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Holiday houses in Simcoe County

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Top-rated holiday rentals in Simcoe County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.
Dome in Bradford West Gwillimbury
4.96 out of 5 average rating, 461 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Top Guest favourite
Guesthouse in Orangeville
4.96 out of 5 average rating, 381 reviews

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.

Top Guest favourite
The historic Beck House, a striking Victorian structure, stands with a distinctive red façade and slate roof. A spacious porch with white railings invites guests, while the well-kept lawn adds to its charm. A wooden sign identifies the property, blending history with a warm welcome.
Apartment in Penetanguishene
4.89 out of 5 average rating, 528 reviews

The Haunted House Apt 302

As you pull into the driveway this 1885 Victorian towers above you, your mouth drops in awe of the size. Up the porch to enter a small front door, a dimly lit winding staircase creaks as you ascend to 3rd floor. Original architecture painted many times over oozes with history. 70 years ago the house was turned into apartments, unloved for many of those years, time has definately taken its tole, yet to the spirits within, their big old house still stands proud and distinguished in all its glory.

Guest favourite
Dome in Utopia
4.95 out of 5 average rating, 265 reviews

Off-grid Glamping Dome Nestled in the Woods

Welcome to our private campsite in Utopia, ON. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (summer only), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation Area, Nottawasaga & golf courses. Wasaga Beach is 30 min away.

Guest favourite
Cottage in Tiny
4.96 out of 5 average rating, 151 reviews

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

Top Guest favourite
The open-concept living area features a comfortable sofa set against wooden accents and a rustic coffee table. The kitchen is visible in the background, equipped with modern appliances. Large windows allow natural light to fill the space, complementing the warm tones of the wood flooring.
Guesthouse in Barrie
5 out of 5 average rating, 255 reviews

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.

Top Guest favourite
Farm stay in Uxbridge
4.98 out of 5 average rating, 305 reviews

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

Welcome to the LOFT - A private, eclectically designed spa-inspired unique stay in the historic Webb Schoolhouse, less than an hour from Toronto. Featured in TORONTO LIFE, this private loft includes a sauna, unique hanging bed, wood stove, kitchenette and is filled with art, and huge tropical plants as well as a projector & giant screen for epic movie nights. Relax and recharge, roam the grounds and enjoy the beautiful outdoor spaces, the permaculture farm, animals, and fire pit.

Top Guest favourite
The spacious bedroom features a king-sized bed adorned with decorative pillows, complemented by a wooden bedside tray. An armchair occupies one corner, with a desk and paddles adorning the wall. Floor-to-ceiling windows illuminate the room, while exposed wooden accents add a rustic touch.
Apartment in Wasaga Beach
4.95 out of 5 average rating, 489 reviews

The Upper Deck

The upper deck is an amazing one bedroom studio with a full newly renovated bathroom, a sweet kitchenette, an amazing king size bed, a 65 “ inch HD smart Samsung TV with a live edge counter- a great workspace or eating area. One wall is floor to ceiling windows -lots of great natural light!!! Outdoors has an amazing hot tub , rustic firepit area , a beautiful covered outdoor eating area with Bbq and you can hear the lake!! Note- the studio is a separate but is part of a house.

Guest favourite
The charming exterior of the bunkie features rustic wooden siding and three large windows. A welcoming front porch is furnished with two chairs and a small table, surrounded by a natural landscape of trees and open space, showcasing the tranquility of the setting.
Tiny home in Coldwater
4.82 out of 5 average rating, 103 reviews

Bunkie On The River

Welcome to our four season bunkie retreat on the river. Leave the world behind and seek comfort and peace at Riverside Ranch. Imagine starting your day reconnecting with nature amidst wooded walking trails. Along your walk you see geese swimming in the river, goats exploring the woods, and Highland cattle grazing in the pasture. Upon return, you open the door to the crackle & pop of a toasty wood burning sauna, followed by an icy cold plunge in the river. *No air-conditioning*

Top Guest favourite
A modern bathroom features a freestanding soaking tub situated next to a window, allowing natural light to fill the space. The vanity displays a mirror and toiletries. Nearby, a spacious bed with soft linens is visible, set against a backdrop of wooden walls.
Place to stay in Wasaga Beach
4.99 out of 5 average rating, 378 reviews

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.

Superhost
The geodesic dome features a modern white exterior, set against a backdrop of trees. A wooden deck extends from the dome, leading to a covered gazebo, with a pathway of wood chips guiding the approach. Soft sunlight filters through the branches, creating a serene atmosphere.
Dome in Uxbridge
4.84 out of 5 average rating, 99 reviews

The Bubble Glamping Dome

Escape to a luxury geodesic dome on our scenic farm, nestled at the edge of the forest. Fully equipped with heating, cooling, a private washroom, deck, and hot tub, it’s the perfect blend of comfort and nature. Explore the farm, meet our sheep, chickens, and livestock guardian dog, or hike over 100 acres of connected regional forest. Whether you’re relaxing under the stars or adventuring outdoors, this unique glamping retreat promises an unforgettable experience.

Guest favourite
A relaxing outdoor space features a circular fire pit surrounded by four red Adirondack chairs. A stack of firewood sits nearby. Behind the seating area, a glimmering glass geodesic dome is surrounded by lush greenery and open sky.
Dome in Zephyr
4.95 out of 5 average rating, 162 reviews

Glass Dome - Sleep Under The Stars- Free Sundays

Discover this new, stunning 22ft Glass Geodesic Dome nestled in the heart of Uxbridge. Imagine waking up surrounded by 360-degree panoramic views of the natural landscape Please note... its FULL WEEKEND STAYS ONLY - BOOK FRIDAY AND SATURDAY-SUNDAY IS FREE. This allows guests to fully enjoy their Sunday without feeling rushed to check out at 11am. Enjoy all day Sunday with option of staying the evening. 8X12 BUNKIE NOW AVAIL. SLEEPS 4 ( 2 bunk beds)

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