Cottage holiday rentals in Oakville

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Top-rated cottage rentals in Oakville

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Superhost

Cottage in Erin

4.83 out of 5 average rating, 106 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 depicted with vibrant colors. The blue house features white trim, a balcony, and decorative elements, while the adjacent yellow house displays inviting features and a porch. Lush greenery and blooming flowers add to the pleasant setting.

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 nestled within a lush green landscape, surrounded by a variety of shrubs and flowering plants. The red-brick façade and dark roof are complemented by a tall chimney, while the inviting entrance is framed by greenery.

Cottage in High Park North

5 out of 5 average rating, 15 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 stone-clad façade of the cottage presents a charming entrance, complemented by natural landscaping. The pathway leads up to a welcoming front door, flanked by shrubs and decorative plants. A cabin can be seen to the left, enhancing the inviting outdoor atmosphere.

Cottage in Lincoln

5 out of 5 average rating, 141 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

The exterior features a spacious backyard with a wooden deck and lush green grass. A traditional wood sauna is placed beside a seating area, complemented by trees and clear blue skies in the background. Sunlight brightens the scene, creating a serene outdoor setting.

Cottage in St. Catharines

4.78 out of 5 average rating, 166 reviews

Winter Lakeview Spa Niagara w/ 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, 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.

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

4.86 out of 5 average rating, 21 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

A sandy beach area features four red Adirondack chairs arranged around a circular stone fire pit. The shoreline of Lake Ontario is visible, with greenery lining the background under a partly cloudy sky.

Cottage in Stoney Creek

4.92 out of 5 average rating, 181 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

The spacious terrace features wooden decking with a railing that offers views of the surrounding greenery. Sunlight creates patterned shadows on the floor, enhancing the outdoor space's inviting atmosphere. Lush trees provide a natural backdrop, contributing to the serene environment.

Cottage in Richmond Hill

4.94 out of 5 average rating, 168 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 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

4.85 out of 5 average rating, 132 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

The exterior of a spacious cottage is presented, featuring a welcoming entrance with double doors framed by large windows. Neatly trimmed hedges and colorful flower pots add to the aesthetic. The concrete path leads to the front, emphasizing the property’s well-maintained landscape.

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

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, 326 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.