Wellesley Island vacation rentals

We found 223 vacation rentals — enter your dates for availability

Discover a selection of 20 homes and other vacation rentals in Wellesley Island that are perfect for your trip. Vacation rentals offer the amenities you expect for you and your friends, family, or even pets, like air conditioning and WiFi. You'll be able to choose a rental that has what everyone needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Wellesley Island

Why visit Wellesley Island

  • Stunning Natural Beauty: Wellesley Island boasts breathtaking views of the Thousand Islands and lush wilderness, perfect for outdoor enthusiasts.
  • Wellesley Island State Park: Explore this expansive park, which offers hiking trails, sandy beaches, and picnic areas amid scenic surroundings.
  • Charming Town of Orleans: Discover local history and friendly vibes in this quaint town, ideal for leisurely strolls and exploration.
  • Diverse Accommodations: Choose from a variety of vacation rentals, including cozy cottages and lakeside homes, to suit your getaway needs.
  • Outdoor Adventures: Engage in activities like kayaking, fishing, and hiking, making for an exciting and memorable vacation experience.

Popular types of accommodation in Wellesley Island

Discover the charm of Wellesley Island with a variety of vacation rentals to suit your needs. From houses and cozy cottages to modern apartments, there’s something for everyone. Whether you’re looking for a lakeside getaway, the best cabins, or a waterfront bunky, you'll find the perfect spot to relax and unwind. Explore our selection and make your next trip to Wellesley Island unforgettable.

  • Houses: The top choice for visitors to Wellesley Island, offering spacious and comfortable lodging perfect for families, friends, or couples.
  • Cottages: A charming option that provides a cozy, rustic retreat ideal for those seeking a peaceful getaway.
  • Apartments: A convenient choice for travelers looking for a home-like atmosphere with essential amenities.
  • Condos: A popular selection that combines comfort with community amenities for a relaxed stay.
  • Chalets: These inviting accommodations offer a unique blend of rustic charm and modern comforts, perfect for nature enthusiasts.**

Top attractions in and around Wellesley Island

Wellesley Island, New York, is a perfect destination for outdoor enthusiasts and couples seeking scenic beauty. Visitors can explore the stunning Wellesley Island State Park, enjoy the breathtaking views of the Thousand Islands, and discover charming local attractions. Whether you're looking for adventure or a romantic getaway, Wellesley Island offers a delightful mix of nature and exploration, making it an ideal spot for your vacation.

  • Thousand Islands Bridge: A modern marvel, this bridge connects Wellesley Island with the surrounding areas, offering stunning views and a vibrant atmosphere. It's a great spot for a leisurely stroll or a scenic drive.
  • Boldt Castle: Located 4 miles away, this enchanting castle exudes culture and romance. Explore its beautiful architecture and lush gardens, perfect for a memorable day trip.
  • Heart Island: Also 4 miles away, this picturesque island boasts outdoor activities and serene beaches, making it an ideal spot for relaxation and exploration.

Things to do recommended for couples

For a romantic getaway in Wellesley Island, enjoy a sunset picnic by the St. Lawrence River or explore the scenic hiking trails together. Don't miss a boat tour to admire the Thousand Islands—we guarantee it will be a memorable experience for you both.

Things to do recommended for families

Your family will love exploring the beautiful Wellesley Island State Park, where you can hike scenic trails and enjoy picnics. Kids will delight in swimming at the beach and discovering the area's rich wildlife. Don’t miss a boat tour of the Thousand Islands for breathtaking views.

