Chalet vacation 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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Guest favorite

Chalet in Priceville

4.91 out of 5 average rating, 448 reviews

ReLive Hilltop Chalet w/brand-new hottub, sunrises

Relive Retreat's Hilltop Chalet is a 700 sq ft open concept rustic cabin w/high ceilings, full-length windows, spring water, private + new hot tub, fireplace, BBQ, wrap around deck w/views, hiking trails + more. Perfect for couples, friends or families looking to relax & rejuvenate in nature. If peace is what you are looking for this is it! Occassionally dog friendly so please inquire first. This is a private 72 acre retreat. We live here with our 2 dogs, currently hosting 2 yurts and 2 cabins.

Sep 24 – Oct 1

G$33,777 GYD per night

Guest favorite

Chalet in The Blue Mountains

4.96 out of 5 average rating, 149 reviews

Entire Rustic Chalet - Hot Tub, Sauna, Large Yard!

This updated chalet in the heart of Blue Mountain surrounded by forest includes a huge front yard, balcony, hottub, sauna, pool table, darts, foosball and is only a 3min drive to the BM Village. The great room has an amazing Polk audio surround sound with 70"4k TV ideal for movie nights after a long day skiing. 5 of the 7 bedrooms have there own 32"TVs for more private entertainment before bed. The mattresses are very comfy for a quality sleep so you will be well rested for the next day of fun.

Nov 9 – 16

G$126,672 GYD per night

Guest favorite

Chalet in The Blue Mountains

4.91 out of 5 average rating, 297 reviews

Modern Ski In/Out Mountain Side Ground Floor

SKI IN AND SKI OUT from your own personal back yard deck!! Notice the amount of comfortable seating for NINE PEOPLE around the TV that many other places are without. At the end of a long ski day having a comfortable place for everyone to sit is what most Chalets are missing. Enjoy our family’s beautiful renovated GROUND FLOOR chalet with 2 Bedrooms, 2 Baths, 6 Beds conveniently located next to the Blue Mountain Inn. Blue Mountain Village is a 7 minute walk away. Location, Location, Location!

Oct 19 – 26

G$46,986 GYD per night

Guest favorite

Chalet in The Blue Mountains

4.87 out of 5 average rating, 117 reviews

Luxury Chalet 1/Hot tub

Welcome to our bright and spacious 6 bedroom 2 storey detached Swiss Style Chalet with private HotTub and magnificent views of the Mountains. It comfortably accommodate up to 16 people. Nicely renovated-new kitchen, furniture, bedding and much more new. Ideally located at the base of the mountains with a direct walking path to the Village and ski slopes at end of cul-de-sac (600m), 4 min drive to the beaches, 8 minutes drive to Collingwood and 25 minutes drive to Wasaga Beach. LCSTR20210000236

Sep 11 – 18

G$95,783 GYD per night

Guest favorite

Chalet in The Blue Mountains

4.93 out of 5 average rating, 209 reviews

Relax at The Mountaintop Chalet (sleeps 16)

Blue Mountains Accredited Short-term Accommodation License # LCSTR20210000110 Whether you’re looking for a romantic escape, planning a family reunion or special event, Mountaintop Chalet will fit all your vacation needs. Our rustic and secluded Chalet is a short drive to Blue Mountain Village and the world-renowned Scandinave Spa right down the road, you will not find a more central place to call home while exploring. Our property is just under one acre with lots of space for fires & fun!

Apr 20 – 27

G$211,595 GYD per night

Guest favorite

Chalet in The Blue Mountains

4.9 out of 5 average rating, 162 reviews

Cosy Chalet - 4 Season Family Oasis

Welcome to Snowbridge chalet, our sunny, 4-season private retreat. Professionally designed and decorated, the chalet is the perfect getaway for families, only a 10 minute walk or 3 minute drive to all the ski & snowboarding activities and fun of Blue Mountain village. With room enough for 6 guests, our 2 bed, 2 bathroom ground level chalet backs onto Monterra golf course, providing lots of space for outdoor time and bbq's. Includes all the comforts of home for the perfect relaxing escape.

