Cottage vacation rentals in Oakville

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Oakville

Guests agree: these cottages are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Top guest favorite
A modern living area features two white chairs and a plush gray sofa, accompanied by a gold coffee table atop a soft area rug. Decorative elements include potted plants and a neon sign, while bright light streams through the windows, illuminating the open kitchen in the background.
Cottage in Niagara-on-the-Lake
4.96 out of 5 average rating, 263 reviews

The Coupe: A Hip Wine Lovers Retreat in NOTL! ✌️

Finally! A hip place to stay in Niagara-on-the-Lake. ✌️😎 Welcome to "The Coupe", a contemporary wine lovers retreat in the heart of the Niagara wine region! Located just 400 metres from the lake and Ryerson Park, the perfect picnic spot with stunning sunsets and views of the Toronto skyline. And walking distance to all of the amazing restaurants, shops, and entertainment in the Historic Old Town, and of course... just minutes to some of the best wineries in Canada. Time to pop the bubbly! 🥂🍾

Guest favorite
A charming, dark blue cottage is framed by lush greenery and vibrant purple flowers. The cobblestone pathway leads to a bright yellow front door, welcoming guests. Various flowering plants provide color and texture to the well-maintained garden, enhancing the inviting exterior.
Cottage in Niagara Falls
4.96 out of 5 average rating, 346 reviews

Charming Carriage House in Niagara's Wine Country

A converted carriage house and former blacksmith shop with a rich history dating back to the 1800’s - updated with brand new modern amenities. This is a one level plus loft bedroom, ideal for those who have challenges with stairs. Centrally located near the Falls, Niagara Parkway, Niagara-on-the-Lake, casinos, wineries and the largest outlet mall in Canada (car recommended). A great gathering spot in any season with a full kitchen, laundry and outdoor space ready to entertain family and friends.

Guest favorite
A charming cottage-style home is set within a manicured garden, featuring decorative shrubs and colorful flowers. The exterior showcases a mix of blue siding and a warm red door, framed by two distinctive bay windows. Steps lead to the inviting entrance, enhancing the overall appeal.
Cottage in Grimsby
4.95 out of 5 average rating, 40 reviews

Grimsby Beach Cottage

Enjoy a day at a quiet hidden beach followed by a night around the bonfire in this charming, cottage-style home. With this convenient location, you’ll appreciate the city-like accessibility, located minutes from public beaches and a close drive to wineries, hiking trails and the quaint town of Grimsby with an array of restaurants, pubs, and cute shops. Minutes from the Bartlett highway exit, you’re also only a short drive from Port Dalhousie, downtown St. Catharines, Niagara Falls and Hamilton.

Top guest favorite
A charming cottage is illuminated softly at night, featuring a sloped roof blanketed in snow. Warm lights glow from the windows, outlining the brick facade. Snow-covered landscaping adds to the serene winter atmosphere in front of the home.
Cottage in High Park North
5 out of 5 average rating, 19 reviews

The Cottage in High Park - free Parking

Escape to our city oasis! Nestled in High Park/Bloor West Village, our charming cottage offers urban tranquility just 15 mins from downtown by subway. Ride a bike to the beach, wander the tree-lined streets, explore boutiques in the local village, or forest-bathe deep in the trails of High Park. Return to cozy comfort, a wood-burning fireplace, a game of charades, or step out to a covered patio, perfect for BBQ creations or a movie under the stars. Your urban-cottage escape begins here!

Top guest favorite
A cozy living area features a leather sectional sofa adorned with decorative cushions. A gas fireplace is situated against a rustic stone wall, complemented by wooden shelves housing potted plants. A flat-screen TV rests on a wooden stand, and inviting lighting is provided by a side lamp.
Cottage in Lincoln
5 out of 5 average rating, 142 reviews

The Stone Cottage in Vineland

Relax in this two bedroom three bathroom home that comes with a fully-equipped kitchen, dining room, laundry, and spacious living room with gas fireplace. Enjoy access to a beautifully landscaped backyard, with private deck overlooking acres of quiet farmland. The perfect modern day getaway, The Stone Cottage sports up-to-date amenities that combine with the peacefulness of country living, to create the ideal vacation retreat, within easy reach of everything the Niagara Region has to offer!

Guest favorite
The bedroom features a spacious bed dressed in soft linens, complemented by decorative pillows. A cozy throw lies across the end of the bed. Natural light enters through windows adorned with minimal coverings, while a ceiling fan provides comfort. A bedside table offers a lamp, enhancing the serene environment.
Cottage in St. Catharines
4.92 out of 5 average rating, 85 reviews

Niagara Oak Lane Cottage, Private w/outdoor Patio

A studio style cozy one floor cottage with a gas fireplace warming the room, leading to a private outdoor patio, viewing the tennis court. The cottage is on wine route, bike route, close to the city, & the new hospital but in the country. Very Private. Queen size new bed. New shower and renovated bathroom. Fully equipped kitchen with fridge, stove, coffee maker, tea kettle, dishes, and of course... wine glasses. Easy access to the highway,Niagara on the Lake &Niagara Falls. Amble parking.

