Vacation rentals in Waupoos Island

4.99 out of 5 average rating, 223 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*

5 out of 5 average rating, 188 reviews

Houseboat in Yarker

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!

Superhost

A scenic waterfront view is captured from the cottage, showcasing a grassy area leading to the calm waters of Smith's Bay. A wooden picnic table is positioned nearby, inviting outdoor meals amidst the natural landscape. Trees frame the distant shoreline under a clear blue sky.

Cabin in Prince Edward

4.84 out of 5 average rating, 110 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.

Guest suite in Prince Edward

A serene landscape is depicted, featuring a well-maintained lawn bordered by various trees, including a tall evergreen. A charming dwelling with a porch is visible in the background, bathed in the warm light of a setting sun.

4.94 out of 5 average rating, 138 reviews

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.

4.96 out of 5 average rating, 512 reviews

A spacious bedroom features a large bed adorned with neatly arranged white towels and a gray blanket. Soft natural light enters through a window, complemented by light drapes. Nightstands with lamps are positioned on either side of the bed, enhancing the calming atmosphere.

Guest suite in picton

Westlake’s Suite 25

A beautiful self contained Suite within our home with self check in. A sitting room with kitchenette, leading into a separate spacious bedroom with ensuite. The large windows allow for an abundance of natural light throughout. Relax and reflect on the front porch. Located in the heart of the county, Westlake, which is approx. 15 minutes from downtown Picton. parking included. Walking distance to the Dunes beach at Sandbanks prov. Park.. Sandbanks parking pass included Occupancy 2 adult

A bright living room features a large arched window allowing natural light to illuminate the space. A comfortable white sofa is complemented by a small wooden coffee table and a light-colored accent chair. Sliding glass doors provide access to the outdoors, enhancing the room's openness.

4.93 out of 5 average rating, 235 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!

Place to stay in Prince Edward

4.97 out of 5 average rating, 273 reviews

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!

Apartment in Greater Napanee

A spacious shared yard features a picnic table under an umbrella, red Adirondack chairs, and a fire table surrounded by lush greenery. A barbecue grill is also present against a backdrop of a well-maintained fence, providing a peaceful outdoor setting.

4.97 out of 5 average rating, 154 reviews

Luxurious Victorian Garden Apartment - Explore PEC

Fully private luxury apartment in historical downtown Napanee on the doorstep of Prince Edward County. Offering everything you have been looking for and more. From the moment you arrive you will be taken by the beauty of this regal Victorian property. The apartment has been designed with your comfort in mind. Complete with a beautiful yard perfect for relaxing or dining, and lined with stunning gardens. Perfect for your romantic getaway, wine tour, or city escape.

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.

4.98 out of 5 average rating, 147 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)!

4.99 out of 5 average rating, 159 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.

Guesthouse in Prince Edward

A copper farmhouse sink is featured in a well-equipped kitchen, complemented by a sleek black faucet. Glass containers holding olive oil and hand soap are placed nearby on the counter, while wooden serving trays add a touch of warmth. The open layout connects to a dining area in the background.

5 out of 5 average rating, 206 reviews

thecountycricket, Luxury loft near Picton

Licence No. ST-2019-0357 Welcome to our guest loft at "thecountycricket". I am so sorry but our space is not suitable for infants or children. Our property is 34 acres with 6 acres fenced. We are 10 minutes from Picton Main Street. The loft is 1,200 square foot open concept space with a full coffee station and a cooks kitchen. We live in a quiet street in the country close to town and vineyards, breweries and cider houses.

An outdoor hot tub is positioned on a stone patio overlooking the calm waters of Lake Ontario. The surrounding area features natural greenery, enhancing the serene lakeside view under an expansive sky.

