Vacation rentals in Cherry Island

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Top-rated vacation rentals in Cherry Island

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Top guest favorite

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

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

5.0 out of 5 average rating, 25 reviews

Top guest favorite

Home in Gananoque

NEW - Waterfront Island Retreat | Sauna | Firepit

You love getting away to a cottage by the water, but you also appreciate elegant interiors that feel like a high-end spa. Why choose when you can have it all in the same place? Come stay in this 3000 sq ft, newly built bungalow on Howe Island, where tranquility, contemporary elegance and the natural beauty of the Thousand Islands come together to create one extraordinary getaway. Use this home as your HQ as you explore the Thousand Islands or stay in for a luxurious, rejuvenating retreat.

5.0 out of 5 average rating, 28 reviews

Superhost

Home in Gananoque

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.

4.69 out of 5 average rating, 143 reviews

Top guest favorite

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

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!

5.0 out of 5 average rating, 30 reviews

Top guest favorite

Home in Alexandria Bay

Otter Bay House

Discover the Otter Bay House, your waterfront escape nestled in the heart of Alexandria Bay. With just a few steps separating you from the serene bay waters, this recently renovated two-bedroom, one-bathroom haven is thoughtfully designed with a fully stocked kitchen to cozy furnishings, we've left no stone unturned to ensure your stay is convenient and memorable. The Otter Bay House is just a short walk away from the charming shops and delectable dining options of downtown Alexandria Bay.

4.9 out of 5 average rating, 48 reviews

Top guest favorite

Home in Alexandria Bay

The Crossmon House by Swan Bay Adventures

Welcome to our charming home in the heart of the 1000 Islands! Built in 1860 and thoughtfully updated in 2020, this centrally located village gem blends original character with modern comfort. Just 2 blocks from downtown restaurants, bars, shops, and attractions—yet tucked on a quiet street with a private, secluded feel. Enjoy a spacious backyard perfect for family games, relaxation, and fun. Keyless smart lock entry, high-speed WiFi, and smart TVs included. Your 1000 Islands base awaits!

5.0 out of 5 average rating, 19 reviews

Guest favorite

A spacious living area is furnished with a rust-colored sofa and two blue ottomans. A tan armchair complements the seating arrangement. Kitchen amenities are visible in the background, with white cabinetry and an open layout. Framed artwork adds color to the neutral walls.

Apartment in Alexandria Bay

New downtown loft apartment #1

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 huge deck with a grill and table for cookouts. There's even a record player and a collection of records to enjoy!

4.81 out of 5 average rating, 42 reviews

Top guest favorite

The exterior of the home showcases a two-story structure with a light-colored siding and prominent windows. A large front deck features white railings, surrounded by a spacious lawn and mature trees, offering a serene atmosphere. Clear blue skies provide a bright backdrop.

Home in Alexandria Bay

Swan’s Nest

Swan’s Nest is nestled between the American narrows portion of the main channel of the St. Lawrence River and peaceful Swan Bay. This 4 bedroom/3 full bathroom home features a gorgeous floor-to-ceiling river stone gas fireplace as the focal point of the main floor, as well as a fully stocked kitchen and king master suite. Downstairs is a cozy sun room with a fireplace, and an Irish pub style bar room. To the rear, double decks overlook the wide lawn and waterfront access to Swan Bay.

4.96 out of 5 average rating, 101 reviews

Guest favorite

A spacious living area is illuminated by natural light from multiple large windows, showcasing views of the water. Comfortable sofas are arranged around a central coffee table, and a dining table for four is visible in the foreground. A ceiling fan and mounted television are also included.

Condo in Alexandria Bay

Riverview Townhouse IV in Downtown Alexandria Bay

Experience all the 1000 Islands has to offer in the heart of downtown Alexandria Bay. This second floor unit sits just off of the Saint Lawrence River and boasts breathtaking views of Boldt Castle on Heart Island. You and your guests will be right at home in this two bedroom, one bath unit with central air conditioning that comes fully stocked with rental essentials. Downtown shopping and dining are steps away and Alexandria Bay's beautiful River Walk begins just out the front door.

4.82 out of 5 average rating, 55 reviews

Top guest favorite

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

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.

4.97 out of 5 average rating, 61 reviews

Top guest favorite

A serene view of the cottage alongside a calm bay, framed by tall pine trees. The structure reflects softly in the water, showcasing a wrap-around deck. Surrounding the bay is a natural landscape, with patches of greenery and lily pads visible on the water's surface.

Cottage in Alexandria Bay

Waterfront Cottage in Alex Bay w/ Hot Tub & Dock!

Blue Heron Bay Cottage is a fully-renovated, year-round, smart home with 3 bedrooms and 2 full baths. Located directly on a quiet bay off of the St. Lawrence River, with 278 ft of water-frontage and only ~1 mile from downtown Alexandria Bay! The cottage comfortably sleeps 6-8 people, making it the perfect retreat for families, friends, and couples looking for a getaway that is quiet and private, yet close to all of the activities the Thousand Islands region has to offer!

5.0 out of 5 average rating, 47 reviews

Top guest favorite

The exterior of a modern single-story home is showcased, featuring a mix of dark siding and a stone accent. A welcoming porch with wooden beams is surrounded by landscaped flower beds, while lush greenery from the surrounding forest enhances the serene atmosphere.

Home in Leeds and the Thousand Islands

Thousand Island Oasis: Spa, Sauna, HT | Sleeps 10

The Thousand Islands Oasis is a tranquil retreat nestled on 1.16 acres of partially forested land, offering complete privacy in a serene natural setting. Surrounded by lush greenery, this hidden gem provides a perfect escape from the hustle and bustle of everyday life. The oasis is an ideal place to unwind and reconnect with nature, featuring peaceful seclusion and the soothing sounds of the surrounding forest.

4.98 out of 5 average rating, 96 reviews