Holiday houses in Cherry Island

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Top-rated holiday rentals in Cherry Island

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Top Guest favourite
A newly renovated boathouse bunkie is shown, featuring an upper level accessible by a wooden staircase. The exterior is painted in a dark hue with white trim. Outdoor furniture and bicycles are visible near the entrance, set against a wet concrete surface reflecting the cloudy sky.
Place to stay in Mallorytown
5 out of 5 average rating, 23 reviews

Boathouse bunkie overlooking the St. Lawrence

Newly renovated boathouse bunkie overlooking the beautiful St. Lawrence River located in the Heart of the 1000 Islands. Nestled in the quaint village of Rockport. This upper level bachelor bunkie sleeps 2 in the open concept room. Separate bathroom with large shower. Kitchenette includes fridge, microwave and air fryer/toaster oven combo. You can either sit on the south deck overlooking a marina to enjoy your morning coffee or evening cocktail. Out on the north deck you can BBQ a delicious meal.

Top Guest favourite
The house is set against a clear blue sky, surrounded by a snow-covered yard. Evergreen trees and a white picket fence frame the home, highlighting its rural setting. The metal roof and large front windows create a welcoming appearance.
Cottage in Lisbon
4.97 out of 5 average rating, 62 reviews

Gracie’s Meadow House with beautiful views

The house can sleep up to 6 guests in this relaxing, quiet, rural setting. You are in close proximity to four colleges, the Canadian Border, St. Lawrence River and Adirondack Mountains. Enjoy leaf peeping, outdoor recreation, Maple Weekend events and fishing tournaments . View spring and fall bird migration at wetlands, rivers and woods nearby. Our local Amish community dots the rural roads with their locally made products. This site accommodates boat trailers and campers for easy turn around.

Top Guest favourite
An aerial view captures a single-story house next to a serene river, surrounded by lush green grass and tall reeds. A wooden deck extends from the house, leading to a private dock, which provides easy river access.
Home in Clayton
5 out of 5 average rating, 22 reviews

River Time

Relax with the whole family at this peaceful place to stay. River Time sleeps six and has an open concept main living area. Nature and tranquility abound with water views from every window. From relaxing on the huge wrap around porch to fishing on the dock or swinging in the hammock, the property will provide restorative comfort. There is wonderful natural light throughout the house. Located directly on Blind Bay in Clayton we are 7 min from the village of Clayton and 13 min to Alexandria Bay.

Guest favourite
The exterior of the home features a welcoming porch adorned with flowers. A paved pathway leads to the entrance, while a well-maintained yard is visible, bordered by natural landscaping. Two seating arrangements are positioned near the house, providing a pleasant spot to relax outdoors.
Home in Wellesley Island
4.88 out of 5 average rating, 75 reviews

Cheerful, private home with firepit

Have fun with the whole family at this spacious, newly furnished home. This single level, accessible house sleeps up to 6 people comfortably. Enjoy a large, private yard with a firepit and adirondack chairs. Sip on coffee on the cozy patio. Conveniently located between Clayton and Alexandria Bay, 4 MI from the Canadian border, close to hiking trails, swimming, boat launches, golf courses, grocery shopping, and more. Enjoy all the Thousand Islands has to offer in this comfortable, stylish home.

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
4.97 out of 5 average rating, 175 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
The exterior of a modern river house is presented, featuring a sloped roof and large windows that invite natural light. A patio with seating arrangements is visible, fronted by a grassy area. A stone pathway leads from the yard to the water's edge.
Home in Alexandria Bay
5 out of 5 average rating, 16 reviews

Welcome to our River House - 3Br

Welcome to our River House! Used mostly by our family and friends, we're offering available dates to courteous families and others who will treat it like their own. Relaxation at its finest. This is off a very private and quiet dead end road tucked on the inside of Swan Bay. Watch the Swans over your morning coffee from the patio, launch those kayaks right from our front yard, or throw that fishing line in off the shared dock (shallow). 3 Br - Queen, 2 Queen Bunks, Queen master 2.5 Bath

Top Guest favourite
The exterior entrance features a set of steps leading to a white front door, flanked by large windows for natural light. The surrounding area displays a small garden with greenery and flowers, contributing to a welcoming approach.
Apartment in Redwood
4.93 out of 5 average rating, 177 reviews

A Simple Roof

THIS IS NOT A VACATION HOME. Self-check-in/check-out. Old-fashioned, rustic apartment, painted wood floors, full kitchen, mud room, screened porch; boat/ATV parking; tent space. Ready for year-round outdoor sports, fishing, boating, biking, family camping trips. Near 1000 Islands, several lakes/waterways, 5 room apartment is one side of host duplex, 3 private entrances. King bed, 1 twin upstairs, 2 folding cots, comfy couch for sleep. Bathroom downstairs. WIFI; FireTV, HDMI cord; TVs w/DVD.

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, 231 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.

Superhost
Cabin in Leeds and the Thousand Islands
4.88 out of 5 average rating, 130 reviews

A-frame Cottage Lakeside, Charleston lake

Welcome to Minnow Cottage, the perfect place to enjoy the lake and nature, spend quality time with loved ones, and relax and recharge! Imagine peaceful mornings on the deck with coffee serenaded by the lake's loons. Swim in one of the clearest lakes in Ontario. Explore the lake on our kayaks, paddleboards and canoe. Bring your fishing gear for some excellent fishing. Savour cozy evenings around the firepit, creating lasting memories under starlit skies. Your lakeside getaway awaits!

Guest favourite
A cozy living area features a blue sofa and two wooden chairs, complemented by a small side table. Decorated with vintage skis mounted on the wall, soft lighting creates a warm environment. A door with a window provides access to the outdoors.
Apartment in Alexandria Bay
4.9 out of 5 average rating, 30 reviews

New downtown loft apartment #2

Newly renovated loft in the heart of downtown Alexandria Bay! Easy access to boat tours, shopping, restaurants, and all that the 1000 Islands has to offer! Located right next to Rotary Park and only steps from the Riverwalk and public gazebo. And Scenic View Park and the public beach are just down the street. The loft has everything you need for a comfortable stay. There is a grill and outdoor table for cookouts. There's even a record player and a collection of records to enjoy!

Top Guest favourite
A multi-story townhouse located along the waterfront features multiple balconies overlooking the St. Lawrence River. The building is flanked by other structures, and two boats are docked at the private pier, which is equipped with seating for relaxation.
Townhouse in Alexandria Bay
4.96 out of 5 average rating, 53 reviews

Downtown A-Bay getaway right on the St. Lawrence

If you are looking for a place to get away from reality, this is the place to stay! Located close to Downtown Alex Bay, right on the St. Lawrence River w/21ft of dock for your boat. Park your car and walk to the bars and restaurants. Not far from state parks and wineries. Our home has 2 balconies and a dock to hangout on. It comes with all the amenities you will need for your vacation! It is the end townhouse on the right side. Parking for 4 sedans and additional parking close.

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, 110 reviews

Honeybee Haven - Dog Friendly, Free Parking

Escape to a cozy, dog friendly haven, perfect for embracing the magic of the winter 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 winter getaway. Located minutes off of Hwy 401 and the US border crossing, an hour from both Kingston and Ottawa and two hours from Montreal.

Popular amenities for Cherry Island holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Jefferson County
  5. Alexandria
  6. Cherry Island