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
4.84 out of 5 average rating, 122 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 dining area is depicted with a round wooden table set for four. Light gray chairs surround the table, complemented by decorative placemats. A woven light fixture hangs above, and a door with a window allows natural light to enter. A small closet and a wall-mounted plant holder are visible.
Home in Kingston
4.98 out of 5 average rating, 152 reviews

City Retreat With Board Games

Welcome to our newly renovated detached home! The fully stocked kitchen, smart TV, board games and patio offer convenience and entertainment. Unwind on the patio with high end patio furniture and a barbecue. Enjoy our central location in Kingston for a memorable stay. This property has a garden suite on the back of the property with a separate entrance and backyard space. We look forward to hosting you! Fully licensed for short term rentals with the City of Kingston - License #LCRL20250000092

Guest favorite
A spacious living area features a bold red couch adorned with colorful cushions. A wooden coffee table is centered on a patterned rug. A chair with floral upholstery complements the decor, and soft lighting enhances the warm atmosphere. A doorway leads to a bedroom.
Apartment in Prince Edward
4.87 out of 5 average rating, 280 reviews

The Blues@notes space

Blues@notes is a light and airy space whose decor is inspired by its musical history. The space was formerly owned by a guitar teacher who created the studio for private lessons. Located right in the heart of downtown Picton with all its quaint shops, boutiques, the Regent Theatre, art galleries, unique restaurants and just minutes from the beaches at Sandbanks, the wine route, local craft breweries, cideries, distilleries and mead producers. Also, high speed fiber WiFi covers the whole space.

Top guest favorite
Bungalow in Prince Edward
4.92 out of 5 average rating, 444 reviews

Bright & Cozy Bungalow Close to Downtown Picton

This bright & cozy bungalow is the perfect home base for your PEC getaway! It is centrally located in the heart of Picton, offering 1 bed, 1 bath, office, deck with BBQ & small yard. Comfortably accommodates two adults. Short 5 min walk to downtown, where you can enjoy restaurants, cafe's, boutiques, markets, galleries & more. A short drive to Sandbanks, wineries and breweries. Includes high speed Wi-Fi, central AC/heat, parking & Sandbanks day-use pass (Apr-Nov). STA License #: ST 2019-0177.

Top guest favorite
The open-concept guest house interior features a spacious sleeping area with a large bed. Natural light enters through sliding glass doors and tall windows, illuminating warm wooden beams and light-colored walls. A cozy seating area with two chairs and a table is visible, complemented by decorative plants.
Guesthouse in Bloomfield
4.99 out of 5 average rating, 134 reviews

The Bloomfield Guest House

Are you looking for an awe-inspiring, peaceful, retreat-like setting for your visit to The County? Book this well-crafted private guest-house in charming Bloomfield, perfectly located between Wellington and Picton. The expansive farm-field view will instantly ground and settle your being. Every aspect of this luxury offering has been designed and built with integrity and care. We welcome you to embody a felt-sense of coming home. Follow us @thebloomfieldguesthouse Licence # ST-2022-0076

Top guest favorite
Tiny home in Prince Edward
4.98 out of 5 average rating, 453 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.

Superhost
A welcoming living area features sunlight streaming through large windows. Colorful seating includes a green armchair and an iconic yellow chair, complemented by a stylish side table. A houseplant adds a touch of greenery, and a message board is ready for personalized notes.
Apartment in Prince Edward
4.83 out of 5 average rating, 123 reviews

Funky studio Apt Full kitchen 5 min to Main St

Welcome to our renovated Mid Century Modern private studio apartment. Designed for comfort, functionality and convenience, featuring unique colorful furnishings offering you an alternative hotel stay. The apt is fully equipped for your comfortable stay, featuring a queen bed, full kitchen with new appliances, including a full size stove, microwave and fridge/freezer to accommodate your extended stay. You have your own full private bathroom with walk-in shower and in-suite laundry

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, 152 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, 219 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, 115 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
4.96 out of 5 average rating, 171 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, 167 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