Holiday houses in Wellesley Island

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Top-rated holiday rentals in Wellesley Island

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Top Guest favourite
Cottage in Hammond
4.96 out of 5 average rating, 196 reviews

River Ledge Hideaway

New construction home designed specifically with the thought of guests in mind overlooking the Saint Lawrence River. Enjoy a memorable fall or holiday getaway to this waterfront oasis. Highlighting this home is a large master bedroom overlooking numerous islands speckled throughout the expansive water view. Outdoor fire pit and grilling area will be set up for the fall season. Walk down our path to your own private waterfront. Great place for couples, small families or friends getting together

Top Guest favourite
A comfortably furnished living area features a gray sofa and armchairs, with natural light streaming through three windows. A coffee table rests on a textured rug, complemented by a small indoor plant and framed artwork hanging on the wall.
Condo in Clayton
4.98 out of 5 average rating, 108 reviews

Cozy Boutique Condo in Historic McKinley Building

Lily Pad is the perfect vacation rental for two, in downtown historic Clayton! This “urban” zen–gem is one block from the River and the new River Walk. Walk everywhere - to restaurants ,parks, shops and museums. This 2nd story hide-away is nestled between River Yoga, Porch and Paddle, and River Rat Cheese. Off-street private parking. One bedroom, one bath queen with air-conditioning and River summer breezes. We use all-natural, organic cleaning supplies and home products whenever possible.

Guest favourite
Home in Gananoque
4.74 out of 5 average rating, 110 reviews

1000 Islands Peninsula Getaway

Welcome to the gateway of the world! Located in the beautiful Thousand Islands and a 3 minute drive downtown Gananouqe and a 20 minute drive to downtown Kingston, you are fully surrounded by the beautiful St Lawrence River. This cottage is perfectly located for you and your friends and family to enjoy. With its extra large windows this luxury but homey cottage was designed for star gazing and watching the sunset from the comfort off the living room or its beautiful 10 foot kitchen island.

Guest favourite
Cottage in Leeds and the Thousand Islands
4.92 out of 5 average rating, 234 reviews

Smugglers Getaway on the St. Lawrence River

Enjoy your privacy in this waterfront cabin in the historic Smugglers Cove on the St. Lawrence River in the heart of the 1000 Islands. You'll have use of the entire cabin with fantastic River views from your own patio. Conveniently located off of the 1000 Islands Parkway, one of the most beautiful scenic drives in North America, guests may enjoy walking, hiking and cycling the paved and scenic 37 km Waterfront Trail. You're welcome to arrive by boat or car; private entrance to your cabin.

Guest favourite
A wooden deck extends over the water, featuring a screened-in gazebo with a table and chairs. The serene lake reflects the clear sky, surrounded by trees that offer a sense of privacy. Sunlight glints off the water, enhancing the peaceful setting.
Home in Wellesley Island
5 out of 5 average rating, 10 reviews

YearRound Lake Life Waterfront Cottage & boat dock

YEAR ROUND lake loving! This secluded cottage sits directly on Lake of the Isles. Accessible by private road with plenty of parking or launch your boat at DeWolf State Park and in 30 seconds, arrive at the cottage and moor your boat during your stay. Surrounded by mature trees, you can relax and enjoy the tranquility of the lake. At the water, there is a large floating dock. You'll enjoy swimming and great fishing from the dock. Newly drilled well 12/24

Superhost
A waterfront view showcases a large freighter passing through a shimmering channel. A wooden deck extends towards the water, bordered by lush green grass. A small dock is visible to the left, providing direct water access, while trees line the far shore in the background.
Home in Wellesley Island
4.76 out of 5 average rating, 17 reviews

Beautiful Wellesley Island Home

Your family will be close to everything when you stay at this centrally-located place. Our home is located in the heart of the Thousand Islands about half way between Alexandria Bay and Clayton. There are many things to see and do in this region of Northern New York. Whether you are in the living room, kitchen, game room, or master bedroom, the views of the main shipping channel are amazing, as you will see many freighters pass by during your stay.

