Wellesley Island vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Wellesley Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Cottage in Clayton, New York, US

4.9 out of 5 average rating, 142 reviews

The Island Bay Waterfront Cottage

We welcome you to the Island Bay Cottage! Come enjoy your stay in our fully brand new remodeled waterfront cottage right outside the gorgeous town of 1000Islands Clayton NY! We’ve set up our wonderful place with all the creature comforts of home for our friends, family and guests to come in, plop down and feel right at Bay! Full kitchen with all essentials Huge living room (equipped with even a massage recliner!!) Free Wi-Fi, Fire smart TV, washer/dryer brand new A/C Large Patio area to relax!

Dec 15 – 22

G$31,619 GYD per night

Guest favorite

Bungalow in Alexandria Bay, New York, US

4.98 out of 5 average rating, 127 reviews

Cozy, private home in Alexandria Bay w/King Sz bed

TheA-Bay Bungalow@24 Margaret Ave is in The heart of the 1000 Islands.Walking distance to the beautiful St.Lawrence River and downtown Alex Bay.The A-Bay Bungalow is located in a quiet residential area.I am committed to creating an amazing guest experience&infusing great hospitality for everyone involved.The quaint&cozy home features hardwood floors,heat A/C and super easy self check in. It is the perfect get away.We also have room to park your boat/trailer& car.Walking distance to boat launch.

Feb 3 – 10

G$36,683 GYD per night

Guest favorite

Guest suite in Kingston, Canada

4.99 out of 5 average rating, 116 reviews

Cozy & Spacious Suite near CatCentre

Welcome to Kingston! Our basement apartment is now re-opening for 2024. For your ultimate comfort, we proudly offer: + A private entrance + A self check-in protocol + 2 queen beds + 1 full bathroom + 1 well-equipped kitchen + Laundry appliances + An experience with Alexa, our smart home assistant + Safe neighbourhood with parks and playgrounds nearby + Proximity to the mall, supermarkets, restaurants, and bus stations in walking distance + 5 mins to Highway 401 and 15 mins to Downtown by driving

Aug 9 – 16

G$18,364 GYD per night

Guest favorite

Cottage in Sydenham, Canada

4.97 out of 5 average rating, 122 reviews

Luxury on the Lake

Reconnect with nature at this unforgettable cottage escape. Perfect for families, couples, or anyone wanting to relax! Furnished with clean modern furniture. Beautiful, refreshing Sydenham Lake is steps from the cottage and the water is very deep off the dock so jump right in!! or fish, paddleboard, snorkel, paddle boat, canoe, whatever calls to you! Cottage is a 20 min walk to the town of Sydenham (which has a sandy public beach, boat launch, LCBO, Foodland, etc.) and 20 min drive to Kingston.

Oct 23 – 30

G$36,694 GYD per night

Guest favorite

Apartment in Redwood, New York, US

4.92 out of 5 average rating, 147 reviews

A Simple Roof

THIS IS NOT A VACATION HOME. Self-check-in/check-out. Old-fashioned, rustic apartment, painted wood floors, full kitchen, mud room, screened porch; boat/ATV parking; tent space. Ready for year-round outdoor sports, fishing, boating, biking, family camping trips. Near 1000 Islands, several lakes/waterways, 5 room apartment is one side of host duplex, 3 private entrances. King bed, 1 twin upstairs, 2 folding cots. Bathroom downstairs. WIFI; FireTV, HDMI cord provided; TVs w/DVD. RED box nearby.

Dec 25 – Jan 1

G$17,499 GYD per night

Guest favorite

Cottage in Battersea, Canada

4.85 out of 5 average rating, 151 reviews

Sweet Cottage Surrounded by Nature Near Kingston

Welcome to our cottage on Dog Lake, a beautiful and serene lake noted for its fishing, paddling and wild life. Nestled between Toronto and Montreal, we are the perfect destination for those needing some quiet time while visiting the 1000 islands. Build a bonfire, go for a swim, explore your surroundings by canoe or on foot. There's lots to do. Or, do nothing at all. Enjoy a cup of coffee on the screened in porch while listening to loons watching hummingbirds and fireflies. And breathe!

Dec 6 – 13

G$22,149 GYD per night

Guest favorite

Apartment in Chaumont, New York, US

4.96 out of 5 average rating, 249 reviews

The perfect 1000 Island Nature Get Away!

Dante's Den is located in Upstate New York's Thousand Island region and sits directly on the Chaumont River. Our suite has a private entrance, a river facing patio, a cozy bedroom and a spacious living room and new fully functional kitchen. Dante's Den is a great spot for people who enjoy the outdoors and like to be active. Great cycling routes, walking trails, public boat launches, beaches and parks are near by. Alexandria Bay, Cape Vincent, Clayton, and Watertown are also close.

Dec 10 – 17

G$22,644 GYD per night

Guest favorite

Cottage in Leeds and the Thousand Islands, Canada

4.93 out of 5 average rating, 188 reviews

Smugglers Getaway on the St. Lawrence River

Enjoy your privacy in this Riverfront cabin in the historic Smugglers Cove on the St. Lawrence River in the heart of the 1000 Islands. You'll enjoy 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.

May 6 – 13

G$38,080 GYD per night

Guest favorite

Cabin in Battersea, Canada

4.86 out of 5 average rating, 146 reviews

The Hideaway: Private waterfront getaway

Looking for a therapeutic retreat? Clear your mind as you breathe in the clean air and watch the swans swim by. Cozy, newly renovated cabin with loft on Milburn Bay which leads to the Rideau. Canoe, life jackets, wood stove, electricity, AC,BBQ, WIFI and parking for one vehicle. Three occupants only, number to be confirmed when booking. Bring your own drinking water, bedding, pillows and slippers. New indoor composting toilet. Please read entire listing. No pets, please.

Oct 12 – 19

G$16,918 GYD per night

Guest favorite

Cottage in Leeds and the Thousand Islands, Canada

4.97 out of 5 average rating, 285 reviews

Lyncreek Cottage

Lyncreek Cottage is open year round. it sits on private property on Lyndhurst river in Lyndhurst, Ontario. Observe various types of waterfowl or enjoy the sound of our meandering river as it flows into Lyndhurst Lake. This is all part of the natural surroundings in your own private cottage. A great place to stay if you are travelling through the area or while enjoying all the area has to offer including excellent fishing, paddling and hiking area trails.

Mar 18 – 25

G$15,277 GYD per night

Guest favorite

Guest suite in Gananoque, Canada

4.93 out of 5 average rating, 131 reviews

Sheri's Place

Your home away from home is a short drive from downtown Gananoque situated on a 6 acre private property. We are approx. 5 minutes from Downtown Gananoque and 25 minutes from Downtown Kingston. Private entrance to ensure personal private space. Our space is not designed for more than 2 guests. Please Note: We have had a name change to match our reviews we were Country Retreat, now we are 'Sheri's Place' welcome to your home away from home.

Dec 2 – 9

G$18,756 GYD per night

Guest favorite

Cabin in Seeley's Bay, Canada

4.91 out of 5 average rating, 179 reviews

Procrastination Bay Cottage

Peaceful setting on Stafford Bay. Great for fishing, canoeing, kayaking or just relaxing in the hammock. You can explore the Rideau Canal from Jones Falls to Upper Brewers without locking through. We have 2 canoes a paddleboat and 2 sit on top Kayaks ( one is a 2 seater) which you are welcome to use. You can launch your boat from the Main docks at Seeley's Bay or rent one from 2 local marinas.

Sep 26 – Oct 3

G$25,740 GYD per night