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Cottage holiday rentals in Oakville

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Top-rated cottage rentals in Oakville

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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, 98 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, 139 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, 152 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
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
4.82 out of 5 average rating, 17 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!

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
A wooden dock extends into a serene lake, reflecting a clear blue sky with scattered clouds. Flower pots are positioned on the dock, while torches line the edges, contributing to a peaceful outdoor atmosphere.
Cottage in Richmond Hill
4.94 out of 5 average rating, 166 reviews

White Oak on Wilcox-Richmond Hill Lakefront Oasis

Welcome to The White Oak on Wilcox - a lakefront oasis in the heart of Richmond Hill, perfect for an all-season getaway. Located just 30 mins from Toronto, enjoy direct access to Lake Wilcox with beautiful sunset views from the private dock. This vacation home welcomes you to a relaxing and serene lakefront experience. Surrounded by numerous activities to enjoy year-round, this is the perfect home-away-from-home! Share your memories with us @whiteoakcottageco

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.

Guest favourite
The image features a stone wall prominently displaying the house number '1459'. Behind the wall, a well-maintained grassy area is visible, leading up to a grey cottage surrounded by trees and shrubs. The overall scene suggests a welcoming entrance to the property.
Cottage in Virgil
4.84 out of 5 average rating, 129 reviews

Grape & wine festival - 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 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
Cottage in Niagara-on-the-Lake
4.89 out of 5 average rating, 312 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 cottage rentals in Oakville

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

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!

A hot tub is positioned on a wooden deck, surrounded by a grassy area and vibrant foliage. The bright blue sky overhead contrasts with the greenery and nearby structures, creating a serene outdoor space ideal for relaxation.
Cottage in Niagara-on-the-Lake
4.88 out of 5 average rating, 231 reviews

Hot tub, games and mins to wineries

A contemporary living area is displayed, featuring a sleek gray sofa and a wall-mounted television. Soft lighting illuminates the space, which connects to other rooms through open doorways. A modern electric fireplace is situated beneath the TV, adding comfort to the room.
Cottage in Stoney Creek
4.61 out of 5 average rating, 54 reviews

Lakefront cheerful 2 bedroom cottage house

A serene riverside scene features a well-maintained grassy area leading to a clear water edge. Two adirondack chairs are positioned nearby, under the shade of tall trees. In the background, a two-story house is nestled among the foliage, with a spacious balcony overlooking the landscape.
Cottage in Eden Mills
4.72 out of 5 average rating, 18 reviews

Riverside Retreat

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

Pet-friendly cottage rentals

Superhost
A single-story cottage is shown, featuring a wide wooden deck bordered by green grass. Large sliding glass doors provide ample natural light, while two red chairs are positioned on the deck. The cottage is surrounded by various trees, enhancing the serene outdoor setting.
Cottage in St. Catharines
4.6 out of 5 average rating, 15 reviews

Vineyard Cottage on the Lake on Niagara Wine route

An expansive view of the property reveals a two-story stone house surrounded by lush green fields. A landscaped pathway leads to the entrance, while ample outdoor space and trees provide a serene atmosphere. The surrounding countryside enhances the tranquility of the setting.
Cottage in Limehouse
4.52 out of 5 average rating, 31 reviews

Executive Cottage in a CITY on 100 Acres

Guest favourite
The cottage exterior is characterized by white siding and a black roof. A spacious driveway leads up to the house, which is complemented by a single garage. Trees and open fields surround the property, enhancing a sense of rural tranquility.
Cottage in Niagara-on-the-Lake
4.95 out of 5 average rating, 65 reviews

Tranquil Country Cottage Niagara on the Lake

A detached cottage sits along the shoreline, surrounded by lush greenery. Large windows reflect the soft glow from indoors. A rocky break wall extends along the property's edge, while the calm waters of Lake Ontario create a serene backdrop.
Cottage in Stoney Creek
4.66 out of 5 average rating, 65 reviews

Love on the Lake – Romantic Lakefront Cottage

An aerial view captures the spacious backyard of the cottage, surrounded by lush greenery. A circular fire pit is visible in the center, accompanied by seating. The cottage sits to one side, with pathways leading into the natural landscape, providing a tranquil setting for outdoor gatherings.
Cottage in Belfountain
4.74 out of 5 average rating, 80 reviews

Explore 4BR 3BA Cottage Surrounded By Nature

Superhost
A charming cottage is nestled near the water's edge, framed by blooming cherry blossoms. Green grass surrounds the building, with the blue water visible in the background. Trees provide a natural backdrop, enhancing the serene outdoor environment.
Cottage in St. Catharines
4.67 out of 5 average rating, 30 reviews

Riesling cottage on the lake/vineyard in Niagara

Superhost
A cottage is showcased with a wooden exterior and yellow shutters. The structure features a flat metal roof and large windows. A grassy area surrounds the cottage, with a stone pathway leading to the entrance. Soft green trees frame the scene against a cloudy sky.
Cottage in St. Catharines
4.84 out of 5 average rating, 32 reviews

Lake House Cottage at the edge of the vineyard

Guest favourite
The cottage exterior features a grey siding, complemented by a metal roof. Lush green trees provide shade in the front yard, and a small flower pot adds a touch of color. A gravel pathway leads to the entrance, with a serene body of water visible in the background.
Cottage in St. Catharines
4.92 out of 5 average rating, 13 reviews

Pinot Noir cottage on the lake in Niagara

Private cottage rentals

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

Alton Cozy Riverside Cottage

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

An open living area showcases a comfortable sectional sofa and a glass-top coffee table. The dining space features a table surrounded by six chairs, illuminated by natural light from nearby windows. Neutral walls add to the spacious ambiance of the room.
Cottage in Brampton

202519 Oh Canada! Home Away from Home!

A dining area features a white table surrounded by six ornate chairs with black and white patterns. A light fixture hangs above, illuminating the space. Large windows provide views of the green yard and trees, enhancing the room's openness.
Cottage in Virgil
4.65 out of 5 average rating, 171 reviews

Vintage Wine Time

Guest favourite
A bright living area features a dark television mounted above a white credenza. Two woven chairs are positioned towards the television, each adorned with light throw pillows. Potted plants add a touch of greenery, while framed artworks are displayed on the wall above a low shelf.
Cottage in Parkdale
4.94 out of 5 average rating, 31 reviews

Unique Cottage Hidden in Toronto's Artsy West End

Cottage in Hamilton

Cottage in the City Tree House Retreat

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