Vacation rentals in Waupoos Island

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Waupoos Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Superhost

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

4.84 out of 5 average rating, 121 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

An A-frame house is presented with a blue exterior amidst a snowy landscape. The structure showcases a sloped roof with multiple windows and a door leading to a deck. Surrounding trees, partially covered in snow, create a serene and natural setting.

Home in HUNT

4.97 out of 5 average rating, 184 reviews

Modern & Charming Eh-Frame | 4-Season Chalet

Escape the everyday chaos and unwind in this romantic A-frame home. Nestled on 36 acres of forest and marshland, this charming getaway will fulfill any couple’s desire for a private weekend in the woods to indulge in a deep connection with each other and with nature. High loft ceilings, exposed beams, wood burning fireplace, a cozy loft bedroom, spacious shower for two, and sunken soaker bathtub create an intimate and pleasing ambiance for your carefree retreat. Hosts an abundance of wildlife.

Top guest favorite

A serene outdoor space features two large flower pots filled with vibrant pink and yellow blooms. A weathered wooden bench offers a resting spot amidst a backdrop of neatly trimmed evergreen trees and a paved stone area, creating a peaceful garden retreat.

Guest suite in Prince Edward

4.99 out of 5 average rating, 329 reviews

Rockery Suite - Picton 4 min to Main St ParkPass

Our spacious & welcoming Rockery Suite (licensed) - an inviting, fully equipped apartment with private entrance. Located less than 5 minutes from downtown Picton, the harbour, fine & casual dining, cafes, pubs, breweries, galleries & studios, shopping & so much more. Or take a short scenic drive to local wineries, beaches, ski & walking trails, Sandbanks Park, Lake On The Mountain, Glenora Ferry, Bloomfield, Wellington. Endless year round possibilities. Come and explore Prince Edward County.

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, 251 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

Bungalow in Prince Edward

4.92 out of 5 average rating, 424 reviews

Bright & Cozy Bungalow Close to Downtown Picton

This bright & cozy cottage-style bungalow is the perfect home base for your PEC getaway! It is centrally located in the heart of Picton, offering 1 bedroom, 1 bath, office area, deck with BBQ & small yard. Comfortably accommodates two adults. Short 5 min walk to downtown, where you can enjoy The Royal Hotel, boutiques, restaurants, cafe's, galleries & more. A short drive to Sandbanks, wineries and breweries. Includes high speed Wi-Fi, central AC/heat, parking & annual Sandbanks day-use pass.

Superhost

A cozy lounge area is featured within the dome, showing two beige chairs and a textured ottoman. Soft lighting is provided by string lights overhead. Outside, a winter landscape with trees and a hammock is partially visible through the large geodesic windows.

Dome in Plainfield

4.77 out of 5 average rating, 149 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!

Top guest favorite

An industrial-styled tiny home is visible, featuring a red exterior and a gray garage adjacent to it. A wooden deck with yellow chairs offers a welcoming entrance. The landscape is open with bare trees in the background under a clear blue sky.

Tiny home in Prince Edward

4.98 out of 5 average rating, 433 reviews

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.

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, 148 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.

Guest favorite

The studio features a spacious bed with an earthy-toned duvet, complemented by a wooden headboard. A cozy seating area with a vibrant yellow couch is visible in the background, alongside decorative wall elements and plants that add a touch of greenery.

Apartment in Prince Edward

4.9 out of 5 average rating, 205 reviews

Modern open concept farmhouse studio w/parking

Welcome to Unit #3 at the Picton Commons! Located on Main St. near historic Picton Harbour, this mid-century modern studio offers a stylish and cozy retreat for those looking to explore PEC. Our unit features a tastefully renovated interior, complete with a king sized bed, farmhouse kitchen, as well as a private outdoor patio and free street parking directly outside. Steps away from the county fairground and a short walk to the best restaurants and shops Picton has to offer.

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, 112 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

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

4.96 out of 5 average rating, 162 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, 164 reviews

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.