Vacation rentals in Waupoos Island

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Top-rated vacation rentals in Waupoos Island

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Guest favorite

The image shows a multi-level home with a light-colored exterior and balconies. A landscaped area with stone seating surrounds a central fire pit, bordered by vibrant orange flowers and green grass, providing an inviting outdoor space.

Chalet in Prince Edward

4.88 out of 5 average rating, 148 reviews

Chalet On The Bay at Waupoos w/ Hot Tub

Relax and unwind at Chalet On The Bay in beautiful Waupoos. Located just 10 minutes from Picton the property is ideally situated as a hub for accessing all the County has to offer. A new home w/ hot tub that features cathedral ceilings, loft style master and all modern finishes with a rustic feel. A great space for family outings, wine touring or a getaway with friends. Please note we DO NOT have access to water off of our property and don't allow parties or pets. Home is on private road.

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Guest favorite

This two-story cottage is framed by large trees, featuring a welcoming front porch with white railings. The exterior is a mix of dark and light siding, with a red front door. A spacious lawn extends in front, leading to a view of the water.

Cottage in Deseronto

4.86 out of 5 average rating, 202 reviews

County Waterfront, Newly Renovated: Glenora House

Welcome to The Glenora House, a newly renovated cottage in one of the best waterfronts of Prince Edward County. Located in Adolphus Reach, the cottage is 2 minutes away from the Glenora Ferry (free) which takes you in 10 minutes to Prince Edward County. Ferry crosses every 15 mins in summer, 30 min otherwise. 15-35 mins drive to Picton, Bloomfield, Wellington and Sandbanks Prov Park as well as vineyards and restaurants. Msg Jennifer (Prop Manager) or Ricardo for questions. Jul/Aug 1 wk min

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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

4.93 out of 5 average rating, 305 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!

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Top guest favorite

An aerial view captures a spacious waterfront area featuring a gray concrete patio. Bright red outdoor chairs surround a fire pit on the grass, while a sauna is positioned nearby. The cozy retreat is nestled among trees, with direct access to the water.

Home in Bath

4.93 out of 5 average rating, 105 reviews

Lakefront with Sauna & Trails

Escape to our serene Lake Ontario retreat, nestled on a gated property with westward views. Enjoy a sauna, indoor fireplace, and outdoor fire pit. Features three bedrooms, two bathrooms, a fully-equipped kitchen with modern appliances, high-speed FIBE internet, and a 50" TV. Located at the quiet end of a cul-de-sac, just 15 minutes from Kingston and steps from walking trails. Ideal for a romantic getaway or a family vacation, sleeps up to 8 with plenty of parking. Your lakeside oasis awaits!

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Top guest favorite

The cottage is situated along the shoreline of Consecon Lake, surrounded by lush greenery. A spacious deck extends from the cottage, offering access to a seasonal dock. A pool is visible on the deck, enhancing the outdoor space along the water.

Cottage in Consecon

4.94 out of 5 average rating, 275 reviews

Lakefront Cottage with Pool, Hot Tub & Sauna

Welcome to your Prince Edward County getaway! Our Muskoka-style lakefront cottage with pool, sauna and hot tub was custom-built in 2004. Perfect for families and very private, it comfortably sleeps 8 adults with additional room for children (10 years and under). Located on the edge of Consecon Lake, we're 13 mins from Wellington & close to many wineries. We've been Superhosts since 2017, and our family would love to welcome you to our little slice of paradise. STA License #: ST-2019-0223.

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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, 180 reviews

Peaceful Peninsula. A Private Waterfront Oasis.

Please note summer bookings (end of June-end of August) 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

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Guest favorite

Home

4.89 out of 5 average rating, 194 reviews

Cozy PEC Retreat

Mya’s Place is designed for rest, quiet, and reset. In the winter and early spring, Prince Edward County becomes peaceful and uncrowded, perfect for couples, remote workers, creatives, and anyone needing space to slow down. Cozy interiors, calm energy, and everything you need for a true escape. Drive to downtown Picton or the beautiful Sandbanks Beach in under 30mins. A provincial parks pass has been provided for your convenience. STA #2024-0187 R1

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Guest favorite

Home in Prince Edward

4.95 out of 5 average rating, 38 reviews

The Avalon on the Lake - Swim, Sip & Explore

Welcome to your lakeside retreat, where style meets tranquility. This scenic property offers a harmonious blend of modern finishes and natural beauty. The spacious interior features an open-plan living area with panoramic lake views, creating a serene backdrop. Outside, enjoy the dock and decks, perfect for entertaining or simply soaking in the stunning views. With direct lake access and meticulously landscaped grounds, this home is a haven for relaxation and quality time.

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Top guest favorite

Bungalow in Prince Edward

4.99 out of 5 average rating, 127 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

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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, 196 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)!

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Guest favorite

The charming exterior of a converted church is presented, showcasing a striking red brick facade and a steeply pitched roof. Tall trees and lush greenery surround the building, adding to the serene setting. A welcoming entrance with a dark door and steps leads to the front.

Home in Prince Edward County

4.97 out of 5 average rating, 310 reviews

The Prince Edward County Church, A Unique Escape

Stunning 1888 converted church in Prince Edward County on a private 2.3-acre waterfront property backing onto the Bay of Quinte. This one-of-a-kind stay blends soaring ceilings and historic charm with modern luxury. Sleeps 8 adults with 4 bedrooms, lake views, direct waterfront access, high-speed WiFi, Sonos, fireplaces, kayaks, and more. Featured in Forbes, House & Home & Cottage Life with over 300 guest reviews.

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Guest favorite

A modern kitchen space is highlighted by light cabinetry and a sleek stone countertop. Pendant lights hang above a dining area with woven chairs. A vase of dried flowers adds texture to the scene, complemented by carefully arranged kitchen essentials.

Cottage in Prince Edward

4.98 out of 5 average rating, 171 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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