Vacation rentals in Waupoos Island

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Top-rated vacation rentals in Waupoos Island

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Guest favorite
A large window frames a serene view of Smith's Bay, revealing calm waters and a distant tree line. In the foreground, a vase of white orchids adds a touch of nature to the indoor setting, while a grassy area leads to the water's edge.
Cabin in Prince Edward
4.85 out of 5 average rating, 123 reviews

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.

Top guest favorite
The interior features a warm wooden aesthetic with high cathedral ceilings supported by exposed beams. A staircase leads to an upper level. The chef's kitchen includes a tiled countertop with a vase of flowers, while the dining area is visible in the background.
Home in Prince Edward
4.94 out of 5 average rating, 280 reviews

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!

Top guest favorite
A private hot tub is visible, featuring softly illuminated water. Nearby, a fire pit flickers gently, surrounded by greenery and string lights. The area offers modern outdoor seating and a serene atmosphere, enhancing the retreat's inviting space.
Guest suite in Prince Edward
4.95 out of 5 average rating, 107 reviews

The Disco Garden Party by The Post Office Motel

Imagine arriving at a secluded mid-century modern retreat, where design and comfort both take first place. You sink into the warmth of your private hot tub, the sky above unfolding into a blanket of stars. Tonight, the Milky Way puts on a show just for you. Later, laughter fills the air as you gather around the fire pit, roasting gooey s’mores with family and friends. Located just minutes to secret speakeasy bars and wine lounges, wineries, the Mustang Drive-In and Sandbanks Provincial Park!

Top guest favorite
A modern two-storey home features a sleek design with large glass windows and balconies. The outdoor area includes a spacious deck with seating arrangements, while a decorative neon sign reads 'Water's Edge' against a textured green wall, enhancing the contemporary aesthetic.
Home in Belleville
4.95 out of 5 average rating, 217 reviews

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.

Top guest favorite
A modern kitchen showcases light cabinetry and a spacious island with a wood storage area. Stylish light fixtures hang above, complementing colorful artwork on the walls. A dining area with wooden chairs is visible in the background, enhancing the room's inviting atmosphere.
Guest suite in Prince Edward
4.94 out of 5 average rating, 118 reviews

Stylish and Spacious Rental in Waupoos.

License number : ST-2022-0088 - 2 adults and 1 child under 10 This bright and spacious rental is the perfect place to spend your time in the county. Modern, stylish and filled with warm vintage accents, we have thought of everything you would need for a week or weekend away. Situated on a budding lavender farm in Waupoos this rental is a 5 minutes drive from the County Cider Company, 20 minute to Picton and 30 minutes to Sandbanks National Park. MAT is included in the nightly rate

Top guest favorite
An evening view of the cabin's entrance is lit by soft outdoor lighting. A welcoming porch features a wooden railing and decorative elements, while plants surround the steps. The structure has large glass windows, allowing a glimpse of the interior ambiance.
Farm stay in Newburgh
5 out of 5 average rating, 125 reviews

Escape Goat Hideaway at Barking Goat Farms

“Glamping” at its best. Come experience an off grid all season cabin, tucked away in a very private location at Barking Goat Farms, between Toronto and Ottawa. Enjoy your morning coffee on the lovely screened in porch and spend you evenings around the campfire star gazing amid the peaceful surroundings. Many local attractions to visit or just unplug and relax. Perfect for a couples romantic escape or a fun girls getaway. Enjoy a complimentary meet and greet with our goats and donkeys

Guest favorite
Dome in Plainfield
4.81 out of 5 average rating, 192 reviews

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!

Guest favorite
A scenic view of Adolphus Reach is captured from the cabin's vantage point, showcasing calm waters and a passing boat. Surrounding trees display autumn colors, contributing to the natural beauty of the landscape under a mix of blue and cloudy skies.
Guesthouse in Prince Edward
4.86 out of 5 average rating, 314 reviews

The Edge. Stunning view. EV Friendly

This private cabin and deck has a stunning view of Adolphus Reach from the top of a 200' escarpment. The property is located immediately east of Lake on the Mountain Provincial Park. Have a look on Google Maps. Day use at Sandbanks must be reserved. Text me for details of how I can reserve for you using my seasonal park pass saving you the $21 park fee. I'm required to charge HST if you choose to book via Airbnb but not otherwise. Posted price includes HST. ST-2019-0310

Top guest favorite
A spacious sleeping area includes a comfortable queen bed adorned with crisp white linens and decorative pillows. A cozy armchair is positioned nearby, complemented by a colorful area rug. Natural light filters through a small window, enhancing the bright and clean atmosphere.
Guest suite in Prince Edward
4.94 out of 5 average rating, 157 reviews

Modern suite in a peaceful farm like setting

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. A short bike ride down the road to County Cider Company. Bedding, towels + extra pillows provided, plus a fully equipped kitchenette with high quality essentials and board games.

Top guest favorite
A spacious deck features a seating arrangement of white chairs and a round table beneath a bright red umbrella. The view showcases rolling green fields leading towards a serene waterfront, framed by trees under a clear blue sky.
Bungalow in Prince Edward
4.99 out of 5 average rating, 125 reviews

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

Top guest favorite
A spacious deck features red Adirondack chairs positioned for lake views, overlooking calm waters at sunset. The horizon captures warm tones, while the reflection on the water creates a serene ambiance. Clear railing allows uninterrupted sightlines of the scenic surroundings.
Cottage in Prince Edward
4.95 out of 5 average rating, 187 reviews

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)!

Top guest favorite
An outdoor seating area is framed by large glass doors, revealing a serene water view. Comfortable seating is arranged around a central table on a patterned rug, creating a perfect spot for relaxation while taking in the sights of the bay.
Cottage in Prince Edward
4.99 out of 5 average rating, 178 reviews

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

Popular amenities for Waupoos Island vacation rentals

  1. Airbnb
  2. Canada
  3. Ontario
  4. Prince Edward County
  5. Prince Edward
  6. Waupoos Island