Holiday rentals in Prince Edward Bay

4 season cabin in the woods -A romantic Riverboat!

You won’t forget this memorable experience! A 1974 River Boat has been lovingly transformed in to a whimsical all season cabin. Come for the fantasy then bask in the comfort and romance of it. Luxurious amenities include everything but the kitchen sink..literally! A perk to no running water is that I do your dishes at my place while you relax! The houseboat is tucked in to the trees and just across the road from a lakefront park. Plus...a Playshed full of seasonal outdoor equipment is included!

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 suite in a peaceful farm like setting

Brand new, spotless & well equipped private suite with crisp white sheets & towels, super comfortable queen bed & lounge chairs, large bathroom and a beautiful bar. Located 12 minutes east of Picton, minutes away from Lake on The Mountain, County Cider Company, Cressy Mustard , Waupoos Winery + Stellas Eatery. Borrow our tandem bicycle for a rice down the road to County Cider Company. Bedding, towels + extra pillows provided, plus a fully equipped kitchenette with essentials and board games.

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!

A Waterfront Cottage To Recharge Tired Souls

Looking to get away from it all and recharging your tired working selves? Our newly renovated peaceful 2 bedroom waterfront cottage in Milford, Ontario, is yours for however long you need - a weekend, a week or a month! It's a place where you can let your hair down, do nothing but gaze on the swans that come visiting, enjoy a bonfire and a stunning sunset to end your day. I invite you to look at the pictures with info below each one to see samples of places awaiting your visit to our County!

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

Peaceful Peninsula. A Private Waterfront Oasis.

Please note summer 2025 (June 27-August 29) 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.

Peaceful Country Studio Retreat

Our private studio is ideally situated in quiet, rural Prince Edward County near beaches, restaurants, wineries, art studios and all the villages of our beautiful island community. Great for cyclists, artist/writer's retreat, or a romantic getaway. You are staying at a Super Host place. Our super host status was temporarily removed because we were closed during the pandemic. Proof of vaccination is required. Thank you. Licence No. ST-2019-0356

The Dunes Air B&B

Location, location!!! This super cute cabin is only a 2 minute drive to The Sandbanks Provincial Park, or a 15 minute walk! Bike to the park in under 10 minutes. located in a bustling community with live music & mini golf across the road. This adorable cottage in the county has everything you need to make your county visit perfect. Picton is under 15 minutes away, making shopping trips, visits to breweries, wineries and restaurants a breeze!