Things to do recommended for groups

Explore the scenic beauty of Wellesley Island State Park with hiking trails perfect for group adventures, or enjoy a fun-filled day of kayaking on the St. Lawrence River. Don't miss a visit to Boldt Castle for a taste of local history and stunning architecture.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Wellesley Island

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your preferences in your search. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Wellesley Island with a group: Think about how many bedrooms you require, along with additional features like a full kitchen or outdoor space for group gatherings. Fortunately, you can easily apply filters for all these options and more on Vrbo.
  • Traveling to Wellesley Island with young kids: Traveling with young kids can be demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Wellesley Island: For many families, a vacation isn’t truly fulfilling without their beloved pet by their side. If you relate to this, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wellesley Island: If you're in search of vacation rentals offering discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Wellesley Island

Wellesley Island offers a perfect blend of natural beauty and adventure for tourists. Explore its stunning wilderness sites, relax on sandy beaches, and discover numerous nearby islands. Don't miss the charming Town of Orleans, where historical vibes meet friendly locals. Whether you're seeking a romantic getaway or exciting excursions, Wellesley Island and its surroundings promise an unforgettable vacation experience filled with scenic views and outdoor activities.

  • Alexandria Bay: Located just 3 miles from Wellesley Island, Alexandria Bay is a charming city renowned for its stunning outdoor scenery and romantic ambiance. Visitors can explore the picturesque waterfront, shop at local stores, and enjoy recreational areas perfect for relaxation and adventure. Key attractions include the breathtaking views of the lake and the iconic Boldt Castle, a magnificent structure that draws tourists for its history and architectural beauty. With various events and conferences held nearby, Alexandria Bay is a vibrant hub for both leisure and culture.
  • Clayton: Situated 7 miles from Wellesley Island, Clayton is a delightful city that beckons travelers with its outdoor beauty and romantic settings. This charming destination offers a variety of shopping experiences and recreational areas that cater to all ages. The nearby Thousand Islands National Park provides ample opportunities for hiking, kayaking, and wildlife watching, making it a perfect spot for nature lovers. Visitors can also enjoy the stunning views of the lake, which serve as a backdrop for many local events and gatherings throughout the year.
  • Thousand Island Park: Just 3 miles away from Wellesley Island, Thousand Island Park is a quaint village that offers a serene escape into nature. With its beautiful outdoor spaces and scenic views, it’s an ideal spot for those seeking romance and tranquility. The village features recreational areas, charming shops, and local stores, giving visitors a taste of the community's warm hospitality. Close by, the national state park and the pristine lake provide plenty of activities, including hiking and boating, making it a perfect destination for outdoor enthusiasts.

Best time to go to Wellesley Island

If you're planning a trip to Wellesley Island, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January21.2°F (-6.0°C)Light RainMostly CloudyLowSlightly Low
February22.3°F (-5.4°C)Light RainMostly CloudyAverageAverage
March31.1°F (-0.5°C)Light RainMostly CloudyAverageSlightly Low
April42.8°F (6.0°C)Light RainMostly CloudyAverageAverage
May55.2°F (12.9°C)Light RainMostly SunnyAverageAverage
June63.5°F (17.5°C)Light RainMostly SunnyHighSlightly High
July70.0°F (21.1°C)Light RainMostly SunnyHighSlightly High
August68.9°F (20.5°C)Light RainMostly SunnyHighSlightly High
September62.2°F (16.8°C)Light RainMostly SunnyAverageAverage
October51.1°F (10.6°C)Light RainMostly CloudyAverageAverage
November39.0°F (3.9°C)Light RainMostly CloudyLowAverage
December29.7°F (-1.3°C)Light RainMostly CloudyLowSlightly Low

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay can lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you find the best options for your travel plans.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers an easy-to-use platform for planning your travels. You can create new trips, continue from where you last left off, or organize your existing plans all in one place. Your saved or booked properties will be neatly categorized into Potential, Upcoming, or Current Trips for your convenience. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Why people love visiting historic 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 hoping to find things to do in the area? Venture out of your vacation home and check out everything that makes Wellesley Island a fun spot to vacation. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

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

Exploring the natural features in Wellesley Island

Whether you're an active traveler or just want to take in the scenery, Wellesley Island is a great place to spend some time outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Black Lake (22.5 mi / 36.2 km)
  • Grenell Island (3.8 mi / 6.1 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 center. If you can't find a flight that works for your travel itinerary, you could 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, New York, United States of America when booking a vacation rental?
When considering a vacation rental in Wellesley Island, New York, the most appealing area to stay is near the Thousand Islands region. This picturesque locale is renowned for its stunning natural beauty and a variety of outdoor activities. You can find numerous properties available, ranging from cozy cottages to spacious waterfront homes, making it easy to find something that suits your needs.

