Chalet holiday rentals in Greater Toronto and Hamilton Area

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Top-rated chalet rentals in Greater Toronto and Hamilton Area

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Top guest favourite
Private room in Mansfield
5 out of 5 average rating, 84 reviews

Swiss Inspired Room with Private Ensuite - Loghaus

This is our Swiss inspired Room, it features a King bed plus couch that turns into an additional Queen bed. Complete with private ensuite with a jetted bathtub ! Our picturesque custom built Log Home is located at the top and next door to the Mansfield Ski Club - we are offering two rooms each with Continental Breakfast. Local activities include; biking, hiking, golfing, breweries & more ! 30 mins to Barrie and Wasaga Beach. 45 mins to Collingwood / Blue Mountain. 1.5 hours north of Toronto

Top guest favourite
A warm living area features leather sofas adorned with soft throws, along with a daybed lined with colorful cushions. A cozy wood stove is positioned nearby, providing a focal point. Natural light streams through the glass doors, complemented by rich purple curtains.
Chalet in The Blue Mountains
4.91 out of 5 average rating, 98 reviews

Stylish Log Chalet w/ Hot tub Minutes to Village

A real gem! Warm & inviting, our 3 bdrm chalet comfortably sleeps 8 & offers an upscale setting for your special Blue Mountain getaway. Decorated with a mix of vintage & modern to provide the very best comfort, we offer a 6 person Hottub on our south facing upper deck, Gourmet Kitchen, Spa Bathroom, 3 Smart TVs, WiFi, Laundry, Propane BBQ, & so much more. Come with families, friends, or just the 2 of you, to relax & put your feet up. In the country yet 2 minutes from town. You'll love it!

A spacious country home is set against a clear blue sky, featuring a modern design with a dark exterior and a metal roof. Expansive grassy areas surround the house, and tall trees in the background provide a sense of privacy and seclusion.
Chalet in Singhampton
5 out of 5 average rating, 16 reviews

FireSong-A stunning family friendly country home

A family friendly country home nestled in a Canadian forest close to Collingwood and the Blue Mountains. Lots of space to relax (with 2 hang out spots!) and unwind after being outside hiking, biking and more! Have a feeling of being off the grid while being close to amenities, having reliable internet access and just over 90 mins from Toronto. Enjoy preparing meals in the gourmet kitchen, relax with your family in the entertaining space and end your evening with games, a fire or a hot tub.

Top guest favourite
A well-lit sunroom features large glass windows that overlook a lush green landscape. Comfortable seating is arranged with decorative cushions. A wooden coffee table and a decorative plant add a cozy touch to the inviting space.
Chalet in Clarington
4.95 out of 5 average rating, 63 reviews

Yozy Retreat-*Private Pond*Brimacombe*CTMP*

Carved out of the Ganaraska Forest, the Yozy Chalet is a stones throw from the city, come here to find, recapture or create your best self, and moments. The Yozy Chalet is open concept with a full kitchen, two bedrooms and living dining space. Come here to enjoy nature, the hot tub, the restful view, the pond or the walkable forest. Two streams hug the property, twisting and turning catching your eye as you walk across one of the three bridges to our forest that borders horse stables.

A spacious outdoor area includes a large swimming pool surrounded by a stone patio. The house features a wall of glass windows, allowing natural light to flood the interior. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting.
Chalet in Phelpston
4.84 out of 5 average rating, 343 reviews

Dream Home Oasis; 7 bedroom, Hot Tub Swimming Pool

Our place is perfectly situated on a radius of just minutes travel to lakes, beaches, ski hills, ATV's and snowmobile and hiking trails nearby. Near Horseshoe Valley, Wasaga Beach and the Muskokas, you have the convenience for a quick trip or choose not to leave our place that offers all the amenities of a perfect holiday oasis, a Solar Heated Swimming Pool for the summer and a Hot Tub all year long. In the middle of Nature, you have the quiet and secluded ability to appreciate it all.

