Guesthouse vacation rentals in Simcoe County

Cabin in the forest with Snowshoeing included

Relax and unwind at this peaceful and private Guesthouse situated on 25 acres of forest. We are family friendly and invite you to roam the land and visit our ducks and chickens! If you are feeling adventurous, enjoy a hike or bike ride on one of the many local trails within walking distance in the Trail Capital of Canada! Later cozy up to the indoor Woodstove or outdoor Firepit. Catch up on your fav programs w/Roku TV or play Super Nintendo. Enjoy the newly renovated therapeutic rainfall shower.

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

Mono Countryside Home & Farm

If you’re looking for a quiet place to get away, Mono Countryside Home and Farm is the place for you. This charming guest home in Mono, is set back from the road and surrounded by towering pines with lots of room to roam in the forest and nearby Mono Cliffs Provincial Park. This open concept guest home with stunning views includes a warm fireplace, full kitchen and high speed internet. Complimentary biscotti and fresh farm eggs + you can order Italian cuisine from your host at Connie's Kitchen.

Brookside Cottage - Charming Rural Getaway Mulmur

Our cozy guest house, situated in the Headwaters region, has it all! Close to hiking,golfing,biking,skiing. XCski/snowshoe from your door! Big skies for astronomers and astrophotography! We offer 32 acres of forest and fields for walking and taking in the magnificent views. The area boasts fine restaurants, boutiques, markets and artisans. Minutes to Mono Cliffs, Boyne, Mansfield Ski Club and easy driving to Blue Mountain and Wasaga Beach. Ideal for couples, solo adventurers or a small family.

Serene Comfort. Hot Tub, Full Suite with Kitchen

Welcome to Centre Street Studio! Our 600 sq/ft bachelor suite offers a private, clean and cozy retreat. Enjoy access to a private 2 person hot tub and/or explore our local trail system. Beautiful Scandinavia Spa or Vetta Nordic Spa, both within 40-min. Barrie, Creemore, & Wasaga Beach are all within 30-mins, while Collingwood & Blue Mountain are just 40 min. A 2-min drive to town amenities. NOTE: We don't host guests new to AirBNB or who have no previous reviews attached to their profile.

Hillside Studio | Midland + Southern Georgian Bay

Welcome to the Hillside Studio — a bright and spacious 900 sq. ft. private guesthouse in the heart of Midland. Perched on a hillside, this modern one-bedroom retreat is designed for comfort, light, and relaxation for 1–2 guests. Perfectly located for exploring Georgian Bay: • 10-minute walk to Downtown and Little Lake Park • 15 minutes to Wye Marsh Wildlife Centre and Sainte-Marie among the Hurons • 20 minutes to Awenda Provincial Park • 30 minutes to Vettä Nordic Spa/Quayle’s Brewery

Warnica Coach House

Welcome to the Warnica Coach House! This unique and historic property will not disappoint! Built by George R. Warnica in 1900, this spectacular property was the recipient of the Heritage Barrie award in 2018. The Coach House where you will stay, once housed horses and carriages, has been completely renovated top to bottom in 2023 with the finest touches. We are centrally located with a 30 second drive from the 400, and an 8 minute walk to the waterfront, restaurants, and downtown fun.

Exclusive Cabin Retreat | King Bed | Pet Friendly

Tucked away on our family farm, this cabin is exclusively yours and offers a peaceful countryside escape. Enjoy farm views, a king bed, full kitchen, gazebo covered propane BBQ , and cozy evenings in the country. Blinds on every window let you create your own quiet retreat indoors, while the property itself is shared with our family farmhouse, our Country Suite (attached to our farmhouse), and our Event Barn in the distance. Perfect for couples, small families, or dog-friendly getaways.

Chalet w/ yard & pool, walk to beach & playground

Barrie's most comfortable and friendly chalet, with a rustic ambience that has had a documentary filmed in it! Warm and luxurious with A/C, gas fireplace and gourmet kitchen, with park. beach and playground on Lake Simcoe a two minute walk away. A welcoming, fully equipped home away from home for families, couples, friends and travellers in a beautiful, mature neighbourhood featuring nearby walking and biking trails. For longer stays we are happy to offer discounts, just inquire!

The Hideout | Garden Suite & Backyard Grill

Welcome to The Hideout – Your Cozy Garden Escape 🌿✨ The Hideout is a stylish one-bedroom, one-bathroom garden suite designed for comfort and relaxation. Thoughtfully decorated in calming blue and warm brown tones, with elegant gold accents, this inviting retreat blends modern sophistication with a warm, homey atmosphere. Whether you’re here for a weekend getaway or a short stay, The Hideout is perfectly situated just minutes from Barrie’s downtown, waterfront, and local attractions.

Bright & Cozy 2BR Retreat Near Downtown and Nature

Welcome to a cozy, quiet 2-bedroom retreat designed for comfort and easy living. Enjoy a peaceful space with warm furnishings, comfortable beds, and a fully equipped kitchen—perfect after a day downtown, on nearby forest trails, or commuting for work or hospital visits. Minutes from downtown with quick highway access, free parking, and a calm neighbourhood, this home is ideal for couples, small families, and professionals year-round. This flat is not wheelchair accessible.

Waterfront Guest Cabin in Muskoka

Upscale guest cabin with brand new hot tub and WiFi deep in the heart of Muskoka. Unlimited access to a private hot tub, a dock with deep water diving, and a fireplace with night sky views. Remote cabin in nature with modern amenities and touches, accessible only by private road. Great for unplugging from social media and getting away from the city. Ideal for couples looking to relax, have campfires, and enjoy water activities such as swimming, kayaking, and paddle boating.