Cottage holiday rentals in Simcoe County

Summer Getaway - 3 min walk to Beach, Clean & Cozy

Insta: @woodwardbythebeach 3min walk to the area’s most beautiful beach, sunsets & trails, you'll be sure to get lost in the serenity of the sand dunes year round Outdoor fire pit- s'mores included! Enjoy the BBQ, deck, & patio; the wine is on us! Fast WIFI for streaming movies or work from cottage Area is secluded yet central. 10min to Midland, close to Balm Beach - arcade, gokart, restaurant, & bar Ski/Hike/Snowmobile then unwind in a peaceful winterized home getaway with indoor fireplace

CARL in Muskoka: Waterfront Cottage with Hot Tub

Enjoy your own piece of Muskoka in this beautiful waterfront cottage! Only 90 minutes from Toronto nestled away on a private road along the Severn River sits CARL. Not a man... but a way of life. The Cottage and River Life! CARL is your retreat from the city, perfect for getting out in nature and experiencing everything life on the water has to offer. Whether you enjoy swimming, kayaking, great fishing or just relaxing on the dock or in the hot tub taking in the views... we've got you covered.

Utopia villa and spa

Welcome to Utopia B&B, a peaceful retreat where lasting memories are created with family and friends. Just minutes from the beach, grocery stores, gas stations, and all everyday essentials. With so much to enjoy, you may never want to leave! Spend your day savoring good food by the fireplace, relaxing in the hot tub, unwinding in the sauna, and having fun in the game room. Indulge yourself with an unforgettable stay. : No smoking or eating in the hot tub. Any violation will result $500 fine.

Luxury Lakefront Cottage | Hot Tub & Sunset Views

Private lakefront cottage on Lake Simcoe with hot tub, sunset views, and a rare shallow sandy-bottom waterfront — a unique feature that’s hard to find. Ideal for large family and group getaways near Toronto, just a short drive from Hwy 404. Enjoy swimming, kayaking, paddleboarding, BBQ, firepit, private dock, fishing, and lakeside fun. Spacious 6 bedrooms, 4 bathrooms, a chef’s kitchen, and open-concept living make it perfect for relaxing and gathering. Close to town, yet private and peaceful.

Charming riverside cottage, B&B license

Charming riverside cottage available on Wasaga Beach. Just a 4-minute stroll from a pristine sand beach. Immerse yourself in nature's beauty while enjoying modern amenities, including a private hot tub for relaxation. Unwind with a friendly round of mini-golf or gather around the fire pit for cozy evenings under the stars.Create lasting memories at this perfect oasis that combines riverside tranquility, mini-golf fun, hot tub relaxation, and the warmth of a fire pit. Your dream getaway awaits!

The Squire's Cottage

Welcome to Fairview Hills Farm. Relax on the spacious covered porch of The Squire’s Cottage watching horses grazing on the hillside. A short walk to the back of the property features natural wetlands with an abundance of different bird species. The Bruce Trail is close by with parking. Don’t feel like cooking? An assortment of restaurants, high end to take out, are close by or cook up a storm in the fully equipped kitchen. In the evening cozy up with a good book in front of the fireplace.

Resort-Style Luxury Waterfront Cottage

Experience luxury at our 5-star, Superhost-rated waterfront cottage on Lake Simcoe, just 80 KM from Toronto! A guest favorite, it offers breathtaking sunsets and sunrises from the living room and loft. Relax on the sandy beach with waist-deep waters, and enjoy the patio, BBQ, bar, lounge, kayaking, and fishing. With a fully equipped kitchen, 3 bedrooms, and 2 bathrooms, it comfortably accommodates up to 8 guests. Book your dream getaway today for the perfect blend of relaxation and adventure!

Relax at The Rock: Muskoka Waterfront Cottage

Enjoy fishing, swimming and paddling 22km of the green and black rivers. Paddleboat, canoe, 2 kayaks, and a SUP provided. Take the short 5 minute stroll into town for ice cream or fresh baked treats. Lay out on the elevated deck or in the screened in porch with a good book. End your evening at the riverfront firepit. Nearby day adventures include hiking, golfing, parks, beaches, breweries, casino rama, and downhill skiing at Mount St Louis Moonstone and Horseshoe Valley (30 minute drive).

Cozy Riverfront Cottage with Dock

Escape to our cozy waterfront cottage on the Nottawasaga River in Wasaga Beach! This bright, airy retreat comfortably sleeps 4 and features a large private dock and fire pit both overlooking the river plus modern amenities, outdoor dining area and BBQ. Enjoy direct river access from the dock for fishing and boating. Perfectly located just minutes from the main Beach 1 and a short drive to Blue Mountain Ski Resort, Collingwood, Creemore and the Wasaga Casino. Your ideal getaway awaits!

Charming Waterfront Cottage - Muskoka - 4 seasons

Welcome to the Cottage on Reay Lake! This 4 season house is your perfect tranquil escape. Located in the Muskoka's, our waterfront home is only 2 hours away from the Greater Toronto Area. The cottage was built in 2009 and hosts open concept living with 3 bedrooms & 2 full bathrooms. Amenities Include, Starlink Wifi, Lakefront, Canoe, Paddle board, Kayak, Life jackets, BBQ, Firepit, Laundry, Mountain Biking, nearby Golf, & a Drive-in theatre. Reconnect with nature; relax and unwind…

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Modern 4 season waterfront cottage! Stunning views! Located on picturesque Nine Mile Lake. Over 70% of the lake is crown land. Perfect for kayaking and canoeing to enjoy all the beauty Muskoka is known for. We have kayaks a canoe and a paddle board for you to enjoy. Plenty of sun exposure on the dock you can swim all day long. Close to hiking and snowmobile trails. May 15-Oct Minimum 6 nights with a Sunday check in.

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

Our lakeside home in Cook’s Bay offers 4 bedrooms, 2 bathrooms, and is just an hour from the GTA—perfect for a peaceful getaway. You may spot local wildlife like geese or ducks around the lake and docks, but they won’t block access. The property is pet-friendly; please clean up after your dogs and prevent them from entering neighboring properties. *Note:per city regulations, the dock is removed from mid-October to mid-May.