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, 242 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, 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 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, 330 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, 253 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

4.93 out of 5 average rating, 427 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

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, 436 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.

Top guest favorite

A fire table is centered on a wooden deck, surrounded by vibrant autumn foliage. A comfortable chair with a patterned cushion is positioned beside the table, inviting relaxation. The tranquil waters of the Bay of Quinte are visible in the background under a clear sky.

Cottage in Prince Edward

4.95 out of 5 average rating, 200 reviews

Desta, A perfect home base to explore the County.

A quaint, and private getaway for those looking to unwind and recharge all four seasons. Enjoy views of the Bay of Quinte from your deck while sitting by the fire table, the front deck or the living room. Conveniently located a short drive from downtown Picton, Sandbanks Provincial Park & surrounding wineries. Minutes away from Lake on the Mountain and it's delightful restaurants. You will find Desta conveniently located to take full advantage of all that Prince Edward County has

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, 149 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, 207 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, 113 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

The exterior of the newly renovated coach house is shown, featuring a blue facade and a welcoming front entrance. A yellow bench sits beside the door, and a planter with colorful flowers adds a touch of charm. Lush greenery surrounds the property, enhancing the serene atmosphere.

Cottage in Prince Edward

4.95 out of 5 average rating, 347 reviews

Lola's Loft, -NEW Coach House-Picton PEC

Located just steps from Main Street Picton, this newly renovated coach house is hidden away in a large fenced in green space. While cozy and rustic, the house is equipped with a large modern bathroom and full kitchen. A short walk takes you to all the great shops and restaurants Picton has to offer. Relax on your private deck after a long day at the beach.Enjoy the use of a SANDBANKS PARK PASS which allows you free access to all the beaches and to bypass any lineups.

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, 163 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)!