Top Guest favourite
The exterior of a single-story house is shown, featuring a fenced yard with a manicured lawn. A circular firepit is surrounded by several chairs in a cozy arrangement. A spacious deck is accessible from the house, offering additional seating alongside the lush greenery.
Home in Clayton
4.96 out of 5 average rating, 92 reviews

Comfy home with great river view. Pets considered.

My place is close to The St. Lawrence River between Alexandria Bay, NY and Clayton, NY, family oriented activities, wineries, shopping, dining, golfing, a short drive to Canada. You’ll love my place because of the great neighborhood with stunning views of the St. Lawrence River. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). Additional charge for pets and dock usage.

Top Guest favourite
Tiny home in Perth
4.93 out of 5 average rating, 351 reviews

Off-grid A-frame cabin, come relax in the forest!

Welcome to “The Hemlock” cabin One of two unique cabins on the property. A unique stay situated minutes from historic Perth, Ontario. The Hemlock sits on 160+ acres of private, natural forest. Enjoy 3 season lake access for kayaking & canoe. Year round trails for hiking, snow shoeing, exploring etc. Beautiful scenery and wildlife in a peaceful, private setting, relax and unwind by the fire! We look forward to having you!

Top Guest favourite
An inviting exterior view of the property features a wooden deck adorned with soft lighting. A covered seating area includes a small table and chairs, enhancing the outdoor space. Lush greenery surrounds the home, creating a tranquil setting for relaxation.
Place to stay in Spencerville
5 out of 5 average rating, 122 reviews

Honeybee Haven - Dog Friendly, Free Parking

Escape to a cozy, dog friendly haven, perfect for embracing the magic of the spring season. Nestled in a picturesque landscape, our property offers all the comforts you need for a memorable stay. Whether you’re here for adventure, romance or relaxation, Honeybee Haven is your ultimate getaway. Located minutes off of Hwy 401 and the US border crossing, an hour from both Kingston and Ottawa and two hours from Montreal.

Guest favourite
A spacious living area is highlighted by a wall of large windows overlooking a natural landscape. The comfortable seating arrangement includes a leather sofa and chairs, complemented by a coffee table and decorative elements. A flat-screen TV is mounted above a fireplace, enhancing the cozy setting.
Home in Wellesley Island
4.88 out of 5 average rating, 56 reviews

Thousand Islands Home w/ views of Boldt Castle

Check out this gorgeous Thousand Islands 4 Bed, 2.5 bath home located in Westminster park on Wellesley Island. This home features a huge living space w/ a wall of windows that provide clear views of Boldt Castle and the St Lawrence River. The home is fully equipped with kitchen items, coffee, towels, soap, wifi, board games and more. There's also plenty of parking for cars and boats and toys.

Guest favourite
Home in Lansdowne
5 out of 5 average rating, 7 reviews

Thousand Islands Waterfront Home - Top Unit

A peaceful waterfront top unit rental house located at a marina on the St. Lawrence River in the 1000 Islands. The space is simple, comfortable, and perfect for a memorable getaway close to everything you would need! Enjoy direct river access, a beautiful patio view, a fire pit and bbq for evenings by the water, and lots of fun activities and tasty restaurants nearby!

Guest favourite
A spacious wooden deck is presented, featuring a table surrounded by six chairs. A hammock hangs nearby, and vibrant sunset colors can be seen through the trees in the background. The area is bordered by safety railings, ensuring a secure environment for guests.
Cabin in Wellesley Island
4.87 out of 5 average rating, 39 reviews

Pointers Cabin, Close to Everything!

Welcome to Pointer's Cabin (named after our two German Shorthaired Pointers)! We love our little cabin in the woods and can't wait for you to enjoy it too. The house comfortably sleeps 6 and has a large yard with a spacious deck that has enclosed railings to keep pets and kids safe! The deck is the perfect spot to enjoy your morning coffee or your nightly cocktails!

Popular amenities for Wellesley Island holiday rentals