Photo by AMANDA

Wellesley Island holiday lettings

We found 226 holiday rentals — enter your dates for availability

Discover a selection of 19 homes and other holiday rentals in Wellesley Island that are perfect for your trip. Holiday rentals offer the best amenities for your family, friends or furry companion, such as Wi-Fi and a hot tub. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Wellesley Island

Showing deals for:19 Dec - 26 Dec

Image gallery for “GimmeShelter” Cozy 4 bedroom cottage in the heart of the Thousand Islands

Riverside Deck
9.6 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)

“GimmeShelter” Cozy 4 bedroom cottage in the heart of the Thousand Islands

Redwood, NY

8% off
Price is £1,750
for 7 nights, 1 cottage
£250 per night
includes taxes & fees
“GimmeShelter” Cozy 4 bedroom cottage in the heart of the Thousand Islands

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Wellesley Island

Find out more about Wellesley Island

Why people love visiting historical Wellesley Island

Enjoy the history and other features of Wellesley Island. Renowned for its island views, boating and riverfront, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Wellesley Island

Are you searching for things to do while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Wellesley Island a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Thousand Islands Winery (1.7 mi / 2.7 km)
  • Smuggler's Glen Golf Course (4.2 mi / 6.8 km)
  • Gananoque Boat Line (8.6 mi / 13.9 km)
  • Lil' River Fudge Co / 5&10 Variety Store (3.5 mi / 5.7 km)
  • The Landon Bay Centre (5.4 mi / 8.6 km)
  • Coyote Moon Vineyards (5.8 mi / 9.3 km)

Exploring the natural features in Wellesley Island

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Wellesley Island is a great place to get outside. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • St. Lawrence Islands National Park (2.9 mi / 4.6 km)
  • Scenic View Park (3.3 mi / 5.3 km)
  • Heart Island (3.6 mi / 5.7 km)
  • Thousand Islands National Park (3.8 mi / 6.2 km)
  • Confederation Park (9.1 mi / 14.6 km)
  • Black Lake (22.5 mi / 36.2 km)

How to get to and around Wellesley Island

Fly into Watertown, NY (ART-Watertown Intl.), the closest airport, located 22.3 mi (35.8 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Kingston, ON (YGK-Norman Rogers), which is 31.1 mi (50.1 km) away.

Frequently asked questions

What is the best area to stay in Wellesley Island when booking a holiday rental?
When considering a holiday rental on Wellesley Island, the area around the Thousand Islands State Park is an excellent choice. This picturesque location not only offers stunning views of the St. Lawrence River but also provides easy access to a variety of outdoor activities. The park is a fantastic spot for hiking, picnicking, and birdwatching, making it a haven for nature lovers.

Another appealing area is the vicinity of the Wellesley Island Marina. This lively spot is great for those looking to enjoy water activities such as boating and fishing. The marina area is often bustling with local charm and offers a few delightful eateries where you can savour fresh local seafood while enjoying the serene waterside atmosphere.
How much does it cost to rent a holiday home in Wellesley Island?
Prices for holiday rentals in Wellesley Island vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Wellesley Island to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Wellesley Island holiday house rentals?
You can find great discounts on house rentals in Wellesley Island on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Wellesley Island?
For renting a beach house in Wellesley Island, the Thousand Islands region offers delightful options along the picturesque shores of the St. Lawrence River. The area around Wellesley Island State Park is particularly appealing, where visitors can find charming cottages and homes that provide direct access to sandy beaches and scenic waterfront views. Many of these properties come equipped with amenities such as outdoor decks, BBQ facilities, and spacious living areas, making them ideal for families or groups looking to enjoy a relaxing retreat by the water.

