Vacation rentals in Waupoos Island

Chalet On The Bay at Waupoos w/ Hot Tub

Relax and unwind at Chalet On The Bay in beautiful Waupoos. Located just 10 minutes from Picton the property is ideally situated as a hub for accessing all the County has to offer. A new home w/ hot tub that features cathedral ceilings, loft style master and all modern finishes with a rustic feel. A great space for family outings, wine touring or a getaway with friends. Please note we DO NOT have access to water off of our property and don't allow parties or pets. Home is on private road.

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

Modern Rustic Charm

Luxurious 1-bedroom basement apartment just 4 minutes from downtown Napanee and 800m from the hospital. A short drive to Prince Edward County, famous for its breweries, wineries and Sandbanks Provincial Park. Enjoy a private entrance with a cozy patio and BBQ in a quiet setting. Inside, relax with radiant floor heating, an electric fireplace and a fully stocked upgraded kitchen. Bright, spacious and beautifully designed with modern rustic charm, this cozy retreat is perfect for your stay.

Apartment in Prince Edward County

Escape to your perfect countryside retreat! Just 5 minutes from Picton and a short drive to local breweries, wineries, shops and beaches, this cozy suite blends relaxation with adventure. Start your day on the spacious deck, taking in peaceful views of open fields as you sip your morning coffee. Whether you’re visiting solo, as a couple, or with a small family, you’ll find a warm, welcoming space designed for comfort and calm. Kid-friendly and ideal for a refreshing rural getaway!

Desta, A perfect home base to explore the County.

A quaint, and private getaway for those looking to unwind and recharge all four seasons. Enjoy views of the Bay of Quinte from your deck while sitting by the fire table, the front deck or the living room. Conveniently located a short drive from downtown Picton, Sandbanks Provincial Park & surrounding wineries. Minutes away from Lake on the Mountain and it's delightful restaurants. You will find Desta conveniently located to take full advantage of all that Prince Edward County has

STEPS to Main St & Dining -FREE Sandbanks Pass #2

FREE ONSITE PARKING & SANDBANKS PASS! Ditch the car - you are steps from the County’s best. WALK: Under 5 minutes to Zest, City Revival, The Armoury, The Royal Hotel, Baccado, Becon Bike & Brew, The Acoustic Grill, and so many more. BEACHES: Includes a FREE 2026 Sandbanks Pass (a $21/day value). We send your pass # early so you can reserve 5 days in advance and save your spot! SUNSETS: The Harbour is just a 2-minute stroll away for sunsets and the best breakfast in town.

Cozy PEC Retreat • Peaceful Winter Escape

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

Cottontail Ridge Guesthouse / Prince Edward County

Welcome to our cozy guesthouse designed for two in wine country! Cottontail Ridge is a modern cabin set on a tucked away farm acreage in beautiful Prince Edward County. Enjoy stunning views from the picture windows & deck that overlook acres of old grazing fields. You may catch a glimpse of our namesake cottontail rabbits— or see turkeys, coyotes, fox & deer out back. On summer nights fireflies light up the fields and you’ll hear a serenade from crickets and frogs ;)

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

Glorious Sunsets, Wellers Bay Prince Edward County

STA Licence #ST-2019-0185 Beautiful, Cozy, winterized cottage. Lot: 200’ deep/75’ waterfront. Walk-out just steps to shoreline. Water: great for swimming, shallow with a gradual slope. Property has plenty of sunshine/shade, you decide. Cottage: fully equipped, running water with hot water on demand. Quiet neighbourhood, on dead-end road. Book your vacation at "Glorious Sunsets" you’ll be pleasantly surprised! LGBTQ friendly!

thecountycricket, Luxury loft near Picton

Licence No. ST-2019-0357 Welcome to our guest loft at "thecountycricket". I am so sorry but our space is not suitable for infants or children. Our property is 34 acres with 6 acres fenced. We are 10 minutes from Picton Main Street. The loft is 1,200 square foot open concept space with a full coffee station and a cooks kitchen. We live in a quiet street in the country close to town and vineyards, breweries and cider houses.