Owner Direct Vacation
Rentals in Wellesley Island
The Best Owner Direct Vacation Rentals in Wellesley Island. Explore thousands of vacation home rentals, large cabins, and villas near Wellesley Island
GUESTS
Explore the Best Wellesley Island Vacation Homes
Looking for the perfect place to stay in Wellesley Island? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Wellesley Island character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Wellesley Island Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Wellesley Island
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Popular Neighborhoods for Wellesley Island Vacation Rentals
What are the best areas to stay in Wellesley Island
Discover the top neighborhoods in Wellesley Island and choose a place that suits your stay.
Monday Feb 16
Wellesley Island, New York
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Wellesley Island vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Wellesley Island
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How to Reserve Your Wellesley Island Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Wellesley Island Vacation Rental FAQs
1. What are the top vacation rentals in Wellesley Island?
There are a lot of options in Wellesley Island. If you plan on staying in the Wellesley Island area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Wellesley Island:
- Beautiful waterfront cottage where you feel like you can touch the ships.
- Newly built cottage in historic Thousand Island Park, New York
- Nearley New Lakefront Cabin - Lake of The Isles
- Spacious, Relaxing, Simplified Living With The Best Screened Porch Of All!
- Tranquil, Secluded, Updated Two-Acre Wellesley Island Waterfront, Drive-To Home
- Ice fishing! YEAR ROUND Lake of the Isles Waterfront Cottage & boat dock!
- Spacious Peaceful home in the Woods on Wellesley Island
- Island Boathouse w/boatslip
- Private Home on Tranquil Island - Accessible Only by Boat
- Charming 2-bedroom cabin with AC, WiFi in wonderful Wellesley Island
2. Which vacation homes in Wellesley Island are best for families?
If you are looking for a family-friendly vacation home in Wellesley Island, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Wellesley Island:
3. How many vacation rentals are available in Wellesley Island?
Currently, the total number of properties listed in 2026 is over 75 in the Wellesley Island area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Wellesley Island.