Holiday rentals in Wellington

Walk to Beach and Downtown: Wellington PEC Cottage

Stay in the heart of Wellington - steps to the beach, Drake Devonshire, downtown restaurants, and everything Prince Edward County has to offer. Nestled on a peaceful side street, our charming cottage features a cozy fireplace, a fully equipped kitchen, & a large private backyard with BBQ & chiminea. Perfect for families, couples, and groups looking to explore Sandbanks Provincial Park, wineries, breweries and local gems. You're at the center of it all! Relax, unwind, and enjoy your getaway!!

The Trimble Lake House, Ontario

Chic, stylish and well appointed. Welcome to The Trimble Lake House! Steps from the water, any closer and you would be in it. The view from almost every window is of Lake Ontario. Every square inch of this home has been mindfully renovated with attention to detail and quality. Situated in the heart of historic and charming Wellington in Prince Edward County with its many restaurants, cafes and shops. Central to many wineries, Sandbanks Provincial Park and many other points of interest.

Loretta's Loft

In the heart of downtown Wellington, this special place is close to everything. Recently renovated in 2024 heritage building contains character. The space is completely brand new. This open concept unit is spacious and contains a unique second floor loft as well as 2 bedrooms and one bathroom. The unit boasts not only a front veranda with a view of the lake; but also, a spacious deck at the rear to entertain or enjoy an evening in the new seven-person hot tub! STA LIC Number ST 2022-0161

Wellington Guest Suite on Main!

Our 1928 Victorian-style home is on Main Street in Wellington! This offers the convenience of walking out your front door & enjoying our charming village by the water & all it has to offer. Our guest suite is a newly renovated 1 bdrm with lounge area, 1 bath & eat-in kitchenette if you wish to make breakfast/lunch. Enjoy morning coffee or before dinner cocktail on our deck outside the guest suite to take in the great vibe of Wellington & people enjoying this community. License #ST-2023-0009

The Disco Garden Party by The Post Office Motel

Imagine arriving at a secluded mid-century modern retreat, where design and comfort both take first place. You sink into the warmth of your private hot tub, the sky above unfolding into a blanket of stars. Tonight, the Milky Way puts on a show just for you. Later, laughter fills the air as you gather around the fire pit, roasting gooey s’mores with family and friends. Located just minutes to secret speakeasy bars and wine lounges, wineries, the Mustang Drive-In and Sandbanks Provincial Park!

"On the Syde" - GUEST HOUSE

Romantic get-a-way for two! Cozy and sweet, just what the doctor ordered. If you are looking for private, NOT shared space, this little "On The Syde" guest house might be for you! Kitchenette, (CONTINENTAL BF, water, milk, coffee, tea, various small boxes of cereal and juice) TV, WI-FI 6E, Fresh sheets, towels, and quiet at night! Chic Town of Wellington has wineries, nightlife, good restaurants and a local beach just a few minutes away! Book now, singles welcome too! ST-2026-0024

The Meadow House - Prince Edward County Modern

Welcome to The Meadow House! This bright and cozy modern home is nestled in one of the most coveted locations in Prince Edward County. We offer the luxury experience you deserve to truly relax and unwind. Centered among the best wineries, breweries, restaurants, shops, as well as a quick drive or bike ride to Wellington and the Drake Devonshire, our guests can experience all that the county has to offer with ease. You can see more pics @themeadowhousePEC Licence number ST-2023-0107

Design-Forward Luxury Retreat w/ Pool + Hot Tub

Welcome to Valley Road House — a secluded, design-forward retreat in complete privacy, surrounded by nature. Open living spaces and natural light create a calm, elevated feel. Enjoy a sleek chef’s kitchen, curated interiors, and games room. Outside, relax in a heated pool, spacious seating area, and 7-person hot tub. End your day by the firepit under open skies. With no neighbors in sight, this is a rare escape of space, stillness, and quiet luxury. Perfect for groups and families.

Little Ben Prince Edward County

Little Ben's license allows 2 adults and one child age 10 and under. Located 10 feet from Lake Ontario, in the heart of beautiful Wellington, Little Ben is a fully renovated 1 bedroom cottage in the centre of wine country. Little Ben offers a fully equipped kitchen, a dining area and a comfy living area with a wood stove. The true glory of Little Ben exists outside its walls--you are just a mere ten steps down to your own limestone beach on Lake Ontario! Licence # ST-2019-0358

The Red Brick House - Wellington

An original, circa 1860s county home, The Red Brick House combines old world heritage with contemporary design. The bright, welcoming space, sleeps up to six, and is in a prime location just steps away from both Wellington Beach and the Drake Devonshire. While you’re here you can hop on a bike at the rental shop across the street, go explore the beautiful wineries, restaurants, shops, and more. The central location means that you’re close to it all.

Lake Breeze House- Wellington, PEC

Make this your home base in the heart of wine county! 2 blocks to Main St, Creekside Cafe, Midtown Brewing, the Drake, great restaurants, bars, and grocery store. Bring your bike- we're on the Millennium Trail. Walk to Wellington Beach. Minutes to Sandbanks' stunning dunes. Centrally located to wineries. Brand new renovated bathrooms. Large, bright, clean and well equipped spaces make this a great spot for families and friends.

The West Lake House

This luxurious 5 bedroom lakeside retreat is the perfect spot for family and friends to enjoy all that Wellington has to offer. This home on main street is only a short walk to shops and restaurants in downtown Wellington. We are a twenty minute drive from the sandbanks provincial park and provide two vehicle passes for quick access through your stay. You can also drive or cycle to the 26 wineries in our immediate area.