Cottage vacation rentals in Oakville

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Top-rated cottage rentals in Oakville

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Superhost
The exterior of a modern barn-style building is showcased against a snowy landscape, surrounded by tall trees. The structure features large windows and a dark façade, while a patio area with seating is visible in the foreground, inviting exploration of the winter scenery.
Cottage in Erin
4.83 out of 5 average rating, 100 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.

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, 140 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 spacious outdoor area is showcased, featuring a well-maintained green lawn. The cottage, with a dark roof and blue walls, is complemented by a large wooden deck. A wood sauna stands to the side, creating a serene atmosphere under a clear blue sky.
Cottage in St. Catharines
4.77 out of 5 average rating, 154 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

Guest favourite
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
4.83 out of 5 average rating, 18 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!

Guest favourite
Cottage in Alton
4.81 out of 5 average rating, 21 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

Top 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, 72 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!

Guest favourite
The image captures a serene view of the lakeside property, featuring a lush green lawn that slopes towards Lake Ontario. A sandy beach area and rocky shoreline are visible, framed by trees on both sides and calm turquoise water reflecting the clear sky.
Cottage in Stoney Creek
4.93 out of 5 average rating, 174 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 favourite
A well-maintained cottage exterior is viewed from the driveway, featuring a manicured lawn and a paved path leading to the entrance. A white vehicle is parked in front, with a gravel border outlined by hedges. A small storage shed is visible in the background.
Cottage in Burlington
4.85 out of 5 average rating, 101 reviews

The Pearl Lodge

Almost 1 acre of land for you and your family to enjoy Free parking on premises Beautiful 4 bedroom cottage Comfortably sleeps 10 people Enjoy mini golf, pool table, and table tennis Open concept lounge and sitting area BBQ and firepit available for your use Walkout to deck with beautiful view of massive backyard Covered patio Soccer/Volley ball available upon request Located within minutes to trails, Lake Ontario, shopping and much more.

Top guest favourite
The cottage is surrounded by a lush green lawn, with blooming trees adding color to the landscape. A spacious deck extends from the front of the house, inviting outdoor relaxation. The structure features a charming rustic design complemented by a clear blue sky.
Cottage in Aldershot Central
4.96 out of 5 average rating, 81 reviews

Nature-lovers Cottage Minutes from Downtown

Nestled below the Niagara Escarpment, this unique 4-season cottage offers peace and tranquility. While appealing to nature enthusiasts, with the Bruce Trail accessible from the backyard, this oasis is situated minutes from Downtown Burlington and a hop-skip-and-jump from Toronto and Wine Country. Fur-baby approved with an expansive dog park just down the road, experience all the benefits of cottage country without the crazy commute!

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