Holiday rentals in Cherry Island

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Top-rated holiday rentals in Cherry Island

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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, 180 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

Guest favourite
An open concept living room features cathedral ceilings and ample natural light from floor-to-ceiling windows. A comfortable seating area includes a sectional sofa and a coffee table, while a large television is mounted on the wall. A staircase leads to an adjacent space.
Home in Wellesley Island
4.82 out of 5 average rating, 68 reviews

Outdoor Adventure Home: Golfing, Hiking & Kayaking

Escape to a 3-bed, 2-bath home on Wellesley Island with golf course views. Cathedral ceilings and an open concept living room/kitchen provide spacious living. Enjoy an attached 2-stall garage, private driveway, and golf cart. Miles of hiking trails start in the backyard. Relax on the back deck with grill. Perfect for families, golfers, and nature lovers, this luxury golf course retreat offers relaxation and outdoor activities. Book your stay now to enjoy a private retreat on Wellesley Island!

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

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.

Top guest favourite
A brown cottage is situated amidst greenery, featuring a wooden deck with seating areas. The yard is well-kept, showcasing a grassy space and two white lounge chairs. Nearby, ornamental plants and trees provide subtle shade, while a Canadian flag flutters gently in the breeze.
Cabin in Leeds and the Thousand Islands
5 out of 5 average rating, 19 reviews

Riverfront Year Round Cottage

Relax with the whole family at this peaceful place to stay. This beautiful 3 bedroom, 1 bath, (1 queen bed), (1 double bed), (1 twin bed) is located in the heart of the beautiful 1000 Islands. Located 5 minutes from the US border. This cottage/house has air conditioning/ furnace, wood stove, laundry, dishwasher, tv, wifi, propane bbq, coffee maker, toaster, microwave, stove-oven, refrigerator/freezer. A dock for your small boat or seadoo is also available. Canoe and life jackets provided.

Superhost
Cabin in Leeds and the Thousand Islands
4.88 out of 5 average rating, 131 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!

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.
Guest house in Chaumont
4.99 out of 5 average rating, 123 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
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.

Superhost
A white geodome is situated on a raised wooden deck, surrounded by lush green grass and trees near the water's edge. The calm surface of Varty Lake reflects the vibrant blue sky and the natural scenery.
Dome in Yarker
4.93 out of 5 average rating, 130 reviews

Sky Geo Dome on the Lake

Our beautiful geodome offers a unique glamping experience with breathtaking lake views. Perfect for romantic getaways, celebrations or family vacations. Enjoy stunning sunrises, stargaze, roast marshmallows by firepit, BBQ, play air hockey/pool/axe throwing, enjoy a night sky projector -indulge in peace & serenity. Varty Lake is ideal for fishing, kayaking & canoeing. Just 15 min from amenities & 30 min from alpaca farms, wineries, 1000 Islands, & stargazing in Stone Mills.

Guest favourite
The exterior of a historic home is shown, featuring a light gray facade, a new metal roof, and large windows. A welcoming enclosed porch is visible at the front, surrounded by lush greenery and landscaping. A paved path leads to the entrance.
Townhouse in Clayton
4.97 out of 5 average rating, 125 reviews

Heron House (Bay side) Riverfront/Docking/Ramp

The historic, circa 1880’s Heron House vacation home is balanced on the edge of the village of Clayton, nestled in the protected French Bay harbor with breathtaking sunset views. Meticulously appointed, lovingly restored to its former, distinctive grandeur, and available for rent year-round. A short walking distance to all the village has to offer. From unique boutiques, the world-class Antique Boat Museum, fitness facilities, and River Yoga.

Guest favourite
Home in Henderson
4.98 out of 5 average rating, 160 reviews

Lakefront Cottage with Hot Tub, Infrared sauna

Escape to a boutique lakefront cottage on Lake Ontario, designed for a relaxing retreat. This well designed space features a private hot tub with sunset views, new 2 person infrared sauna, direct lake access, and a cozy wood-burning fireplace. Enjoy luxurious details like an espresso/coffee bar and two king bedrooms. Perfect for couples or small groups seeking privacy, comfort, and connection in a refined, spa-like atmosphere.

Top guest favourite
Tiny home in Perth
4.92 out of 5 average rating, 345 reviews

Off-grid A-frame cabin

Welcome to “The Hemlock” cabin 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 in a peaceful, private setting, relax and unwind by the fire! We look forward to having you! (:

Popular amenities for Cherry Island holiday rentals

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