Holiday houses in Wellesley Island

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Top-rated holiday rentals in Wellesley Island

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Guest favourite
A spacious bedroom is furnished with a wooden bed frame and a comfortable mattress. A light-colored quilt lays against the bedding. A wooden dresser and decorative wall elements provide additional character, while a doorway leads to another area of the suite.
Apartment in Clayton
4.97 out of 5 average rating, 39 reviews

Island Bayside Waterfront Suite

Our one of a kind location is nested right on the edge of the Village of historic Clayton, our downstairs studio style suite overlooks our waterfront lawn and dock area, unique with great views and centrally located right in the heart of the 1000 islands area. New from top to bottom with all amenities and outdoor deck and patio, dockage right in front available, a boaters dream! King size bedroom with Full kitchenette with all the essentials with Sleeper couch living area with modern amenities!

Top Guest favourite
A master bedroom features a queen-size bed with a textured white coverlet. Large windows and sliding glass doors allow for natural light and offer views of the waterfront. A small table is positioned near the window for additional functionality.
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
Large sliding glass doors offer views of the St. Lawrence River, allowing natural light to fill the room. A spacious wooden deck extends from the interior, providing an outdoor area for relaxation. The tranquil water reflects the blue sky, enhancing the serene environment.
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.

Top Guest favourite
A timber frame cabin is set among lush greenery, featuring a spacious porch with a metal roof and an American flag displayed. The entrance is surrounded by natural stone and a well-maintained lawn, complementing the tranquil woodland atmosphere.
Cabin in Wellesley Island
5 out of 5 average rating, 26 reviews

The Dream - Serene Lakehouse on Wellesley Island

Escape the hustle and bustle of everyday life at this beautiful lakefront home hidden away on Wellesley Island in Lake of the Isles. The timber frame cabin is affectionately named “The Dream” because it is exactly that! Experience the magic of St. Lawrence River life. Enjoy watching beautiful sunsets from the stunning porch with lakefront views. Relax with a good book, coffee, games, or water activities. The property offers everything you need for a memorable getaway with family or friends!

Guest favourite
The cabin is situated on a gently sloping green lawn surrounded by trees. A spacious deck is visible, complemented by outdoor furniture. A landscaped area with stone walls and plants can be seen in the foreground, enhancing the natural setting.
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.

Top Guest favourite
The guest room features two twin beds made with rustic log frames, accented by patterned throws. Light wood paneling covers the walls, and a ceiling fan hangs above. A small nightstand is placed beside one bed, with a lamp and decorative items displayed.
Guesthouse in Chaumont
4.99 out of 5 average rating, 127 reviews

Peaceful Getaway

Kick back and relax in this peaceful space. Guest house has two twin beds, private bathroom, microwave, toaster, Keurig, small refrigerator. WiFi access, outdoor grill with outdoor dining and seating area all under a 16x24 pavilion. This property offers incredible views, fish jumping and canoe and kayak access. End your incredible day fishing off the dock with s’mores at the fire pit. Hunters and fishermen welcome. Plenty of parking so bring your motorized toys! See you soon!

Top Guest favourite
Home in Clayton
5 out of 5 average rating, 29 reviews

River View Cottage

Completely remodeled 2 bedroom, 1 bathroom cottage with St. Lawrence River channel views! No water access. Fisherman’s paradise! Centrally located between the village of Clayton and Fishers Landing. Boat launch and marina only 1 mile away. 3 miles to Clayton and 7 miles to Alexandria Bay. Sleeps 6. 1 king bedroom 2 queen bedroom Fully equipped kitchen. Outdoor gas grill and patio furniture. Heat and AC, electric fireplace. Washer and Dryer. Linens and towels provided.

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
4.75 out of 5 average rating, 16 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
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!

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.

Popular amenities for Wellesley Island holiday rentals