Vacation rentals in Waupoos Island

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Top-rated vacation rentals in Waupoos Island

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Guest favorite

Guesthouse in Prince Edward

4.99 out of 5 average rating, 173 reviews

thecountycricket, Luxury loft near Picton

Licence No. ST-2019-0357 Welcome to our guest loft at "thecountycricket". We built and designed it with guests in mind. Our 34 acres is on a peaceful street with the woods lining the back of our property. Six acres are fenced in for our dogs and dog guests. We are 10 minutes from Picton Main street, vineyards, breweries, cider houses, antique shops & restaurants. Our loft is a large open-concept with a king size bed, pull out queen sofa & a full cook's kitchen. Welcome to our home in The County.

Jan 21 – 28

G$36,945 GYD per night

Guest favorite

Guest suite in Marysville

5.0 out of 5 average rating, 157 reviews

Waterfall Retreat-Hot Tub-3rd Night Free until May

Listing description *ALL INCLUDED* ( with seasonal variations) HotTub~4 Watercraft~Park Pass~Bikes~Outdoor Fire & Shower~Veggie Garden A one-of-a-kind experience awaits you in our 200 year old converted limestone mill. This eclectic space with a private entrance is nestled between two waterfalls on an island in the Salmon River. The beautifully appointed 525 sq ft suite is right on the edge of the river. Dine & relax on your private patio overlooking the waterfalls and the old one lane bridge.

Feb 5 – 12

G$32,022 GYD per night

Guest favorite

Guest suite in Prince Edward

4.99 out of 5 average rating, 292 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.

Jan 2 – 9

G$18,993 GYD per night

Guest favorite

Guesthouse in Prince Edward

4.85 out of 5 average rating, 262 reviews

The Edge. Stunning view. EV Friendly

This private cabin and deck has a stunning view of Adolphus Reach from the top of a 200' escarpment. The property is located right beside Lake on the Mountain Provincial Park. Have a look on Google Maps. Two eating establishments are within walking distance. Many more are less than 10km away. Day use at Sandbanks must now be reserved. Text me for details. I'm required to charge HST if you choose to book via Airbnb but not otherwise. Posted price includes HST. Licence ST-2019-0310

Oct 3 – 10

G$29,630 GYD per night

Guest favorite

Bungalow in Prince Edward

4.91 out of 5 average rating, 323 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.

Nov 14 – 21

G$20,417 GYD per night

Guest favorite

Yurt in Yarker

4.99 out of 5 average rating, 307 reviews

Our Yurt - Your Getaway. Rustic Luxury!

Reconnect with nature all year round at our enchanting yurt. Perfect for a romantic holiday. Nestled in the woods, directly across the road from the lake, it is private but not secluded. Your stay includes outdoor leisure equipment for fun on the lake every season. Just relax, I do the dishes! There's no running water in the yurts well-appointed kitchenette but everything else you need is there! The toilet is in an outbuilding by the yurt and a gorgeous guest shower room is up at the house.

Apr 2 – 9

G$27,864 GYD per night

Guest favorite

Home in Prince Edward

4.92 out of 5 average rating, 189 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!

Nov 15 – 22

G$73,256 GYD per night

Guest favorite

Guest suite in picton

4.96 out of 5 average rating, 420 reviews

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. Walking distance to the Dunes beach at Sandbanks Provincial Park. Parking spot and Sandbank’s Pass included. Occupancy 2 adults

Jan 29 – Feb 5

G$22,639 GYD per night

Guest favorite

Cottage in Prince Edward

4.99 out of 5 average rating, 106 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)!

Oct 9 – 16

G$55,624 GYD per night

Guest favorite

Apartment in Prince Edward

5.0 out of 5 average rating, 148 reviews

Speakeasy Suites Picton, Prince Edward County

Whether you’re looking for a quiet, cozy, and comfortable stay, or if you’re an avid Instagrammer searching for a modern vacation experience, this luxury two-bedroom, fully-loaded suite in central Prince Edward County is the stay for you. Steps away from Tim Hortons, 555 Craft Brewery, The County Canteen, and many other popular local spots, you’re not far away from the experience that has made Prince Edward County the go-to tourist spot in Ontario!

Dec 29 – Jan 5

G$19,457 GYD per night

Guest favorite

Cottage in Prince Edward County

4.99 out of 5 average rating, 123 reviews

Peaceful Peninsula. A Private Waterfront Oasis.

Please note June 28-July 27) is 7 night minimums(Saturday to Saturday). 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.

Jul 24 – 31

G$158,569 GYD per night

Guest favorite

Bungalow in Milford

4.87 out of 5 average rating, 239 reviews

Royal Road Cottage

Experience the calm and beauty of looking out over the fields, and taking in the endless sky. Whether you're wine-tasting, cycling, bird-watching or seeking quiet retreat, Royal Road Cottage brings you to the heart of it. The cottage is rustic, cozy, and comfortable. 20 minutes from all regional attractions, it offers a quiet spot, off the beaten path. Great for couples, solo travellers and small families. We require a 2 night minimum.

Jul 20 – 27

G$28,048 GYD per night