Further north, the neighbourhoods near the Boldt Castle provide additional options, with a selection of waterfront homes featuring private docks and stunning views of the castle itself. These rentals often include modern conveniences such as fully equipped kitchens, Wi-Fi, and air conditioning, ensuring a comfortable stay. Guests can enjoy the nearby attractions, including boat tours to the castle and various recreational activities like kayaking and fishing.
What is the most popular type of holiday rental accomodation in Wellesley Island?
In Wellesley Island, holiday houses are the most popular type of rental, with around 17 available throughout the area. These houses offer spacious living arrangements, with multiple bedrooms, fully equipped kitchens, and often outdoor spaces for enjoying the scenic views of the St. Lawrence River. Many of these properties are situated in serene, natural settings, making them ideal for families or groups looking to unwind in a peaceful environment. Additionally, there are several cottages and cabins that provide a more rustic charm, featuring cosy interiors and close proximity to outdoor activities such as hiking and boating.
Are there any family house rentals in Wellesley Island?
In Wellesley Island, New York, there are a variety of family-friendly house rentals available, with around 19 options to choose from. This picturesque area is part of the Thousand Islands region, offering families a great blend of natural beauty and outdoor activities. Many of these properties feature spacious living areas, fully equipped kitchens for family meals, and outdoor decks or patios ideal for enjoying the lovely surroundings. Some homes even provide amenities such as private docks for boating adventures and access to nearby beaches, enhancing the overall experience for visitors.
Can I find long-stay holiday rentals in Wellesley Island?
A long-stay holiday rental in Wellesley Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Wellesley Island?
In Wellesley Island, there are several pet-friendly house rentals available, with around twelve properties to choose from. Many of these holiday rentals offer comfortable amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can roam freely. Travellers can expect features like fireplaces, private decks, and sometimes even access to waterfront views, enhancing the overall experience of their stay.
Are there any remote work holiday rentals in Wellesley Island?
In Wellesley Island, there are around 25 remote work holiday rentals available, making it a suitable destination for those looking to combine work and leisure. Many properties offer essential amenities such as Wi-Fi, dedicated desks, and comfortable office chairs, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Wellesley Island holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Wellesley Island with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Wellesley Island?
In Wellesley Island, popular holiday rental amenities include kitchens equipped with cookware, dishware, and utensils, allowing guests to prepare their own meals. Most rentals also feature microwaves and refrigerators, ensuring convenience for those who prefer a self-catering experience.
When is the best time to visit Wellesley Island for a holiday rental?
The best time to visit Wellesley Island for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant period attracts families and adventure seekers eager to enjoy the island's stunning natural beauty, particularly in the Thousand Islands region. Expect warm temperatures, typically in the mid to high 20s Celsius, which are great for outdoor activities such as kayaking, hiking, and swimming in the refreshing waters of the St. Lawrence River.

During this time, the island buzzes with life, as visitors partake in various water sports and explore the picturesque parks. The summer months also feature numerous events and festivals, enhancing the lively atmosphere and providing ample opportunities for socialising and entertainment.

For those looking for a more tranquil experience, consider visiting in November. While this is outside the peak season, the serene beauty of Wellesley Island during late autumn offers a unique charm. Cooler temperatures in the low single digits Celsius create a peaceful environment for leisurely walks and enjoying the scenic views without the summer crowds.
How early should I book a Wellesley Island holiday rental?
Book your Wellesley Island holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Wellesley Island home rental booking on Vrbo?
To find Wellesley Island holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Wellesley Island holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Holiday Rental options in Wellesley Island
Ski holiday rentals in Wellesley Island
Standard Link for Wellesley Island
Family-friendly holiday rentals in Wellesley Island
Standard Link for Wellesley Island
Holiday rentals with hot tub in Wellesley Island
Standard Link for Wellesley Island
Lake holiday rentals in Wellesley Island
Standard Link for Wellesley Island
Pet-friendly holiday rentals in Wellesley Island
Standard Link for Wellesley Island
Mountain holiday rentals in Wellesley Island
Standard Link for Wellesley Island
Beach holiday rentals in Wellesley Island
Standard Link for Wellesley Island
Holiday rentals with pool in Wellesley Island
Standard Link for Wellesley Island
Oceanfront holiday rentals in Wellesley Island
Standard Link for Wellesley Island
Monthly rentals in Wellesley Island
Standard Link for Wellesley Island

More Holiday Rentals ideas

Shelter Island Holiday Rentals
Standard Link for Shelter Island
Poughkeepsie Holiday Rentals
Standard Link for Poughkeepsie
Hunter Holiday Rentals
Standard Link for Hunter
Mamaroneck Holiday Rentals
Standard Link for Mamaroneck
Hampton Bays Holiday Rentals
Standard Link for Hampton Bays
Rye Holiday Rentals
Standard Link for Rye
Millport Holiday Rentals
Standard Link for Millport
Westhampton Beach Holiday Rentals
Standard Link for Westhampton Beach
Hastings-On-Hudson Holiday Rentals
Standard Link for Hastings-On-Hudson
Syracuse Holiday Rentals
Standard Link for Syracuse
Southampton Holiday Rentals
Standard Link for Southampton
Sag Harbor Holiday Rentals
Standard Link for Sag Harbor
Ellicottville Holiday Rentals
Standard Link for Ellicottville
White Plains Holiday Rentals
Standard Link for White Plains
New Rochelle Holiday Rentals
Standard Link for New Rochelle
Saratoga Springs Holiday Rentals
Standard Link for Saratoga Springs
Long Beach Holiday Rentals
Standard Link for Long Beach
Woodstock Holiday Rentals
Standard Link for Woodstock
Ithaca Holiday Rentals
Standard Link for Ithaca
Montauk Holiday Rentals
Standard Link for Montauk
Niagara Falls Holiday Rentals
Standard Link for Niagara Falls
Lake Placid Holiday Rentals
Standard Link for Lake Placid
Albany Holiday Rentals
Standard Link for Albany
Southold Holiday Rentals
Standard Link for Southold
Yonkers Holiday Rentals
Standard Link for Yonkers
East Hampton Holiday Rentals
Standard Link for East Hampton
Old Forge Holiday Rentals
Standard Link for Old Forge
Amagansett Holiday Rentals
Standard Link for Amagansett

People also search for

White Plains Apartments
Standard Link for White Plains
Yonkers Apartments
Standard Link for Yonkers