Holiday Homes in Greater Toronto and Hamilton Area

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Top-rated Holiday Homes in Greater Toronto and Hamilton Area

Guests agree: These holiday homes are highly rated for location, cleanliness and more.

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Top Guest favourite
A large table is set on a grassy area, adorned with white dishware and a green glass vase filled with flowers. In the background, a wooden sauna and a shed are surrounded by lush greenery under a clear blue sky.
Holiday home in Niagara-on-the-Lake
5 out of 5 average rating, 213 reviews

Top 5% Sauna | Bocce Ball | Vineyard Views | NOTL

Welcome to Vineyard Views, a modern farmhouse nestled on half an acre in Niagara wine country! Renovated in 2022, this raised bungalow is a five minute drive to Old Town NOTL. We are minutes to numerous wineries & all that Niagara-on-the-Lake has to offer. Our beautiful home is set up for watching stunning sunsets, hosting guests and is perfect for both families & friends. A backyard oasis with a sauna, bocce ball court, conversational circle, patio dining set, large lawn, BBQ, privacy & more!

Guest favourite
A modern living space is presented, featuring a large kitchen island with bar seating. A comfortable couch, accented with decorative pillows, is positioned near a wall showcasing circular wall art. Natural light floods the area through expansive windows, creating a bright atmosphere.
Holiday home in Innisfil
5 out of 5 average rating, 51 reviews

Innisfil Resort - 3 Bed Condo Amazing Views

Make some memories at this unique marina/boardwalk neighbourhood. It is a family-friendly place 4 season getaway, with lots of activities, walking trails, bike rentals, water sport rentals, entertainment and fabulous restaurants. 3 bedrooms, 2 bathrooms, modern kitchen with large island, big comfy couch! Enjoy the extra large South East Balcony over looking the Marina and the Boardwalk. Comes complete with a fully stocked kitchen, bbq and parking. You will feel right at home on your getaway.

Superhost
A newly built two-story townhome features a modern design with large windows allowing natural light. The structure is complemented by a landscaped front area with young trees, and a lamppost adds charm to the sidewalk in front of the entrance.
Holiday home in Niagara Falls
4.78 out of 5 average rating, 73 reviews

Townhomes at the Falls - 310 A lower - Buffalo Ave

Enjoy a stylish experience at this conveniently located Brand New Built Townhome Suite. Just 2 Blocks from the World Famous Niagara Falls State Park, this fully furnished and equipped home is perfect for your Niagara Falls Vacation. This home was built in August 2022 and offers two bedrooms with 3 beds (sleeps 6) a spacious open layout living room and kitchen and huge bathroom. Across the street from the NF State Park it is walking distance to the Falls Attractions and Casino! 310 A (lower)

Guest favourite
Holiday home in Hamilton
4.87 out of 5 average rating, 146 reviews

The Waterfront Oasis – Views, Firepit & Hot Tub

Escape To Our Beautiful Waterfront Retreat With Stunning Lake Ontario Views. Enjoy A Luxurious Travertine Stone Living Room With A 65" Smart TV, And Cook In A Fully Equipped Chef’s Kitchen With Stainless Steel Appliances. Step Outside To A 3-Tiered Stone Patio Featuring A BBQ, Firepit, And Hot Tub—Perfect For Sunsets And Starry Nights. You'll Have Full Private Access To The Home, Barbeque, Patio, Hot Tub, And Direct Lake Access. Ideal For A Relaxing, Memorable Getaway With Family Or Friends.

Guest favourite
A bright living area features a spacious couch and a cozy armchair draped with a yellow blanket. A television is positioned on a media console, and a kitchen with modern appliances is visible in the background. Warm wood flooring adds to the welcoming ambiance.
Holiday home in Mississauga
4.9 out of 5 average rating, 110 reviews

Cosy Private Basement Apartment

You and your family will be close to everything when you stay at this centrally located place. Lisgar Go Train/bus Station that goes to downtown Toronto. This house backs to a public park. It's a wonderful place to enjoy amenities like the splashpad, swings, soccerfield etc. Grocery, restaurants and shops are just 3 mins by car or a 10 min walk. Toronto downtown 45 mins Niagara falls 1hr 30 mins Blue mountains 2 hrs Toronto premium outlets 7 mins Squareone mall 19 mins Port credit 25 min

Top Guest favourite
A living area features a sleek black television mounted on a rustic brick wall. A wooden coffee table sits below the TV, accompanied by a small plant. A light area rug with a circular design complements the space, while a cozy bed is positioned to one side.
Holiday home in Toronto
4.94 out of 5 average rating, 70 reviews

Cozy modern 1-bedroom suite

Guests will be close to everything when you stay at this centrally located place. 8min walking distance to the subway, easy access to streetcars and buses, in a family-friendly residential neighbourhood. Situated near several parks (splashpads, skating rink, public pools), bike paths, 10min drive to the beach, 10min subway ride to Yonge/Bloor, walking distance to a plethora of restaurants, coffee shops and local retailers (Danforth/Greektown, Riverdale, Leslieville, Beaches, Little India).

