Discover a selection of 186 vacation rentals in Wellesley Island, NY that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including gardens and backyards and swimming pools. Prices start at $108 per night, and houses and cottages are popular options for a stay in Wellesley Island. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Wellesley Island
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Destination guide

Why people love visiting historic Wellesley Island

Enjoy the history and other features of Wellesley Island. Renowned for its island views, boating and riverfront, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Things to do

Activities and attractions in and around Wellesley Island

Are you hoping to find things to do in the area? Venture out of your vacation home and check out everything that makes Wellesley Island a fun spot to vacation. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Thousand Islands Winery (1.7 mi / 2.7 km)
  • Alex Bay 500 Go-Karts (1.9 mi / 3 km)
  • Gananoque Boat Line (8.6 mi / 13.9 km)
  • Smuggler's Glen Golf Course (4.2 mi / 6.8 km)
  • The Landon Bay Centre (5.4 mi / 8.6 km)
  • Coyote Moon Vineyards (5.8 mi / 9.3 km)
Natural features

Exploring the natural features in Wellesley Island

Whether you're an active traveler or just want to take in the scenery, Wellesley Island is a great place to spend some time outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city center:

  • St. Lawrence Islands National Park (2.9 mi / 4.6 km)
  • Heart Island (3.6 mi / 5.7 km)
  • Thousand Islands National Park (3.8 mi / 6.2 km)
  • Charleston Lake Provincial Park (12.7 mi / 20.5 km)
  • Black Lake (22.5 mi / 36.2 km)
  • Scenic View Park (3.3 mi / 5.4 km)
How to get there

How to get to and around Wellesley Island

Fly into Watertown, NY (ART-Watertown Intl.), the closest airport, located 22.3 mi (35.8 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Kingston, ON (YGK-Norman Rogers), which is 31.1 mi (50.1 km) away.

What are the top vacation rentals in or near Wellesley Island?

From upmarket houses to inexpensive cottages, Vrbo has properties to fit all budgets and tastes. Pack your bags and check out these top vacation rentals in Wellesley Island:

  • "Waterfront House On Wellesley Island": This Town of Orleans retreat offers 3 bedrooms and is rated highly among guests. Amenities such as a hair dryer and a nearby waterfront help make your stay a memorable one.
  • "Tranquil, Secluded, Updated Two": Put your luggage down and your feet up at this pick of the bunch in Town of Alexandria. It comes with 4 bedrooms, a smart TV, beach towels and more.

For even more great options, use the search bar at the top of the page to find the perfect Wellesley Island vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Wellesley Island?

We all need an escape from the real world every once in a while. If you're yearning for a couple of lazy mornings in a cushy bed with a good book, you'll find some fabulous weekend getaways in and near Wellesley Island. These are some of our favorites:

  • "No River Access But A Nice View Of It" is around 2 miles southwest of Wellesley Island and will be just the thing to refresh your spirit. You'll appreciate the range of amenities here, including a stovetop and nearby ecotour services.
  • Alternatively, make memories with your loved ones at "Gorgeous Inside - Wellesley Island", which is around 3 miles to the southwest of Wellesley Island. Take advantage of a fireplace, off-street parking options and more here.

Can I find short term rentals in or near Wellesley Island?

From affordable apartments to huge vacation homes, Vrbo has your quick break sorted. Here are some of our favorite stays in and around Wellesley Island:

  • Close to the center of Wellesley Island, "Simple And Peaceful Retreat - Fully Booked 2022" welcomes short-term guests. When you're not relaxing in your comfortable digs, get out and explore all the fun stuff around you.
  • Alternatively, spend a couple of relaxing nights at "Updated Cottage In Historical Thousand Island Park". This comfy, conveniently located property makes it easy to explore the area's sights.

What are the best romantic weekend getaways in or near Wellesley Island?