4.97 out of 5 average rating, 134 reviews

Parkway Lake House: Modern retreat w/ hot tub

Newly renovated along the shores of Lake Ontario, Parkway Lake House is the perfectly secluded modern retreat to step away from everyday life yet feel right at home. Gather around with friends and family and enjoy the laidback luxury. The Parkway Lake House was designed by Tiffany Leigh Design and featured on The Globe and Mail, Country Home and the Haven List! Photo credit: Patrick Biller and Christine Reid

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Popular amenities for Waupoos Island vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Waupoos Island

4.85 out of 5 average rating, 221 reviews

Steps to Lake on the Mountain, 10Minutes to Picton

WolfRating, 5 stars3 days ago

We very much enjoyed our stay. The home was well stocked, quiet, and comfortable. I would definitely stay here again and recommend to others.

A fire pit is surrounded by several chairs on a grassy area adjacent to a rocky beach. The calm water of South Bay reflects a clear blue sky. Green trees provide shade, while a cottage can be seen in the background.

4.75 out of 5 average rating, 64 reviews

The Shed End Beach House

ClaireRating, 5 stars1 month ago

The Shed End was perfect for our long weekend stay! The cottage was very clean and cozy, with everything we needed. It’s a quiet spot right on the water and a great location, only a few minutes drive from Picton. Michele and Andy were excellent hosts, very helpful and responsive. Highly recommend this spot if you’re looking for a PEC cottage getaway!

Two red Adirondack chairs are positioned near a stone fire pit, with flames flickering inside. The serene lake reflects a soft pink hue from the sunset in the background, while a grassy area lines the water's edge, enhancing the peaceful lakeside setting.

5 out of 5 average rating, 4 reviews

The Lazy Acre Waterfront Cottage

ReenaRating, 5 stars9 months ago

What a gorgeous place! We had an amazing stay. My family and I went on a wine tour with Tim from Here and There tours. When we got to the Airbnb we enjoyed BBQ and a fire by the lake. Everything was organized so nicely and was spotless! The keurig was a nice addition. We enjoyed our morning tea/coffee by the lake. Would love to come back.

A spacious living area is observed from a loft, featuring a sleek black couch with a light throw draped over the arm. Large windows offer an expansive view of the water, allowing natural light to brighten the space. Sliding glass doors lead to an outdoor deck.

Villa in Prince Edward

4.87 out of 5 average rating, 151 reviews

Serenity Guest House at Lake on the Mountain

KatieRating, 5 stars2 weeks ago

This place was simply perfect! The views are insane, the location is perfect where you’re a 5 min walk from restaurants and 5-10min drive from a tone of local wineries, couldn’t have asked for a better stay in PEC!

A fire pit is positioned on a patio, creating a warm ambiance as flames flicker. A pizza, wrapped in foil, rests on the grill nearby. Bottles of red wine and glasses are placed on the table, with a serene lakeside view and sunset coloring the sky.

4.9 out of 5 average rating, 59 reviews

Tropical waterfront cabin with incredible views

GillesRating, 5 stars8 months ago

Charming accommodation with a superb view and very practical for visiting the region!

Guesthouse in Prince Edward

The kitchen features modern cabinetry with a neutral color palette, complemented by a stainless steel refrigerator and stove. A window provides natural light, while hanging planters add a touch of greenery. Counter space is available for meal preparation, alongside a microwave and coffee maker.

4.83 out of 5 average rating, 30 reviews

Orchard View

SueRating, 5 stars3 days ago

We arrived early for a wedding and Bailly was kind enough to let us in before 4pm. The place was perfect and the view was incredible. The kitchen and bathroom were well stocked and we had access to everything! Definitely recommend this place 100%!!

A bright dining area features a round table surrounded by three wooden stools. Large windows allow natural light to fill the space, showcasing a cozy window seat adorned with colorful pillows. The lush greenery outside is partially visible through the lattice.

4.5 out of 5 average rating, 6 reviews

Waupoos Commons - Beach Front Chalet

AdamRating, 5 stars24 months ago

We had a nice weekend away. We did the wine tours one of the afternoons and it was beautiful to see all the different locations. The beach at the chalet was hard sand and very private. The fishing was great off the dock. Very nice location to just walk from the chalet and see the surroundings. Local people are very friendly.