Holiday houses in Greater Toronto and Hamilton Area

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Top-rated holiday rentals in Greater Toronto and Hamilton Area

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost

Cottage in Brighton

4.93 out of 5 average rating, 263 reviews

Bianca Beach House - EV/Hot Tub/Firepit/Waterfront

AlexRating, 5 stars6 days ago

Everything about this cottage is perfect. The host thoughtfully provided everything for a great stay. The kitchen is fully equipped—just bring your food. Views from the living room and bedrooms are breathtaking, overlooking the lake with beach-like waves. If it rains, you have board games, vinyls, video games, and a big TV with streaming services by a cozy fireplace and charming decor. Outside, the beach is right by the deck—perfect for morning coffee and peaceful moments. There’s a spa, BBQ, and a fire pit for romantic sunsets. Kayaks are available in the basement; bring your fishing gear (and permit). This is our favorite place so far. It’s walking distance to a waterfront trail and Presqu’ile Park amazing hiking trails, places to picnic, etc by the lake. You’re close to shops and great diners like Counter in Trenton and Whistling Duck in Brighton. This last-minute trip turned into an amazing find. Huge thanks to Jess, our host! We can’t wait to be back.

Guest favourite

Chalet in The Blue Mountains

4.96 out of 5 average rating, 202 reviews

Blue Mountain Getaway!

ErinRating, 5 stars1 month ago

Had a wonderful girl's weekend here. The place was so clean and had everything we needed. Nice and walkable to The Village. Sue was very responsive and gave great local recommendations. Enjoyed having a physically printed book which showcased the features of the unit as well as reminders and stay recommendations. I definitely would not hesitate to book again.

Guest favourite

Home in Fort Erie

4.87 out of 5 average rating, 118 reviews

5* STAR Crystal Beach Lake Erie Niagara Region

PennyRating, 5 stars1 week ago

It was a beautiful, clean, and easy-to-find home. The location was perfect—walking distance to our Dad's place. We would love to go back again. The host was responsive and provided all the necessary information we needed in a timely manner.

Superhost

Home in Tiny

4.68 out of 5 average rating, 225 reviews

Private log cottage on 2 acres

DanaRating, 5 stars1 week ago

We recently held our annual family birthday weekend at Natalia's place with a multi-generational crew that spanned 1.5 years to 90 years young! This incredible log cabin met all of our needs. The bedroom on the main floor meant an accessible space for our great aunt, the games room in the basement was such a fun space for our teens. The sliding doors to the wide front porch and the giant yard with fire pit, play structures and trampoline gave us lots of space to play. Plenty of fridge and freezer space and bathrooms on every level was really helpful. Natalia was very responsive and kind as a host. Balm Beach is gorgeous and walkable. There are some really cute restaurants and coffee shops close by (shout out Cawaja General Store and Balm Beach Bar & Smokehouse!) No place is perfect - I note the stairs to the basement are rather steep, and a few suggestions were shared with our awesome host, including about kitchen amenities, but this is a pretty spectacular place to stay for a group.

Superhost

Condo in Innisfil

5 out of 5 average rating, 4 reviews

Luxurious 2-Bed, 2-Bath Furnished - 5 Star Resort

MitchellRating, 5 stars4 months ago

When we walked into Jacqueline's place it was like wow!!! Open concept,bright and loved the decor and the top to floor windows. Jacqueline was very accomadating and very responsive. Would highly recommend her place and we will definitely be back in the future!!! Thanks for being a wonderful host

Holiday rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Popular amenities for Greater Toronto and Hamilton Area holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Greater Toronto and Hamilton Area

Guest favourite

Home in Wasaga Beach

4.89 out of 5 average rating, 109 reviews

20 min from Blue Mountain -Relax & Enjoy Winter

TawnyaRating, 5 stars1 month ago

Such a great place to stay after skiing at Blue Mountain! Definitely recommend.

Guest favourite

Home in Forestville

4.85 out of 5 average rating, 84 reviews

Quiet Country Escape

MeganRating, 5 stars3 weeks ago

This cabin is beautiful!!! Large open floor plan! Windows all over so no matter where you are on the house you have a view of the beautiful creek and woods. The porch and fire pit were great to grill out and eat while listening to the creek rushing by and seeing all the deer and animals. If you are looking for a quiet secluded place to get away and relax, this is definitely the place to rent! Even put up some decor for the special occasion we went there for!

Superhost

Townhouse in The Blue Mountains

4.88 out of 5 average rating, 178 reviews

Private condo getaway at base of Blue Mountain

FrancoisRating, 5 stars1 month ago

Great place very Cozy. Krista is a great host. We keep this place in mind for a future trip in this area

Superhost

Home in Buffalo

4.85 out of 5 average rating, 20 reviews

Urban Getaway

DanielRating, 5 stars4 months ago

Melissa was a great host and communicated throughout. Very understanding and helpful. I would recommend this host.

Superhost

Home in Toronto

4.7 out of 5 average rating, 93 reviews

Stunning Bright 2+ Bdrm Luxury w/Free Parking

John And IlsaRating, 5 stars3 months ago

This is our second time staying here, and Arti's place was perfect for our group of 3 adults, a toddler and a baby. The Beltway proved to be a wonderful alternative to walking on icy sidewalks our first evening and had a wonderful peaceful ambiance as opposed to roads and traffic. The place is exactly as advertised and we would not hesitate to stay here again.

Superhost

Home in Wasaga Beach

4.88 out of 5 average rating, 50 reviews

COZY Cottage steps away from the beach.

SharonRating, 5 stars5 months ago

Andreina was a great host. I booked her place for a guest of ours and she was quick to answer any questions and was really accommodating to our guest who had pets. Her place was in a great location, private but not too far from town. The house was just as the pictures said and kept really clean, she made our guest feel right at home! I would recommend her place and I look forward to working with her again in the future!!

Top Guest favourite

Townhouse in The Blue Mountains

4.98 out of 5 average rating, 192 reviews

Hidden gem! Amazing, Corner-unit

ElisângelaRating, 5 stars1 month ago

We truly felt at home and loved the place. It was exactly as described and shown in the photos. We found everything that we needed at the house. The shuttle was a commodity that made our stay even more comfortable. Kady and James were wonderful hosts, making our experience even more memorable.

Guest favourite