Nothing says "I love you" quite like a romantic weekend together. If you'd like to spend a couple of relaxing evenings away with your honey, we've got some romantic getaways in and around Wellesley Island that will whisk you off your feet:

  • Sneak off on Friday for a couple of passionate nights at "Waterfront House On Wellesley Island". Located approximately 1 mile from Wellesley Island, it comes with plenty of nice touches, including air conditioning and a dining table.
  • Another place where you can enjoy a few idyllic days together is "Rustic House On St. Lawrence River With Million Dollar View And Dock Space". Around 1 mile from Wellesley Island, a dining table and a firepit add to the ambiance here.

What are the best houses for rent with a pool in or near Wellesley Island?

A pool is often an all-important amenity when choosing where to stay, especially if you're traveling with kids. Check out these houses with a pool in or near Wellesley Island and spend your days splish-splashing around:

  • Get into vacay mode at "Waterfront House On Wellesley Island", where your biggest priority will be relaxing by the pool. Amenities including coffee and tea making facilities and a garden help make this escape a favorite with guests.
  • "Rustic House On St. Lawrence River With Million Dollar View And Dock Space" is the type of place you go to escape from it all and make the most of your surroundings, starting with its pool. A dining table and outdoor furniture are also on hand to make your stay nice and comfy.

Don't know what to pack for your Wellesley Island break? This enticing destination has a humid continental climate. During the summer months, you can expect average temperatures of between 55 ºF and 75 ºF. Look up our selection of Wellesley Island vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more ideas about where to stay.

What are the best large family vacation rentals in or near Wellesley Island?

Privacy, comfort and space are essential to any successful family getaway, and Vrbo's range of large family vacation rentals in and around Wellesley Island offer the perfect solution. Here are a couple to get you started:

  • Located around 1 mile to the south of Wellesley Island, "Rustic House On St. Lawrence River With Million Dollar View And Dock Space" can fit up to 8 people over 5 bedrooms. As well as loads of space to sprawl out, amenities here include a microwave oven and free toiletries.
  • Another lovely home away from home is "Simple And Peaceful Retreat - Fully Booked 2022". Around 3 miles southwest of Wellesley Island, it comes with 4 bedrooms, space for up to 10 guests, a fridge and a DVD player.

Can I find two-bedroom vacation rentals in or near Wellesley Island?

Yes, you can. From cool apartments to comfortable cabins, Vrbo offers a selection of vacation rentals. Traveling families will like these two-bedroom options in or near Wellesley Island:

  • "Gorgeous Inside - Wellesley Island" is a terrific choice for smaller groups. In addition to two bedrooms, this relaxing stay offers amenities like a garden and a fireplace.
  • Another highly recommended option is "Garden At Eden" Located In Historic Thousand Island Park On Wellesley Island". With convenient amenities such as a garden and a kitchen, you'll have no trouble making yourselves at home here. Pick your favorite room, unpack your bags and let the fun begin!

What are the best three-bedroom vacation rentals in or near Wellesley Island?

Three-bedroom rentals in or near Wellesley Island give you flexibility and space to make the most out of your vacation. Take a look at some of the fantastic options available here:

  • Offering space, privacy and comfort, you'll get your entire gang's nod of approval at "Waterfront House On Wellesley Island". This stay comes with amenities including a nearby waterfront and a firepit.
  • Another superb three-bedroom rental is "No River Access But A Nice View Of It". Take advantage of a nearby river and a kitchen while spending valuable time with the people you love.

Are there vacation rentals with fire pits in or near Wellesley Island?

Whether you want to enjoy a glass of wine beside the flames with your sweetheart or simply stay toasty after the sun sets, we'll help you find a vacation rental with a fire pit. Here are some of our favorite options in or near Wellesley Island:

  • Gather with the ones you love around the open fire at "Waterfront House On Wellesley Island". A nearby waterfront and a kitchen are other conveniences to make the most of here.
  • Alternatively, let the flickering flames lull you into a state of relaxation at "Rustic House On St. Lawrence River With Million Dollar View And Dock Space". When you're not lounging around the fire pit, take advantage of conveniences like a nearby river and a firepit.