Cabin holiday rentals in Simcoe County

Lakefront getaway for two on Musselman's Lake

An amazing getaway space for two and your dog on beautiful Musselman's Lake, close to Toronto but feels like you're in the Muskokas. This rustic designer one-bedroom cabin is the original attached cottage that our house grew from. Sit at the dock or on your patio to watch the spectacular sunsets. Have a coffee in the backyard and watch the sunrise over 160 acres of trails out your back door. This is your retreat with high-speed internet, full-size kitchen & dining area to enjoy cottage life.

🍺"Happy Daze"-Big Space, Near Village+Lots of fun

Legendary Tyrolean Village Chalet. Just 1 km from Blue Mountain lifts! Perfect for ski trips/golf & year round group getaways. Enjoy 36+ trails, private hot tub, fire pits, Smart TVs, Wi‑Fi, BBQ, and mountain-view decks. Lots of close by beaches, ropes courses, Collingwood Harbour, and Scandinavian Spa. Tyrolean Lane is known for fun, festive vibes—ideal for big crews looking to après-ski, celebrate, & make memories! This area is becoming such a year round destination that summer is bustling!

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

Mill Pond Cabin, Nordic Cabin w/ Sauna + Hot-tub

Welcome to your next weekend retreat, or work from home during the week in a private nature focused environment with amazing wellness amenities. From the cedar Sauna and hot tub, game corner and indoor gas fireplace- we have your relaxation and entertainment covered. Host your dream dinner party with our gas range stove, pellet smoker and BBQ to choose from. You'll be sounded by cedar forest on all sides on our private road, just 1hr N-E of downtown TO. Ideal for groups of 2-3 couples

Hockley Valley Cozy Cottage

Take it easy at this unique and tranquil setting where the entire property is yours! Freshly renovated cottage only 600M from Hockley Valley Resort and also close to restaurants and hiking trails. This cottage sleeps 4 comfortably with separate bedroom. Picturesque setting directly on Nottawasaga river with mature gardens and plenty of outdoor space. Morning coffee or afternoon drinks under the covered gazebo at the waters edge or relax in the hammocks, this place truly has it all.

Romantic Cabin N the Woods just 80km from CN Tower

This Romantic 1 bedroom Rustic Cabin was resurrected from the original homestead to re-invent this Cabin just for Couples! Birthdays, Anniversaries, Honeymoons & Proposals! Sleep under 2 -4’ huge Skylights watching the moon as it crosses directly overhead in the Loft Bedroom! Or simply enjoy a time away to re-connect with your loved one! Sit under stars Year Round in the modern new Hot tub after your run or walk on 200 acres of hilly trails 5kms from the cabin ( Brown Hill Tract)

Cozy Cottage Bed and Breakfast. Set on 4 acres.

Set on 4 acres of wooded land, this wee Bed and Breakfast provides a relaxing country retreat. Basic breakfast provided. High speed WIFI on site !! My one bedroom B&B is complimented by a deck with BBQ and fire pit. It is a 3 min walk to the Bruce Trail and 5 to Noisy River Provincial Park. Located on county Rd 9 and ideal for biking, hiking and sleeping. The Noisy River is a fav spot hiking. Downhill & xskiing are close by. Creemore & Beer 7 minutes.

Private Romantic Cabin with Hot Tub

Are you seeking a romantic getaway nestled in the serene beauty of nature? Look no further than our secluded cabin in the forest, providing complete privacy, and a rustic charm. You’ll find everything you need to relax & unwind. At Alive Wilderness Retreat we believe that the natural beauty of the forest provides the perfect backdrop for creating lasting memories.

Reay Lake Tiny House

Take it easy at this unique and tranquil getaway. Reay Lake is conveniently located just 10 minutes to Gravenhurst. This 700 Sq ft cabin is situated on an acre and a half property for ultimate privacy. There is an access point for kayaks provided just 90 meters from the driveway.