Smoking-friendly holiday rentals in Grey Highlands

IRIE Paradise Beach Cottage

Welcome to Irie Paradise, your home away from home. Relax with the entire family at our comfy four season home. In the summer enjoy a short walk to Ontario's longest freshwater beach. Take a walk along white sandy beaches, great for children with it's shallow shores or watch a spectacular sunset during the evening. In winter months, you may enjoy exploring our picturesque communities less than 30 mins away. You will find beautiful scadinavian Blue Mountain for all snowboarding & spa luxuries.

S07 Nature Heaven at the Farm: Cabin on The Lake

One of a kind unique & unmatched experience Your cabin with two large windows will face a quiet semiprivate lake, enjoying sunsets on the water. On the opposite side, you will relax to the sounds of birds and mesmerized by 150+ feet tall maple trees canopy. Walk and follow the gravel road to see 200+ goats with their babies in the background. On a clear night, you’ll see the Milky Way, a pure magic and fairytale experience. Stay with us for three+ days and recharge. Our reviews say it all

Serenity, Simplicity and Stone

This is a tiny cottage in a sleepy little hollow that opens onto the Georgian Bay. Inside, each stone was carefully chosen and the woodwork was built, piece by piece, by two craftsmen who are highly skilled and passionate about repurposing. It's an art that will leave you in awe; especially if you're worried about climate crisis. The coat hangers are upcycled 100-year-old railway spikes! If you're looking for luxury you will be disappointed but if you're a minimalist you're going to love it.

Tiny Home Camping for 2 with Hot Tub & Outhouse

Experience a unique winter camping retreat for two in our wood-stove-heated tiny home. Complete with an outdoor shower, outhouse, covered hot tub, and a propane BBQ for cooking. The campfire pit and picnic table sitting area are open all year. This holiday rental setup is designed for couples and located on our working hobby farm right off a main highway. * Please note, the outdoor shower and bar closes seasonally due to freezing temperatures with no alternative available. Reopens May 2026.

Large chalet/3 King, 8 bedrooms/Large Hot Tubs

Escape to our stunning vacation chalet, where contemporary meets cozy charm. This spacious and cozy chalet offers the perfect retreat for families, friends, or groups seeking both relaxation and adventure. Inside, the chalet features a perfect blend of some modern upgrades and inviting, rustic touches, making it an ideal home base for your getaway. One of the highlights of the property is the large, year-round swim spa and hot tub. Swim spa area will be amazing to cool down in the summer.

JJ’s small town country retreat

Take a step back in time to this old farm house. Located on the corner of our little town called Badjeros. This house was built in the 1930s and it’s been in our family for over 80 years. Since then there has been numerous upgrades to the house as well as a large 1200 square foot open concept addition built onto the existing house. While out in the country, this house is central to many attractions in the area 1.5 hours south of Toronto/GTA. Blue Mountain/ Collingwood is 30 minutes north.

Experience Country Living at Firefly Ridge

Your private living space is comfortable and bright, with lots of picturesque windows and high ceilings. There is a walkout to a private area where you can relax, and unwind, enjoying the sounds of nature and some farm animals, such as horses, minis, donkeys, goats, chickens, cats, 2 Australian cattle dogs and even some piggies. We love our animals and we welcome yours as we are a pet friendly farm. PLEASE NOTE DOGS MUST BE ON A LEASH WHILE ON THE PROPERTY.

Entire Guesthouse - Forest Retreat, Starlink WiFi

Relax and unwind at this private getaway surrounded by peaceful woodland. California King bed and blackout curtains so you can ease into your morning with birdsong and the scent of fresh forest air. Refresh with a hot shower or relax in a clawfoot tub in your own spacious private bathroom. 3 acres of private woodland is yours to enjoy with easy access to the scenic Bruce Trail. Free parking, fast Starlink Wi-Fi, and a 50" Smart TV for cozy movie nights in.

Private Camp Site

Beautiful camp site for rent outside Maxwell ON. Close to many beautiful trails (Hoggs Falls, Eugenia Falls, Old Baldy, Scenic caves, ect.). 1/2 an hour from Collingwood. Bring your camper / camping gear and enjoy a peaceful stay on 150 acres of private property a short distance off the dirt road. There is also a pond and trails on the property. There is a latrine on site, but there isn't any hookups for water or electricity right now.

Peaceful country getaway

A beautiful above-garage apartment with huge windows and a spacious, open concept main living area encourages connection and comfort. Our space is ultra family friendly with an abundance of games, puzzles, and toys for kids but has everything the adults need to have fun as well. Surrounded by farmland, you'll enjoy watching the sun set off the back deck and be able to truly unwind in the private and peaceful setting.

Friday Harbour Ground Floor w/ Large Terrance

Welcome to FriYAY Getaways at The Friday Harbour Resort! Create unforgettable memories in our unique family-friendly condo. Beautifully designed, Two sets of cozy bunk beds, along w/a Queen bed & trundle.Accommodates 5-6 Adults 2-3 children. Each room is equipped w/a smart TV, offering access to Disney,Amazon Prime,& Netflix. Our backyard patio is perfect for entertaining, featuring a BBQ w/a pizza oven & griddle

Private Studio Apartment in Brampton on Airport Rd

Relax in the safe, beautiful, estate neighbourhood of Castlemore in Brampton, ON. Enjoy a fully private studio apartment located centrally off Airport Road with access to Toronto Pearson Airport in 15-20 minutes, Highway 410 in 5 minutes, Highway 427 in 10 minutes, and Downtown Toronto in 35 mins. Within reach to a number of grocery stores and fast food restaurants. One guest maximum due to studio size.