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*

Island Mill Waterfall Retreat-Nov-April Night Free

Listing description *ALL INCLUDED* ( with seasonal variations) HotTub~4 Watercraft~Park Pass~Bikes~Outdoor Fire & Shower~Veggie Garden A one-of-a-kind experience awaits you in our 200 year old converted limestone mill. This eclectic space with a private entrance is nestled between two waterfalls on an island in the Salmon River. The beautifully appointed 525 sq ft suite is right on the edge of the river. Dine & relax on your private patio overlooking the waterfalls and the old one lane bridge.

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.

ZenDen Cabin By The Pond

This unique little eco friendly hobby farm has a vibe all its own. Close to many amenities yet secluded in middle of it all. Wild bird watching, fishing in the pond, long walks in the field to catch the sunset. Enjoy a bonfire or just chill with the view. You will be transported to a peaceful place. Bay of Quinte, Sandbanks, Scenic Caves, Wineries all for you to explore. 8 minutes drive to Shannonville motor sports park Fresh eggs from my hens when they're available Geodesic Dome Greenhouse.

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!

South Bay Lakehouse. 4 acres - Waterfront!

16 minutes south-east of Picton is the picturesque enclave of South Bay. Serene farmlands, vineyards and pristine waterfront make this a stunning part of the County. The home sits on 4 acres with 400 ft of waterfront. You'll be a short drive from everything you need but miles away from the hustle and bustle of city life. This place is great for couples, small families, nature enthusiasts or anyone looking for a peaceful spot with spectacular sunsets :) License # ST - 2020 - 0067

Picton Creekside Retreat

Prince Edward County, Picton ON. STA Lic# ST-2019-0028. Our tiny home (540 square feet) is totally yours, 1 bedroom, deck with tables and chairs, sunny west exposure. Industrial chic, bright, large lot, pet friendly, Wifi, full kitchen, living space, office area, smart TV and air conditioned. We supply a seasons Day use Pass to the Sandbanks Provincial park for you to book your day(s) at the beach. To guarantee entry, you can book your dates up to 5 days in advance.

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

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