Vacation rentals in Waupoos Island

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Top-rated vacation rentals in Waupoos Island

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Top guest favorite

An aerial view captures the schoolhouse situated amidst lush greenery. A private patio features a hot tub surrounded by wooden decking and outdoor seating. The well-maintained landscape includes pathways and a firepit, highlighting the serene outdoor space adjacent to the home.

Home in Prince Edward

4.99 out of 5 average rating, 241 reviews

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*

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

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, 252 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, 425 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.

Top guest favorite

A charming wooden bungalow is set amidst lush greenery, featuring a welcoming porch and a well-maintained yard. Tall trees provide shade and add to the serene atmosphere, while a garage is visible in the background, enhancing the rustic character of the property.

Cottage in Prince Edward

4.95 out of 5 average rating, 279 reviews

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

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, 206 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 County

4.99 out of 5 average rating, 165 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.