One of the top attractions in this area is the Thousand Islands National Park, where visitors can explore lush trails, go kayaking, or simply enjoy the serene views of the St. Lawrence River. Additionally, the nearby Boldt Castle, located on Heart Island, offers a fascinating glimpse into the area's history and architecture, making it a must-visit for anyone staying on the island.
How much does it cost to rent a vacation home in Wellesley Island?
Prices for vacation 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 vacation 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, travelers should consider the picturesque waterfront areas along the St. Lawrence River. The region features a variety of vacation rentals, many of which are situated near the scenic Wellesley Island State Park, known for its beautiful beaches and natural surroundings. Properties in this area often come with amenities such as private docks, outdoor seating areas, and access to kayaks or canoes, making them ideal for water enthusiasts looking to explore the river.

The nearby Thousand Islands region offers additional options, where visitors can find charming cottages and larger homes with stunning views of the water. Many of these rentals include features like fire pits for evening gatherings, spacious decks, and fully equipped kitchens, suiting families and groups seeking a relaxing getaway. The proximity to local attractions, such as the Boldt Castle and the Thousand Islands Bridge, enhances the experience for those looking to explore the area's rich history and natural beauty.

For those interested in outdoor activities, Wellesley Island provides access to hiking trails and opportunities for fishing, with many rentals conveniently located near these recreational spots.
Where are the best Wellesley Island ski resort rentals?
For skiing near Wellesley Island, travelers can explore options in the nearby area of the Thousand Islands region. While Wellesley Island itself is primarily known for its natural beauty and recreational opportunities, the closest ski resorts are located a bit further afield. The town of Alexandria Bay, just a short drive away, offers convenient access to winter sports facilities. Here, visitors can find cozy cabins and lodges that typically feature amenities such as fireplaces, kitchen facilities, and outdoor spaces for enjoying the scenic views.

Additionally, the nearby area around Lake Ontario, particularly in places like Sackets Harbor and Watertown, may provide further rental options. Many properties in these towns come with modern amenities, including Wi-Fi, heating, and comfortable living spaces, ideal for relaxing after a day on the slopes. Visitors can also enjoy local dining and entertainment options within a short drive, enhancing their overall experience.
What is the most popular type of vacation rental accomodation in Wellesley Island?
In Wellesley Island, vacation houses are the most popular rental option, with about 15 available across the island. These houses typically feature spacious layouts, multiple bedrooms, and amenities such as fully equipped kitchens and outdoor seating areas, making them ideal for families or groups seeking a comfortable retreat. Additionally, there are several cottages and cabins, which provide a cozy, rustic charm and often include features like fireplaces and proximity to nature for outdoor activities.
Are there any family house rentals in Wellesley Island?
In Wellesley Island, there are 19 family-friendly house rentals available, offering a wonderful opportunity for families to enjoy their time together. This area is known for its stunning natural beauty, with easy access to the Thousand Islands region, where outdoor activities abound. Many of these homes provide spacious living areas, fully equipped kitchens for preparing meals, and outdoor decks or patios great for relaxation.

Visitors will also find amenities like Wi-Fi and laundry facilities, which add convenience to their stay. Families can explore nearby attractions, including state parks with hiking trails, picnic spots, and access to the St. Lawrence River for boating and fishing.
Can I find long-stay vacation rentals in Wellesley Island?
A long-stay vacation rental in Wellesley Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Wellesley Island?
In Wellesley Island, there are several pet-friendly house rentals available, with around twelve options for travelers seeking accommodations that welcome furry friends. Many of these vacation rentals are situated near the scenic Thousand Islands region, providing access to beautiful waterfront views and outdoor activities.

