Cottage holiday rentals in Oakville

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Top-rated cottage rentals in Oakville

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Superhost

A serene view of a heated pool surrounded by a well-kept yard. The clear blue waters of Lake Ontario are visible in the background, framed by a green fence and lush greenery, including trees and shrubbery, enhancing the outdoor experience.

Cottage in Stoney Creek

4.69 out of 5 average rating, 36 reviews

Breathtaking Sunsets n Lakeview’s are calling!

Escape to a blue wonderland.This home will make for an enchanting & exotic getaway. Luxurious Lake views,sunsets, a large 10ft heated pool will drown you in pure extravagance. Spend your holidays in this beatific home,stroll the large yard & relax in the Hottub &Sauna listening to the soothing sound of the water & its murmuring waves bewitch you with tints of blue. A stay here will leave an unwavering mark upon your heart asthe memories, adventures and moments created here will be unforgettable.

Guest favourite

A serene outdoor area features a spacious wood deck with a hot tub, patio furniture, and a large umbrella. The sauna, resembling a wooden barrel, is positioned nearby. A far view reveals the barn structure and seating area under a pergola, surrounded by lush greenery.

Cottage in Erin

4.85 out of 5 average rating, 88 reviews

Private oasis in Erin.Hot tub & Woodburning sauna.

WOOD BURNING SAUNA & HOT TUB⭐️ONE OF A KIND, 1800 sq. ft BARNDOMINIUM on 18 acres of total privacy! Serene, country getaway in the picturesque countryside of Erin⭐️Full-size kitchen,harvest table,spotless bathroom, couch & chairs set infront of the floor to ceiling glass doors⭐️Cozy loft with tv, comfy queen bed & oversized couch. ⭐️Soaring trees & trails,grain bin bar on concrete pad with fire-pit, tables & chairs.Wood deck with patio set.Separate cabin with double bed. You won’t want to leave!

Guest favourite

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, 39 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.

Superhost

An outdoor dining area is set up with a large table surrounded by several chairs. A gazebo provides cover, and the tranquil backdrop features a view of Lake Ontario during sunset, with greenery and yard games visible in the distance.

Cottage in Stoney Creek

4.84 out of 5 average rating, 186 reviews

Lakeview Oasis: EV Charger, Fire Pit, Sunset View

Relax in our tranquil Lake Ontario retreat, nestled in Stoney Creek between Toronto and Niagara Falls. Our cottage boasts lake views year-round, a backyard oasis with a fire pit, outdoor furniture, and yard games. Indoors, enjoy recent renovations including billiards, ping pong, Smart TV, and board games. Sleeps six with two bedrooms and a sofa bed, fully-equipped kitchen, modern bathroom, laundry, free Wi-Fi, and parking. Create unforgettable memories in our cozy and tastefully decorated home.

Guest favourite

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, 14 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 favourite

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, 137 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 favourite

A vibrant sunset is depicted over Lake Ontario, with colors of orange and yellow reflecting on the water's surface. Silhouettes of trees are visible in the foreground, adding depth to the tranquil scene.

Cottage in Lincoln

4.93 out of 5 average rating, 72 reviews

COZY LAKESIDE COTTAGE IN THE NIAGARA WINERY REGION

A beautiful cottage nestled in the heart of Niagara's wineries and steps from Lake Ontario. A warm and inviting space with full amenities such as granite countertops, stainless steel appliances, central A/C and heated floors. Located in a quiet mature neighbourhood, just minutes away from Niagara Falls, historic Jordan Harbour and a short drive to Toronto! Watch the many species of birds from the front yard or stroll through the wineries across the road and in the area. All Yours to Discover!

Superhost

An inviting lakefront cottage is showcased under a colorful sky at dusk. A spacious driveway leads to a dark blue exterior with contrasting elements. The landscape includes trees and a nearby building, adding to the serene setting.

Cottage in St. Catharines

4.77 out of 5 average rating, 149 reviews

Lakeview Spa Niagara Hot tub and Sauna

An Exquisite lakefront oasis, this home is situated on the shores of Lake Ontario. Enjoy a cedar sauna, hot tub soak while watching the sunsets, looking out over the lake and stunning evening views of the Toronto skyline. Our Cottage is pure serenity and within fifteen minutes from all that Niagara has to offer, making it one of the best vacation rentals in Niagara Cottage contract filled in and signed required. No smoking inside the home or near windows/doors license number 22106298STR

Superhost

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, 83 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.

Superhost

A heated hot tub is situated under a wooden gazebo, surrounded by bare trees and a snowy landscape. Steam rises gently from the water, creating an inviting atmosphere for relaxation in the serene outdoor setting.

Cottage in Brampton

4.8 out of 5 average rating, 15 reviews

Rustic 5BR Cottage | Cozy Hot Tub+ Autumn Backyard

Escape to nature in our private 5BR and 4WR riverside cottage – perfect retreat for groups with premium amenities! ✓ Entire cottage to yourself – full privacy! ✓ 5 spacious bedrooms with 6 double beds and 4 washrooms ✓ Cozy Family & Living Rooms ✓ Fully equipped kitchen & High-Speed Wi-Fi ✔ Dining area with seating for 8 guests ✓ Private Backyard with hot tub & Indoor games ✓ Scenic riverfront setting near Eldorado Park ✓ Safe neighborhood Book your stay and make unforgettable memories!

Superhost

Cottage in Alton

4.8 out of 5 average rating, 20 reviews

Alton Cozy Riverside Cottage

Discover tranquility at our country cottage by the Credit River in Caledon/Alton. A short stroll to Canadian Open Golf course. Steps from downtown Alton's dining and culture. Moments to Millcroft Spa and Alton Mill events spaces. 2 mins to Osprey Links Golf Course main clubhouse. Explore Upper Credit trails nearby. Enjoy a private fire pit and river view seating, balancing country peace with nearby activities. Propane tank available $30. Video tour of cottage on insta @alton.cottage

Guest favourite

A garden path lined with stepping stones leads to a view of the Toronto skyline across the water. Green grass and plants surround a patio table and chairs, providing a serene setting with trees framing the picturesque scene.

Cottage in Toronto

4.94 out of 5 average rating, 71 reviews

Toronto Island Cottage

This beautifully furnished, bright, and airy cottage is located just eight minutes south of the city, on the picturesque Toronto Island. This is a unique opportunity to experience all that the islands offer in a stylish setting. Perfect for a staycation or vacation, the cottage is well-equipped with everything you need to make the most of your time. The serene community is accessible only by ferry or water taxi. The view of the Toronto Harbour and skyline is absolutely epic – enjoy!