Chalet holiday rentals in Simcoe County

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Top-rated chalet rentals in Simcoe County

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Top guest favourite

Chalet in The Blue Mountains

4.97 out of 5 average rating, 191 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.

Guest favourite

Chalet in Wasaga Beach

4.85 out of 5 average rating, 131 reviews

Amazing lower level suite-Deck on water

This incredible lower level suite on the most beautiful private beach..with deck on the beach and the suite is totally private and has a private entrance and is totally renovated with new downsview kitchen fireplace and private sauna with shower….the location is incredible with private parking spot.. 12 minutes to blue mountain 7 minutes to collingwood and 5 minute walk to the brand new CASINO AND RESTAURANT. This location is perfect for the most incredible beach vacation. BOOK BEFORE GONE…!!

Top guest favourite

Chalet in The Blue Mountains

4.97 out of 5 average rating, 293 reviews

The Little Blue Spruce! pool + free shuttle

Welcome to The Little Blue Spruce Chalet, the place to unwind and rejuvenate. Located 5min from the village, this spacious unit comes with everything you might need to make your vacation carefree: fast internet, cable and multiple streaming channels, lots of linens and towels, a washer/dryer and a fully stocked kitchen. Relax on the back patio watching the birds and bunnies, walk 2 min to the pool or take the free shuttle to the village. Message me for more info! LICENCE NO. LCSTR20220000080

Top guest favourite

Chalet in The Blue Mountains

4.98 out of 5 average rating, 119 reviews

Blue Mountain Escape! Lux 3 bdrm Pool and Hot Tub

STA License #LCSTR20220000018 Fabulous 3 bedroom 2 bath executive suite with premium features, is an upper level end unit townhome located next to the Village at Blue Mountain in the beautiful Rivergrass community. Walk to Monterra Golf Clubhouse and Conference Centre. Steps to the Village featuring award winning restaurants/bars, shops, ski/snowboard hills, mini-golf, biking, hiking, zip lining +. A short drive from the GTA, Blue Mountain is a wonderful year round playground for all ages.

Superhost

Chalet in The Blue Mountains

4.9 out of 5 average rating, 260 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!

Guest favourite

Chalet in The Blue Mountains

4.91 out of 5 average rating, 402 reviews

Modern Ski In/Out Mountain Side Ground Floor

SKI IN AND SKI OUT from the back deck (snow dependent)!! 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

Top guest favourite

Chalet in The Blue Mountains

4.97 out of 5 average rating, 174 reviews

King’s Escape at Blue Mountain

Welcome to our cozy, ground-level, two-bedroom condo in Historic Snowbridge, just a short walk from Blue Mountain Village-your perfect year-round escape! Backing onto Monterra Golf Course, you’ll enjoy stunning views and endless outdoor activities. Ski in winter or hike and bike in summer. Relax at our *seasonal* outdoor pool and take advantage of free rides to the village. Amenities include comfortable sleeping for families, a fully equipped kitchen, and a cozy living space LCSTR20210000165

Guest favourite

Chalet in The Blue Mountains

4.91 out of 5 average rating, 222 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.

Top guest favourite

Chalet in Gravenhurst

4.94 out of 5 average rating, 251 reviews

Log Cabin on the Lake Bed and Breakfast

Log Cabin on the Lake Bed and Breakfast We provide a 1st morning continental breakfast A Lakefront getaway for couples with an amazing view. Experience tiny home living in a custom built Log Cabin. Landscaping provides privacy for all parties (owner next door) we have parking for a boat , with 2 launches within 5 min. One into Morrison Lake the other into the Trent Severn . cross country skiing, ice fishing, water skiing swimming boating. Ready to escape, our Log Cabin could be it.

Superhost

Chalet in Moonstone

4.89 out of 5 average rating, 199 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.

Top guest favourite

Chalet in Coldwater

4.95 out of 5 average rating, 480 reviews

OakRidge Retreat-HOT TUB 100s of acres WIFI

The cottage provides a serene space to share with fiends and family surrounded by nature. Enjoy beaver ponds along the trails, indoor/outdoor games, wood burning stove, sauna, hot tub, firepit, wifi, jetted tub 75" & 55" smart tv's and streaming services. Fully equipped kitchen, double oven, granite counter. In winter, snowshoes and snow saucers. At Christmas the house is decorated and boasts a 15 ft tree. 20-25 minutes from Mount St. Louis ski hill and several beaches.

Superhost

Chalet in The Blue Mountains

4.83 out of 5 average rating, 813 reviews

Blue Mountain / Collingwood Hill Side Condo

Ski To Ski From - Studio Condo with a mountain view. 5 minute walk to the north chairlift. Easy keypad check in. Relax in style in this beautiful, newly renovated ground floor unit located at the newly remodeled North Creek Resort at Blue Mountain. Located minutes from the award winning le Scandinave Spa, some of the most scenic golf courses in Ontario, the condo is also located in one of the province's prime destinations for lovers of wine, craft beer and cider.