Vacation rentals in Waupoos Island

Modern School House *SPA GETAWAY*HOT TUB & SAUNA*

​Welcome to the Schoolhouse, an 1859 original school remodelled for your boutique vacation getaway. Located on Glenora Road just a few minute drive from the glorious downtown shops & restaurants of Picton Main St. The central location also acts as a great jumping off point to enjoy all the spectacular wineries, craft breweries, art galleries, beaches & trails that the County has become known for. *Please note we are a family getaway and not set up to host those looking for a party atmosphere*

Waupoos Island View Cottages - The Ethan

The cottage is fully equipped with a kitchenette, including fridge, countertop convection oven and microwave. The stove does not work. Dishes, pots and pans as well as utensils. We stock the cottage with basic towels, toilet paper, dish soap, hand soap and kitchen towels. Barbeque and picnic table for eating by the water. Bring your own beach chairs, beach towels & water shoes. Enjoy your personal dock for leisure, swimming, fishing.....etc End your evening with a fire at your own fire pit.

Modern & Charming Eh-Frame | 4-Season Chalet

Escape the everyday chaos and unwind in this romantic A-frame home. Nestled on 36 acres of forest and marshland, this charming getaway will fulfill any couple’s desire for a private weekend in the woods to indulge in a deep connection with each other and with nature. High loft ceilings, exposed beams, wood burning fireplace, a cozy loft bedroom, spacious shower for two, and sunken soaker bathtub create an intimate and pleasing ambiance for your carefree retreat. Hosts an abundance of wildlife.

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 Bloomfield Guest House

Are you looking for an awe-inspiring, peaceful, retreat-like setting for your visit to The County? Book this well-crafted private guest-house in charming Bloomfield, perfectly located between Wellington and Picton. The expansive farm-field view will instantly ground and settle your being. Every aspect of this luxury offering has been designed and built with integrity and care. We welcome you to embody a felt-sense of coming home. Follow us @thebloomfieldguesthouse Licence # ST-2022-0076

The Prince Edward County Church, A Unique Escape

Stunning 1800's converted church in Prince Edward County with modern amenities on huge property. This unique 4 bedroom massive space has been restored to give a modern feel with all the old unique charm. Sitting on 3 acres, this property backs on to the Bay of Quinte. Only 15 minutes from the closest vineyard, 20 minutes from Wellington & Bloomfield. Property includes Wifi, Netflix, PrimeTV, Sonos fresh linens/towels, coffee, laundry, firewood for wood burning and a gas fireplace & more!

Spectacular Waterfront Home in PEC

Situated on the edge of the beautiful Bay of Quinte, this brand new modern build is sure to steal your breath. Built in 2023, this stunning two-storey waterfront oasis, Water’s Edge, is located just over the Bay Bridge in spectacular Prince Edward County. Featuring two kayaks, fishing gear, outdoor propane fire table, and an upper and lower deck with front row seats to the most unforgettable sunsets. Water’s Edge is conveniently located to both Belleville and all that PEC has to offer.

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

Cozy PEC Retreat

Mya’s Place is designed for rest, quiet, and reset. In the winter and early spring, Prince Edward County becomes peaceful and uncrowded, perfect for couples, remote workers, creatives, and anyone needing space to slow down. Cozy interiors, calm energy, and everything you need for a true escape. Drive to downtown Picton or the beautiful Sandbanks Beach in under 30mins. A provincial parks pass has been provided for your convenience. STA #2024-0187 R1

Picton Bay Hideaway

Picton Bay Hideaway is a family owned and operated licensed waterfront bungalow with 2 bedrooms and a walk out basement that can comfortably sleep up to 4 adults plus 2 children. This getaway is ideal for those wanting to slow down, relax and spend quality time with loved ones or for those who are looking for a quiet and peaceful workspace retreat. Whether you are a wine, food, fishing, or a beach goer, there is something for everyone in Prince Edward County (PEC)!

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