Oct 8 – 15

G$44,547 GYD per night

Superhost

Chalet in Phelpston

4.88 out of 5 average rating, 283 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.

Mar 9 – 16

G$112,970 GYD per night

Superhost

Chalet in Hawkestone

4.77 out of 5 average rating, 216 reviews

Charming Cottage near Lake Simcoe

During the winter you can experience a lot of fun snow can offer. Enjoy alpine and cross-country skiing, tubing, snowboarding, snow shoeing, fat biking or snowmobiling. Best Ontario ski resorts withing minutes to drive. During the summer: Enjoy a swim at the lake or bring your own boat to explore. Sit by the fireplace inside or build a bonfire outside. Kid friendly family paradise. Beautiful bike trails in the woods. Bike to Orilia or Barrie through the scenic old railway trail.

Dec 31 – Jan 7

G$31,123 GYD per night

Guest favorite

Chalet in Grey Highlands

4.94 out of 5 average rating, 106 reviews

Private 5 Acre Chalet with Bunkie & Sauna

An enchanting, private, 4 season retreat in the escarpment atop Beaver Valley, metres from a beautiful section of the Bruce Trail. The property has nearly 5 acres with cut trails, hammocks, and a sports field. It has two buildings connected by a large deck that has outdoor furniture and a BBQ. The sauna is just feet away. The buildings are fully outfitted offering a comfortable base for daily adventuring, or a stay put retreat. This spot is ideal for a family, or a couple's getaway.

Sep 18 – 25

G$26,133 GYD per night

Guest favorite

Chalet in The Blue Mountains

4.97 out of 5 average rating, 181 reviews

The White Cedar Chalet pool/free shuttle

The White Cedar Chalet For your perfect family vacation in Blue Fully stocked kitchen with lots of extras provided 🫖☕️🫙🍽🥂 🛌 5 comfy beds Lots of extra pillows, blankets, towels, cozy linens 🍼 Highchair, Pack n Play, toddler bed 🛀2 bathrooms including Whirlpool tub 🖥 2 TVs with Netflix, Prime, Disney+, Crave and Cable🍿 💻Fast internet, office nook 🚒Toys♟️games 🎲 Xbox 🎮 🔥Gas BBQ on the balcony 🔥Gas Fireplace 🚗Parking in shared lot NO. LCSTR20230000108

Jun 30 – Jul 7

G$124,394 GYD per night

Guest favorite

Chalet in Moonstone

4.93 out of 5 average rating, 176 reviews

Beautiful bright four season chalet, Mt St Louis

Enjoy the perfect getaway all year round in our Chalet. Located right by Mount St Louis ski resort in Moonstone and only minutes from Horseshoe Valley. Our Chalet consists of 2 bedrooms, 1 up & 1 on the main floor with a loft equipped with 1 queen bed. The property backs onto forest offering guests amazing scenery and tranquility. Enjoy a variety of winter activities including skiing, snowboarding, snowshoeing or curling up beside the fireplace practicing yoga or meditation!

Jun 2 – 9

G$53,952 GYD per night

Superhost

Chalet in Moonstone

4.89 out of 5 average rating, 235 reviews

Private Luxury Chalet at forest’s edge

10YO 4 bedroom chalet with BELL FIBE high-speed Internet package only 3 mins from Mt St Louis Ski Hill. Our kitchen/dining/living area is designed as 1 big open space that leads onto a 16' X 30' deck overlooking the forest. It's great for couples, adventurers, families (with kids) and groups. Private trails from our lot, skiing, snowshoe, biking/hiking, 5' X 8' Pool table, darts. Well-behaved dogs welcome. For things to do in area search 'the chalet moonstone' on Youtube.

Apr 1 – 8

G$50,338 GYD per night