packages
Price found within the past 48 hours. Click for updated prices.
Pleasant Night Inn Carthage Near Fort Drum
West Carthage
$591
per person
Oct 1 - Oct 3
just found
Roundtrip flight included
Newport News (PHF) to Watertown (ART)
7.4/10 Good! (234 reviews)
Attendant was rude. Hotel smelled awful and strange. The whole place felt dingy, weird and unwelcoming. Don't stay here unless it is your only option
Reviewed on Aug 25, 2026
Thousand Island Hart House
$722
per person
Oct 1 - Oct 3
just found
Roundtrip flight included
Newport News (PHF) to Watertown (ART)
9.8/10 Exceptional! (23 reviews)
Loved it as a base for exploring the 1000 Isls. and propietor is very helpful, friendly and full of interesting information about the area
Reviewed on Aug 27, 2026
The Roxy Cape Vincent
$682
per person
Oct 1 - Oct 3
just found
Roundtrip flight included
Newport News (PHF) to Watertown (ART)
9/10 Wonderful! (60 reviews)
Stayed for a wedding weekend and the hotel was perfect ! Super cute town right outside of the Roxy’s doors. The bed was one of the most comfortable hotel beds I’ve ever slept in. Would definitely stay again!
Reviewed on Aug 25, 2026
Quality Inn & Suites Watertown Fort Drum
$606
per person
Oct 1 - Oct 3
just found
Roundtrip flight included
Newport News (PHF) to Watertown (ART)
8.2/10 Very Good! (1,006 reviews)
Everyone was incredibly helpful, but I have to admit there was no variation in breakfast at all, and the rooms are old, my desk chair needed some love.
Reviewed on Aug 28, 2026
Don't see what you're looking for?
See all available trips from Columbus to Wellesley Island
View all tripsStay 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.
Boldt Yacht House
10.0/10 (1 review)
This grand shingle-style yacht house once housed George Boldt's fleet during the Gilded Age. Inside, discover a collection of antique wooden boats that tell the maritime story of the Thousand Islands region.
Waterson Point State Park
10.0/10 (1 review)
This boat-access-only sanctuary offers serene docking in the heart of Thousand Islands. Enjoy shoreline fishing or picnic in the century-old gazebo while surrounded by untouched natural beauty.
Mary Island State Park
10.0/10 (1 review)
This secluded island retreat offers spectacular views of the Canadian shore from its rocky outcroppings. Accessible only by boat, campers enjoy waterfront sites and tranquil hiking trails along the St. Lawrence River.
Dewolf Point State Park
10.0/10 (1 review)
Tucked away on the St. Lawrence River's Lake of the Isles, Dewolf Point State Park offers a serene escape for nature lovers. Reserve a rustic cabin for a weekend of fishing, boating, and peaceful riverside relaxation.
What to do in Wellesley Island
Thousand Islands Helicopter Tour
$90
per adult
100% of travellers recommend
The Ultimate Heart of 1000 Islands Sightseeing Boat Tour
$84
per adult
94% of travellers recommend
Wellesley Island Hotel Deals
Thousand Island Hart House
21979 Club Rd Wellesley Island NY
Fully refundableReserve now, pay when you stay
$232 nightly
$258 total
Sep 3 - Sep 4
Total with taxes and fees
9.8/10 Exceptional! (26 reviews)
"Loved it as a base for exploring the 1000 Isls. and propietor is very helpful, friendly and full of interesting information about the area"
Reviewed on Aug 27, 2026
Cozy Rustic Cabin - 1000 Islands Getaway
Wellesley Island NY
9.2/10 Wonderful! (14 reviews)
"It meets basic needs. But there were two adults and one teenager and two dogs. Very very tight space. No dresser or anywhere to put anything up off the floor besides a small coffee bar. Bed in living room was the hardest thing I have ever slept on in my life. May as well have been a marble countertop. ..."
Reviewed on Aug 20, 2026
Private 4-Acre Retreat • Sleeps 13 • Fire Pit • Playground, 5 min to State Park
Wellesley Island NY
$591 nightly
$656 total
Sep 1 - Sep 2
Total with taxes and fees
10/10 Exceptional! (4 reviews)
"This is an absolutely beautiful place to stay on Wellesley Island, NY. Tanya is a wonderful host - very responsive. We stayed 2 nights (Husband, wife & 18 y/o son). We really enjoyed the snack basket the host left for us - a very nice and thoughtful touch! The kitchen is well-stocked with everything ..."
Reviewed on Aug 23, 2026
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 from $591 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?
- 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.
- 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.
- 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.
- 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.
- Bundle your accommodations and airfare: Once you've nailed down your travel dates and duration, book the perfect Wellesley Island vacation package for you.
- 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
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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.