Top guest favorite
A charming red cottage features a welcoming front porch with wooden steps leading to the entrance. White window frames and flower pots with seasonal blooms enhance the front yard, bordered by well-kept greenery and a stone pathway.
Cottage in Niagara-on-the-Lake
5 out of 5 average rating, 135 reviews

Nancy's Guest Cottage-Perfect for a Spring Getaway

A perfect get-away cottage located in old town Niagara-on-the Lake. Only steps away from Ryerson Park on Lake Ontario. Enjoy the use of the entire cottage for a weekend of exploring Niagara's many wineries and micro-breweries, playing golf, or taking in a play at the Shaw Festival. At the end of the day dine at one of the many restaurants in town or prepare your own meal in the fully equipped kitchen. And if your car's electric don't worry...an EV charger is available right on the property!

Top guest favorite
Two large outdoor couches with plush cushions are arranged around a woven coffee table, situated on a brick patio. Lush greenery provides a natural backdrop, creating a serene outdoor setting perfect for relaxation.
Cottage in Lincoln
4.97 out of 5 average rating, 201 reviews

Chestnut Cottage

Quaint Cottage in the heart of wine country. This is a recently renovated 4 bedroom, 2 bathroom house. Basement was just finished in 2021. The house is bright and clean and furnished with a modern country farmhouse feel. WIFI, cable TV, Netflix, full kitchen and central a/c are just some of its amenities. This house would be great for couples, a group of friends or even a family looking for a relaxing getaway in the country, but still close enough to numerous activities for all to enjoy.

Guest favorite
A charming two-story cottage is set against a backdrop of Lake Ontario. The home features a stone and wood exterior, with a long, paved driveway leading to a double garage. Trees line the property, providing a natural frame to the serene lakeside view.
Cottage in Stoney Creek
4.92 out of 5 average rating, 186 reviews

Lake Front Heaven - Gateway to Niagara/Vineyards

A magical cottage with its own beach house on Lake Ontario. This place is special! The beach house an extra bedroom and full bath which is available during the spring/summer months. There’s a pier, boat slip, fire pit, picnic table and plenty of outdoor seating. All of this 50 minutes from downtown Toronto, 40 minutes from YYZ International airport and 25 minutes from the world famous Niagara falls. The scenic is a great base to explore the Niagara region. Operator License 24-305205

Guest favorite
Cottage in Parkdale
4.95 out of 5 average rating, 38 reviews

Cottage in Toronto’s West End •Walk to BMO Field•

A hidden cottage retreat in Toronto’s vibrant west end—just 15 minutes walk to BMO Field with no traffic or crowds. Tucked away on a quiet, tree-lined laneway, this fully renovated 1800s cottage offers a rare mix of charm, privacy, and location. Enjoy the energy of the city—Queen West, Ossington, Liberty Village —then come home to your own peaceful escape. Perfect for World Cup visitors, families, and remote workers. Stay close to everything, without sacrificing calm and comfort.

Guest favorite
Cottage in Virgil
4.85 out of 5 average rating, 132 reviews

The Merlot Cottage

🏡 Escape to Elegance at the Merlot Cottage, 1459 Niagara Stone Road! 🍇 Unwind in our stunning short-term rental in the heart of Niagara-on-the-Lake! Enjoy modern comforts, beautiful surroundings, and easy access to wineries, dining, and historic sites. ✨ Book your getaway now and experience the charm of Niagara! ✨ Perfect for couples, families, or a friends’ retreat. Your unforgettable vacation starts here! 🌟 License number is 080-2021

Guest favorite
An outdoor hot tub is nestled beneath a wooden pergola, featuring jets and seating. In the background, a swimming pool is visible, surrounded by greenery and blue skies, evoking a relaxing atmosphere.
Cottage in Niagara-on-the-Lake
4.89 out of 5 average rating, 329 reviews

Modern Farmhouse XL Hot Tub NOTL 15Mins- Falls

Indulge in the rejuvenating health benefits of a mid-week retreat at our Outdoor Spa. Immerse yourself in the refreshing autumn ambiance, relishing the crisp cool air, snug days, and enchanting evenings amidst the fragrant scents of fall in our picturesque outdoor setting. Discover the myriad ways to savor the essence of fall at our spa. Unwind with an overnight stay at our Modern Farm House in charming Niagara-on-the-Lake.

Popular amenities for Oakville cottage rentals

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Halton
  5. Oakville
  6. Cottage rentals