Pet-friendly holiday rentals in Wellington

The Cozy Postmaster’s House PEC w/ new Hot Tub!

EXCITING NEWS: our HOT TUB has now been installed at the house - relaxing and just for you! Escape to the birthplace of wine in Prince Edward County at the historic Postmaster's House in Hillier. This charming 3-bedroom house from the 1890s offers a cozy fireplace and is surrounded by over 40 vineyards. Explore wineries, restaurants, breweries, North Beach, Millennium Trail, and Wellington village, all just a bike ride away. Unwind and immerse yourself in the beauty of this idyllic destination.

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.

Prince Edward Landing

Victorian Home in PEC gets a full renovation to become a one of a kind vacation home. Featured in the Globe & Mail the house is a 2018 restoration of old-world charms with as many contemporary comforts as one wishes. From the gorgeous landscape and a screened-in, white-trim front porch to the fully modern spectacular interior The back of the house is a stunning starkly contemporary black box, designed by architect Jay Pooley, a lecturer at the University of Toronto’s school of architecture.

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

Octagon House - Garden Cottage Pet Friendly

Nestled in the heart of Picton, this charming garden cottage offers comfort and convenience. Just a short stroll to the county’s best restaurants and close to the Millennium Trail for nature walks. A quick drive to Macaulay Mountain or the beaches of Sandbanks National Park, with a complimentary pass. After a day of exploring, relax in the cozy king bed with soft cotton linens. Enjoy your private backyard with a patio, hammock, and enclosed yard for your dog. Your perfect retreat awaits!

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.

Dragonfield House: a beautiful stay in central PEC

Dragonfield House: STA License No. ST-2024-0206 Featured in Canadian House and Home, March 2015, Dragonfield House was designed with a contemporary approach to country living. It is a four bedroom split-level country house, plus a guest yoga retreat with all the amenities of a city home. It features a heated salt-water pool (Mid May until Mid October) and a brand new year round hot tub for six people! There are three work/desk areas within the house ideal for remote working.

Charming Cottage in Wellington’s Heart near Beach!

Nestled on a peaceful side street in the heart of Wellington, our charming cottage offers the perfect retreat for families, couples, or group getaways. You're just steps from Wellington Beach, popular restaurants, and vibrant local gems like The Drake, Midtown Brewery, and more. Whether you're exploring top wineries, breweries or distilleries, relaxing on Sandbank's sandy beaches or dining at award-winning restaurants, our cottage puts you at the center of it all!

Private Backyard, Hot Tub, Dog Friendly, Central

We invite you to stay in our professionally designed 3-bedroom suite located in Wellington, PEC. Close to Main Street, a 20-minute drive to Sandbanks. This space has a private hot tub, stocked kitchen, 2 bath, dining + living room and laundry. Wake up and head to our favourite cafes in Wellington, enjoy a walk to Wellington Beach, go for a drink at a local brewery, or dinner at one of the nearby restaurants on Main St. We’ll send a guide with our fav places.