Vacation rentals in Waupoos Island

Waterfront Casa in wine County w/SAUNA and HOT TUB

Escape to this beautifully updated lakefront home on 170ft of private shoreline in beautiful Prince Edward County. Enjoy our new panoramic view sauna, hot tub and outdoor shower. This relaxing getaway is located on the Bay of Quinte, just 2hrs east of Toronto. A 30 min drive to Sandbanks, 20 mins to Picton/Wellington. Close to many wineries and breweries. Large yard space makes this an ideal home for groups, couples and families looking for postcard views and private spa amenities. ST-2023-0002

Stunning Prince Edward County Post & Beam Retreat

Welcome to Three Keys Waupoos, the County's ideal luxury accommodation for those who are looking for elegance, beauty, and comfort. This retreat is situated in the the heart of all things that make the County memorable; wineries, orchards, cheese factories, and scenic vistas. The house is all about open spaces and beautifully constructed post and beam craftsmanship. A short drive to many desirable County destinations, you'll be happy you chose our house overlooking Smith's Bay, Lake Ontario!

The Disco Garden Party by The Post Office Motel

Imagine arriving at a secluded mid-century modern retreat, where design and comfort both take first place. You sink into the warmth of your private hot tub, the sky above unfolding into a blanket of stars. Tonight, the Milky Way puts on a show just for you. Later, laughter fills the air as you gather around the fire pit, roasting gooey s’mores with family and friends. Located just minutes to secret speakeasy bars and wine lounges, wineries, the Mustang Drive-In and Sandbanks Provincial Park!

Waterfront Bunkie in PEC

Take it easy at this tranquil PEC getaway overlooking Smith's Bay. Located in Accommodating Bay campground, the spacious glamping bunkie features a king bed, fire pit, Keurig, and stunning waterfront views. While there’s no kitchen, the BBQ and fire pit make outdoor cooking part of the fun glamping experience. Enjoy a private washroom with shower next to the bunkie, and relax by the lake at the common swimming area just steps away. Pack up your glamping essentials and take the trip to PEC!

Escape Goat Hideaway at Barking Goat Farms

“Glamping” at its best. Come experience an off grid all season cabin, tucked away in a very private location at Barking Goat Farms, between Toronto and Ottawa. Enjoy your morning coffee on the lovely screened in porch and spend you evenings around the campfire star gazing amid the peaceful surroundings. Many local attractions to visit or just unplug and relax. Perfect for a couples romantic escape or a fun girls getaway. Enjoy a complimentary meet and greet with our goats and donkeys

From quiet rivers to starlit skies,

Experiencing forest bathing while you are also enjoying the comfort of our bubble, Escape the hustle of the modern lifestyle and re-balance your Self with the rythme of nature. Inside, there is a Queen-size bed and wood stove will keep you toasted. No running water; you will find an outhouse a few steps away from the dome. Cook outside on the BBQ, relax in the hamac and explore nature on our trail or in a kayaks or paddle board. A unique way to enhance your experience? Rent a sauna!

Little Ben Prince Edward County

Little Ben's license allows 2 adults and one child age 10 and under. Located 10 feet from Lake Ontario, in the heart of beautiful Wellington, Little Ben is a fully renovated 1 bedroom cottage in the centre of wine country. Little Ben offers a fully equipped kitchen, a dining area and a comfy living area with a wood stove. The true glory of Little Ben exists outside its walls--you are just a mere ten steps down to your own limestone beach on Lake Ontario! Licence # ST-2019-0358

The Falconer Carriage House

This unique place has a style all its own. The Falconer Carriage House is the latest restoration project by Alex Fida. This 1850's timber frame gem in the centre of Picton is a giant volume of space within walking distance of restaurants, bar, shops. Over 1400 square feet of pure inspiration. The carriage house has a 3 piece bathroom, 2 sleeping lofts (one king and one queen bed), kitchenette and generous living room. Enjoy 2 private outdoor patio spaces. License # 225-0006

Peaceful Peninsula. A Private Waterfront Oasis.

Please note summer 2026 (June 20-August 28) is weekly rentals Friday to Friday. Come and unwind on a private peninsula with water surrounding you on 3 sides. Peaceful peninsula is the perfect private, tranquil getaway. A place for mind, body and soul to find rest. NEW! CEDAR BARREL SAUNA with panoramic views, hot tub, seasonal outdoor shower, wood stove, 2 outdoor fire pits and a day bed in the gazebo all provide ample opportunities for relaxation. ST-2020-0226

The Prince Edward County Church, A Unique Escape

Stunning 1888 converted church in Prince Edward County on a private 2.3-acre waterfront property backing onto the Bay of Quinte. This one-of-a-kind stay blends soaring ceilings and historic charm with modern luxury. Sleeps 8 adults with 4 bedrooms, lake views, direct waterfront access, high-speed WiFi, Sonos, fireplaces, kayaks, and more. Featured in Forbes, House & Home & Cottage Life with over 300 guest reviews.

Parkway Lake House: Modern retreat w/ hot tub

Newly renovated along the shores of Lake Ontario, Parkway Lake House is the perfectly secluded modern retreat to step away from everyday life yet feel right at home. Gather around with friends and family and enjoy the laidback luxury. The Parkway Lake House was designed by Tiffany Leigh Design and featured on The Globe and Mail, Country Home and the Haven List! Photo credit: Patrick Biller and Christine Reid

Clover House - Pet Friendly w Hot Tub & Beach Pass

This open and airy vacation home boasts 4 bdrm/5 beds/2,800 sq ft for you to enjoy in the heart of PEC, just 5 mins from the adorable town of Picton. The 1.5 acre, private, east facing backyard is a stunning place to watch the sun rise with your morning coffee or sit with your favourite wine from any of the local vineyards in our hot tub. Perfect for big groups – and pet friendly! @thecloverhousepec