Travelers can expect amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces like decks or patios, superb for enjoying the tranquil surroundings. Additionally, some properties may offer features like private docks, making it easy to explore the nearby waterways.

While enjoying your stay, you can take advantage of the local parks and natural areas, which provide opportunities for walks and outdoor adventures with pets, ensuring a pleasant experience for both you and your four-legged companions.
Are there any remote work vacation rentals in Wellesley Island?
In Wellesley Island, there are several options for remote work vacation rentals, with around 26 properties available that cater to the needs of remote workers. These rentals often feature essential amenities such as high-speed Wi-Fi, dedicated workspaces or desks, and access to printers, ensuring that guests can stay productive during their stay.

Many properties are situated near the scenic Thousand Islands region, offering a peaceful environment conducive to work while also allowing for relaxation and exploration during downtime. Expect to find amenities like comfortable living areas, fully equipped kitchens for home-cooked meals, and outdoor spaces to enjoy the beautiful natural surroundings. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Wellesley Island vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Wellesley Island with parking available—perfect for families or travelers 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, vacation rentals typically offer a range of popular amenities that enhance the guest experience. Most properties come equipped with a kitchen, allowing travelers to prepare their own meals and enjoy home-cooked dining. Many rentals also feature a deck or patio, providing an outdoor space for relaxation and enjoying the scenic surroundings. Onsite parking is commonly available, making it convenient for guests traveling by car. Additionally, properties often include coffee and tea makers for a cozy morning routine, and many have fireplaces, creating a warm and inviting atmosphere, especially during cooler months.
When is the best time to visit Wellesley Island for a vacation rental?
The peak travel season in Wellesley Island spans from June to August, making it the most popular time for vacation rentals as visitors flock to enjoy the beautiful summer weather. With warm temperatures typically ranging from the mid-70s to the low 80s Fahrenheit, this season is great for outdoor adventures like boating, fishing, and hiking in the stunning Thousand Islands region.

July stands out as the highlight of the summer, with vibrant activities and events that cater to families and outdoor enthusiasts alike. This month offers a lively option, allowing travelers to immerse themselves in local festivities, enjoy the scenic beauty of the St. Lawrence River, and take advantage of various recreational opportunities.

For those seeking a more budget-friendly experience, consider planning your visit in November. This quieter month provides a unique opportunity to explore the island's natural beauty without the summer crowds. Although temperatures start to dip, the tranquility of Wellesley Island in the fall offers a peaceful retreat, great for enjoying scenic walks and the crisp autumn air.

Ultimately, the best time to visit Wellesley Island depends on whether you prefer the vibrant excitement of the summer season or the serene charm of the quieter fall months.
How early should I book a Wellesley Island vacation rental?
Book your Wellesley Island vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Wellesley Island, New York, United States of America?
In Wellesley Island, visitors can explore the stunning natural beauty of the Thousand Islands region. One of the main attractions is the scenic Wellesley Island State Park, which offers hiking trails, picnic areas, and access to the St. Lawrence River for kayaking and fishing. The park is a great spot for outdoor enthusiasts, featuring diverse wildlife and picturesque views.

For those interested in history, the nearby Boldt Castle on Heart Island is a must-see, showcasing a grand early 20th-century mansion accessible by boat. The charming community of Alexandria Bay is also close by, where travelers can enjoy local shops, dining options, and boat tours of the surrounding islands.

Additionally, visitors can take advantage of the area's recreational activities, including golfing at the Wellesley Island Golf Course or exploring the scenic beauty along the riverfront.
Can I change or cancel my Wellesley Island home rental booking on Vrbo?
To find Wellesley Island vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Wellesley Island vacation 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More Vacation Ideas