Top guest favourite
A serene pond reflects vibrant autumn foliage, with trees transitioning from green to shades of yellow and orange. A gentle fountain adds tranquility to the scene, while a spacious outdoor area is visible in the background, surrounded by colorful trees.
Chalet in Mulmur
5 out of 5 average rating, 42 reviews

Country Oasis - 5 private acres with hot tub

Escape to the country and unwind. Just 1.5 hours from the city, this luxurious chalet sleeps up to 12 and offers a hiking loop, a 1-acre swimming pond, volleyball, ping pong, a trampoline. (Or work with ease thanks to high-speed wifi.) With ski clubs, Bruce Trail hiking, cycling, and snowmobile routes right outside the door, boredom is not an option. Venture up to Collingwood, hop down to Hockley Valley, or just soak up the tranquility from the hot tub. **Ask about Mon-Fri discounts**

The chalet is nestled among lush greenery, with a stone exterior and a spacious deck. Stairs lead from the gravel path to the entrance, framed by vibrant shrubs and trees. The wraparound deck showcases a blend of natural elements and inviting outdoor spaces.
Chalet in Creemore
5 out of 5 average rating, 6 reviews

Spacious chalet near Creemore

This spacious chalet near Creemore comes with a huge deck for enjoying fresh air & summer breezes, plus nearby hiking, cycling and beaches. It has 5 bedrooms, 3 bathrooms, 2+ living rooms, all on a quiet dead-end street. The Bruce Trail / Noisy River Provincial Park is around the corner, it's minutes to Creemore's shops and just a short drive to Wasaga Beach. Leave your stress behind as you escape to the country. Minimum 7-day rental. Unfenced yard, pets to be confirmed with owner.

A spacious living area features a large sectional sofa, complemented by a round coffee table and a textured area rug. Soft lighting emanates from recessed fixtures and a decorative pendant light. A wall-mounted artwork adds visual interest to the neutral color scheme.
Chalet in Terra Cotta
4.79 out of 5 average rating, 14 reviews

18 Acre Cozy and Relaxing Chalet with HOT TUB!!

Forget your worries in this spacious and serene space by the riverside situated on 18 ACRES. Enjoy the hot summer days, colorful Fall leaves or the cozy and magical Winters. Relax on one of 2 decks or on in the Hot Tub Spa. Perfect place for family gathering or large outdoor event (Inquire separately). Riverside Estates is located just less then 10 mins for the 410 N Hwy. This 3 bedroom (sleeps- 1 queen, 2 singles beds) furnished and decorated chalet with fully equipment kitchens

Guest favourite
A spacious living area is visible, featuring large windows that overlook the lake. A cozy sectional sofa is positioned within, accentuating the open layout. A modern kitchen island with a stovetop is seen in the foreground, with decorative items adding character to the space.
Chalet in Youngstown
4.85 out of 5 average rating, 80 reviews

Lakeside Cedarshake chalet|EV Charge|Niagara Falls

Experience the perfect winter getaway at this spacious 4-bedroom lakeside chalet overlooking the peaceful shores of Lake Ontario. Just minutes from Niagara Falls, this inviting retreat is designed for cold-weather comfort with radiant heated floors, cozy living areas, and panoramic lake views. Enjoy crisp winter mornings by the water, relax after exploring wineries and trails, and unwind in a warm, private setting ideal for families, couples, and groups.

Top guest favourite
A historic log cabin is nestled among lush green trees, with sunlight filtering through the foliage. The building features multiple windows, and the surrounding lawn is well-kept, with a small seating area visible near the cabin's entrance.
Chalet in Port Perry
5 out of 5 average rating, 81 reviews

Historic Log Cabin with all Amenities

This beautiful and historic log cabin displays all original axe huewn logs and sites on 300 acres of private property only 1 hour from downtown Toronto! from your doorstep you have access to ponds (10 minute walk) , mtn biking, xcountry skiing and hiking trails. All of this is contained on this private property. This beautiful cabin is rustic yet fully equipped with a full kitchen, bathroom, fire place, loft bedroom, and lots of comfortable seating.

Chalet in Collingwood
4.8 out of 5 average rating, 5 reviews

Blue Mountain Winter Stay · Lakeview Escape for 12

Welcome to this Full Home Winter’s Theme retreat, a warm and spacious getaway for up to 12 guests seeking comfort and connection. With serene lake views, multiple living areas, cozy fireplaces, reading corners, and an outdoor fire pit for snowy evenings, this home offers a calm, inviting atmosphere. Just minutes from Blue Mountain Village and close to the Scandinavian Spa, perfect for relaxing and reconnecting this holidays and winter season.♥

Chalet in Toronto

Casa Athena — Luxury Toronto Mansion with Gym

Welcome to Casa Athena — a 5 bedroom, 5 bathroom, 5000+ sqft luxury mansion located in one of the best neighbourhoods in North York. With 4 stories of space, this home combines classical Greek elegance with modern comfort. Perfect for families, corporate retreats, or intimate gatherings. 5 minutes walk to Yonge street and just minutes from highways, shopping, and a short drive to downtown Toronto. ** Parties are strictly prohibited **

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