Holiday 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*

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!

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!

The Granary Flat - Lakeside, Historic Stone Mill

The Granary Flat is located inside of a historic stone mill on the shoreline of Bay of Quinte. With exposed beams and stone walls, this unique space has a lot of character and a rustic feel. Watch the Glenora Ferry pass by throughout the day and the activity at the Fishery building next door, or take a walk up to Lake on the Mountain Provincial Park where you can enjoy more breathtaking water views. This is a one of a kind and truly unique location that you simply must experience.

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

Southside Retreat in Waupoos: Waterfront&Wineries

This adorable 2 bedroom bungalow is located in the hamlet of Waupoos and is within walking distance to a winery, restaurants and cider company! A short walk down a grassy field takes you to our private waterfront with a sandy and rocky shore and with chairs for your own little slice of county heaven. 15 min. to the heart of Picton! *We are a fully licensed and legally operating Short Term Accommodator in the Municipality of Prince Edward County. License #STA-2019-0035

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