Holiday houses in Glencairn

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Top-rated holiday rentals in Glencairn

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

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Guest favourite

Home in Mulmur

4.81 out of 5 average rating, 32 reviews

Mulmur Hills Victorian Farmhouse

Virginia’s Heritage Farmhouse: Nestled in the Mulmur Hills region of the Niagara Escarpment, this beautiful century farmhouse provides an exceptional countryside retreat experience for guests looking for a breath of fresh air and an opportunity to see the stars at night. Surrounded by county forests, guests will enjoy peace and quiet at this geographically unique and picturesque farmstead. Convenient proximity to Orangeville, Shelburne, Alliston, Barrie, Collingwood, Creemore & Wasaga Beach

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Top Guest favourite

A private wooden deck is shown with an umbrella-covered table and four chairs, surrounded by lush greenery. Windows on the building's façade allow natural light, while potted plants add a touch of color, enhancing the outdoor space for relaxation.

Apartment in Horning's Mills

4.96 out of 5 average rating, 344 reviews

Beautiful Riverside Country Apartment

Bright, warm and newly renovated, this 900sqft apartment, a private floor of a charming country home with separate entrance and garden patio, awaits you in Melancthon. SmartHDTV, Wifi, tranquil surroundings, and the Bruce Trail. Close to Shelburne, Mansfield, Creemore, Pine River Institue and many excellent restaurants (The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

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Guest favourite

A spacious glamping dome is nestled among lush green trees, showcasing large windows and a triangular design. The entrance is framed by rustic outdoor seating, and soft lighting emanates from inside, creating an inviting atmosphere amidst the surrounding foliage.

Dome in Utopia

4.95 out of 5 average rating, 284 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.

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Guest favourite

A circular stone fire pit is surrounded by wooden Adirondack chairs, offering a cozy gathering space. A vibrant fire burns in the center, with lush greenery and a serene riverside view in the background under a colorful sky.

Cottage in Wasaga Beach

4.94 out of 5 average rating, 298 reviews

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!

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Top Guest favourite

Farm stay in Stayner

5.0 out of 5 average rating, 31 reviews

Doc Ives Farmhouse

Modern farmhouse near Creemore on 120 acres with beautiful views of Georgian Bay, farm land, pastures and cows. Master bedroom on main level and 3 bedrooms with king beds. An arboretum with 100 species of trees. Hot tub and sauna overlooking the rolling fields. Very private with a back lane for romantic walks. Newly updated interior with 2 pianos, pool table, library and a bright new kitchen perfect for welcoming your friends. 15 minutes from Wasaga Beach and 25 minutes from Blue Mountain.

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Top Guest favourite

An open-concept living room and kitchen area is highlighted by a cozy gas fireplace and a cathedral ceiling. Light-colored walls complement the stylish green cabinetry. Two barstools are positioned at the kitchen island, with natural light streaming through the window.

Apartment in Nottawa

5.0 out of 5 average rating, 118 reviews

The Nottawa Nest

Spacious loft apartment, nestled in the heart of Nottawa, a quiet and friendly village just 5min. south of downtown Collingwood and 15min. from Blue Mountain and Wasaga Beach. Enjoy next door the local pub restaurant, cafe, bookstore & LCBO variety store. This beautifully finished getaway has two comfortable bedrooms, laundry room with daybed, dedicated work space, open concept living room & kitchen with cathedral ceiling & gas fireplace. Perfect for two couples, small family or group.

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Top Guest favourite

Home in Grey Highlands

4.98 out of 5 average rating, 57 reviews

Rosewood Parlour A-Frame by The Post Office Motel

Where treehouse dreams grew up, got a glow-up, and ordered champagne. Perched in the treetops on the escarpment’s edge, this A-Frame proves the best kind of luxury is a little wild. The primary suite shower and stone soaker tub deliver panoramic views of the valley. Every bedroom offers stunning views. Soak in the hot tub under a glittering blanket of stars, sweat it out in the sauna with views so good they deserve a toast. Cozy, chic, and a little extra—because basic was never the plan!

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Top Guest favourite

The exterior of a modern home is highlighted at sunset, showcasing large windows that reflect warm interior lighting. A spacious backyard features green grass, a dining area under a gazebo, and a hot tub on the deck, creating an inviting outdoor space.

Home in Barrie

4.97 out of 5 average rating, 158 reviews

Waterfront Home, City/Sunset View & Steps to Beach

Waterfront w/ private dock. Renovated upscale home + new hot tub, full city bay views w/summer sunsets+sunrise. Steps to Minet's Point beach & park. 4 proper bdrms & 2 pull out couches(Queen & Twin) 3 full bthrms + sauna, over 2400+sqft. Prking for 3 cars, additnal prking available via lot beside. Gas BBQ, fire pit, 2x gas FP, fast Wifi & 77" TV, wshr/dryr. 48amp EV pwr. Minutes to Marina for Seadoo/boat rentals. Wlking distnce to fine dining/pubs & stores. Kite surf & ice fishing

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Guest favourite

Home in Stayner

4.9 out of 5 average rating, 20 reviews

Blue Mountain Retreat • Michelin Dining

⭐ Top 1% rated Luxury woodland retreat near Blue Mountain, Collingwood and Wasaga Beach Relax in a thoughtfully designed space with cozy fireplace, plush bedding, and hotel-style comfort throughout. Quiet small town setting—just minutes to skiing, hiking, and scenic Georgian Bay escapes. Ideally located just 10 minutes from The Pine in Creemore—one of Ontario’s most sought-after Michelin-recognized dining experiences—making this the perfect stay for a refined weekend escape.

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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

5.0 out of 5 average rating, 411 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.

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Luxe

The striking facade of the modern lake house is framed by lush greenery, showcasing large windows and a unique architectural design. A custom pickleball court is visible in the foreground, bordered by flower planters, enhancing the outdoor environment.

Cottage in Meaford

4.96 out of 5 average rating, 132 reviews

Bayview Oasis: Luxe Lakeside Escape w/ Pickleball

Welcome to Bayview Oasis, our luxurious lake house on Georgian Bay. Enjoy breathtaking water views, a modern kitchen with high-end appliances, a cozy basement with a pool table and bar, and a master suite with top-notch amenities. Outdoors, relax in the cabana with a pizza oven, fireplace, picnic tables, spacious patio, hot tub, and our new custom pickleball court. Whether it's a romantic getaway or family vacation, Bayview Oasis is the perfect retreat.

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Top Guest favourite

A covered outdoor seating area features white wicker furniture with turquoise cushions. A small brown table sits in the center, surrounded by lush green foliage, creating a serene and intimate space for relaxation. Light curtains flutter gently in the breeze.

Cabin in Mulmur

4.98 out of 5 average rating, 57 reviews

Private Log Cabin with 7 Queens 2 futons + hot tub

Forget your worries and enjoy the beautiful nature and the variety of wildlife in this spacious and serene space. Enjoy the outdoor shower on hot summer days. taking in the amazing night skies, perfect for star gazing in or out of the hot tub. Creemore and its brewery are close by, we're not far from Wasaga Beach or Blue Mountain and Collingwood so there's something for everyone and all seasons.

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