Holiday houses in Simcoe County

RELAX @ our HOT TUB and SAUNA in the woods

PLEASE READ! Mt. St. Louis & Horseshoe Valley at doorstep! This is a bright, large and private walk-out GUEST SUITE (basement apartment). Hot tub, patio, fire pit & secluded path in the woods to enjoy nature. Kitchen is equipped with an induction cooktop and all things necessary, even wine bottle opener:) Open concept living room/kitchen/dining room with TV & Roku. Bedroom is a work of Art: dark, mysterious and romantic! Custom Queen bed made from weathered barn wood salvaged from our property.

Loft By The Bay

Welcome to our charming second storey apartment in downtown Midland, Ontario. This cozy space features a bedroom, office with futon, full kitchen, bathroom, laundry, and a bright open concept living area. Enjoy easy access to local shops, restaurants, and attractions. Explore the picturesque waterfront and nearby hiking trails. Retreat to this comfortable and inviting apartment after a day of work or play. Book your stay today for a convenient, comfortable, and memorable experience in Midland.

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.

Lakefront Cozy Cottage w Hot Tub!

On Lake Simcoe this cozy retreat is just an hour north of Toronto Enjoy the stunning sunrises / views and access to a variety of water activities, while the surrounding area provides ample opportunities for hiking, skiing, other outdoor pursuits with many amenities closely. Down the street from Friday Harbour, LCBO, Starbucks 5 star rating a must & ALL guests to be added to booking. Honey, our golden doodle will greet and visit with you. The cabin is to be left SAME as you found it.

Newly Built Woodsy Retreat - Your Perfect Escape

Woodsy Loft, an ideal home base for not just the beach and stunning sunsets, but Blue Mtn, Scandinave Spa, C-wood, brand new casino, all close by. Many bars, restaurants, beach and other things to do, within 5 min. Great place to stay in, too. Packed with amenities like screened in patio, XL bathtub w/ towel warmer, King size bed, 'The Frame' TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

King Bed, Pool, Gym, Ravine View, Your Getaway!

Enjoy a stylish experience in this spacious and serene space at Highland Estates Resort. You get a completely equipped designer suite that is perfect for couples sneaking away, or families looking for the perfect vacation. Enjoy a peaceful night in your private Jacuzzi then snuggle up in a King Bed. The next day, prepare your own meal in the fully equipped kitchen with Microwave and Electric Stove. Access Netflix, Prime, Disney+. Our Pool is Open! Book Us Today

Bright basement apt with private entrance, Barrie

Welcome to Your Bright Basement Retreat in Barrie! Our cozy and modern 2-bedroom basement apartment offers the perfect balance of comfort and privacy. Located in a quiet residential neighborhood, it’s ideal for couples, small families, or business travelers. With its own private entrance, high-speed Wi-Fi, a fully equipped kitchen, and convenient access to downtown Barrie and the GO Station, this apartment has everything you need for a comfortable stay.

Spacious Barrie Basement with Separate Entrance

This newly renovated 2-bedroom basement unit is bright and spacious, it offers a kitchenette, a bathroom, two bedrooms and laundry. Wifi/Bedding/Cookware/Bath Accessories/One Free Parking Spot on the driveway and free street parking (ONLY Available Apr-Nov). This is a great choice for your family summer/winter vacation! A few minutes' drive to downtown Barrie and beautiful Lake Simcoe waterfront, various restaurants, Costco, Walmart and unique shops.

Bluestone

Bluestone is located less than 10 minutes' drive from beautiful Awenda Provincial Park in Tiny, Ontario. Every choice was made with guest comfort in mind. In the Summertime, take a short walk down a wooded path to Georgian Bay and perfect swimming, or explore a hiking trail and take in the natural beauty of the area. In Winter, enjoy skiing and snowshoeing locally, or stay in, put a record on, and cozy up by the fire. Licence STRTT-2026-057

Private Basement Suite in a family neighborhood

Clean & spacious private Basement suite in a family neighborhood with all amenities that you may require for your stay. Features a queen bed, bathroom and kitchen. Free Parking is included. Highway 400, Park Place, Walmart, Costco, Canadian Tire are within 5-7 minutes driving distance. We offer our guests complete privacy from check-in to check-out, but always available if needed. Perfect for savvy budget travelers who deserve quality stay.

Glamping Dome Riverview Utopia

Come retreat into nature at the Riverview Glamping Dome… a 4 season getaway located on Rustic Roots Farm and Eco-retreat 1 hour north of Toronto. Whether you're looking for a romantic getaway or to come disconnect from the hustle and bustle of everyday life this geodesic dome is for you! Located on 64 sprawling acres come explore hiking trails, go fishing, relax in the hot tub, and stargaze fireside.

Boardwalk Bliss For Two *1 hr From TO!*

Waterfront Escape – 1 Hour from Toronto! Enjoy a private, street-level retreat steps from the marina boardwalk! Perfect for a relaxing getaway or remote work, with fast WiFi and in-room entertainment. 🌊 Activities Nearby: Waterside Dining & Boardwalk Music Nature Trails, Golf & Spa 🚤 Optional Add-Ons: ✔ Boating Excursions (Pre-Book) ✔ Dining & Activity Combos 📆 Book Now – Dates Fill Fast!