Guest favourite
A charming log cabin is nestled among green grass and trees, featuring a contrasting black and white exterior. Flower boxes filled with vibrant blooms adorn the windows, and a red door adds a welcoming touch. The nearby lake is visible in the background.
Holiday home in Kawartha Lakes
4.88 out of 5 average rating, 59 reviews

Charming Cottage on Quiet bay of Sturgeon Lake

This memorable place is anything but ordinary. A charming 1850 Log Cabin in a sheltered bay of Sturgeon Lake. Enjoy bonfires, Spectacular sunsets and a glass of wine while floating on your picnic table. Spend your days on the water in a paddle boat, stand up paddle board, kayak & canoe. Fishing and Pontoon boat rentals available. Great swimming, fishing and boating from your own private dock will make for memories of a lifetime! Minutes away from golfing, shopping and fine dining.

Top Guest favourite
A bright bedroom layout features two double beds adorned with white linens and green accents. A small seating area is visible, including a gray chair and decorative plants. Adjacent, a second room presents a king bed with navy walls, complemented by stylish wall art and plush cushions.
Holiday home in Barrie
5 out of 5 average rating, 45 reviews

Entire House, Luxury Cozy Family Retreat w/ 5 Beds

Welcome to our stunning modern house in the serene west end of Barrie. This beautifully decorated home boasts 4 spacious bedrooms, each equipped with 5 cozy, hotel-quality beds. Ideal for families, friends, or business travelers, our home offers a perfect blend of comfort and convenience. Each bedroom boasts unique decor, providing positive vibes and a calming atmosphere. Located close to the Waterfront, ski resorts, parks, and local dining. 📩 Message us for an exclusive discount!

Guest favourite
An open-concept living area is presented, featuring a comfortable gray sofa complemented by decorative pillows. A modern coffee table sits at the center, while large windows provide ample natural light. Soft curtains frame the windows, and a TV is mounted on the wall across from the seating.
Holiday home in Toronto
5 out of 5 average rating, 11 reviews

Bright 1-Bedroom Near Lake & Downtown Toronto

Welcome to your cozy home away from home in the heart of South Etobicoke. This bright and modern 1-bedroom apartment is located above a quiet med spa and clinic, offering a peaceful stay with unbeatable convenience. Just steps away from local cafes, restaurants, bakeries, and parks. Enjoy a quick 10min drive to the lake, 15min to Downtown Toronto, easy access to the highway and public transit making it a breeze to get anywhere.

Superhost
A circular living room features a combination of gray sofas accented with yellow pillows and a coffee table made of natural wood. Large windows allow natural light to fill the room, and a cozy atmosphere is enhanced by side tables and a lamp on either side.
Holiday home in Ravenna
4.46 out of 5 average rating, 124 reviews

The Beehive w/ Hot Tub, Sauna & Fireplace

The Beehive is a Blue Mountain landmark. This dome-shaped chalet is adorable & Instaworthy! Compact and cozy inside, the chalet has 6 bedrooms + a sofa bed accommodating groups of up to 14 guests. The circular living room in the loft is a unique space to gather and connect. Conveniently located at the top of the North Chair & just minutes away from Scenic Caves & Blue Mountain Village.

Top Guest favourite
A charming exterior view of a recently renovated home is captured at night. Soft light illuminates the entrance and windows, while snow gently covers the surrounding area. The welcoming porch features wooden railings and steps leading to the front door, framed by trees in the background.
Holiday home in Niagara Falls
4.96 out of 5 average rating, 111 reviews

Gorgeous Gem in Niagara’s Wine Country

A newly renovated, well appointed artistic home. Centrally located near the Falls, Niagara Parkway, Niagara-on-the-Lake, casinos, wineries and the largest outlet mall in Canada. (A car is recommended since the closest public transportation is 2 km away.) A great gathering spot in any season with a full kitchen, laundry and outdoor space ready to entertain family and friends.

Guest favourite
The exterior of a modern A-frame retreat is showcased, featuring a triangular façade with large windows. A small porch is equipped with two wooden chairs and a side table, inviting relaxation while enjoying the surrounding greenery and scenic views.
Holiday home in Lincoln
4.88 out of 5 average rating, 162 reviews

Cozy A-Frame Retreat in Niagara Wine Country

Our 1950s A-frame retreat offers 3 bedrooms, 2 baths, a renovated kitchen, and stunning views of snow-dusted vineyards and the Niagara Escarpment. Enjoy cozy nights by the fire, explore winter winery tours, or snowshoe scenic trails nearby. Perfect for a romantic getaway or family trip, this serene yet central location is your ideal winter retreat.

Popular amenities for Greater Toronto and Hamilton Area holiday homes

Destinations to explore