Cottage vacation rentals in Collingwood

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Top-rated cottage rentals in Collingwood

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Top guest favorite
A winterized cottage is surrounded by snow-covered terrain and tall trees. The exterior features large windows and a wraparound deck, offering views of the natural landscape. A black railing lines the deck, and a snow-dusted pathway leads to the entrance.
Cottage in Tiny
4.97 out of 5 average rating, 127 reviews

Cozy Winter Escape - Ski, Hike & Chill by the fire

Insta: @woodwardbythebeach 3min walk to the area’s most beautiful beach, sunsets & trails, you'll be sure to get lost in the serenity of the sand dunes year round Outdoor fire pit- s'mores included! Enjoy the BBQ, deck, & patio; the wine is on us! Fast WIFI for streaming movies or work from cottage Area is secluded yet central. 10min to Midland, close to Balm Beach - arcade, gokart, restaurant, & bar Ski/Hike/Snowmobile then unwind in a peaceful winterized home getaway with indoor fireplace

Top guest favorite
The two-storey beach house is illuminated at dusk, highlighting its stone exterior and expansive windows. Soft landscaping features are visible, with a gravel driveway leading to the entrance. Warm light emanates from inside, creating a cozy and welcoming ambiance.
Cottage in Wasaga Beach
4.98 out of 5 average rating, 111 reviews

Beautiful year round getaway for family & friends

This great 2-storey beach house is located beside a provincial park entrance with biking/walking trails. In summer enjoy the bars & shops of Beach Area 1. Kids love the Elmvale Zoo & Rounds Ranch - just minutes away. Blue Mountain offers excellent winter skiing, unique shops & restaurants. The more adventurous might explore the Scenic Caves of Collingwood or hanging bridge. Relax with family & friends at a crackling campfire or in the 7 person year round hot tub. Your mini vacation awaits.

Top guest favorite
A cozy corner features two checkered chairs positioned near a stone hearth. Natural light filters through a large window, highlighting the textured wall. A small table topped with a potted plant adds a touch of greenery, while the warm surroundings evoke a sense of comfort.
Cottage in Victoria Harbour
4.82 out of 5 average rating, 224 reviews

Serenity, Simplicity and Stone

This is a tiny cottage in a sleepy little hollow that opens onto the Georgian Bay. Inside, each stone was carefully chosen and the woodwork was built, piece by piece, by two craftsmen who are highly skilled and passionate about repurposing. It's an art that will leave you in awe; especially if you're worried about climate crisis. The coat hangers are upcycled 100-year-old railway spikes! If you're looking for luxury you will be disappointed but if you're a minimalist you're going to love it.

Top guest favorite
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, 260 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!

Top guest favorite
Cottage in Kimberley
4.91 out of 5 average rating, 346 reviews

Vintage School House ~Hiking, Skiing, Pet Friendly

Gather with family or friends in this vintage 5 bedroom School House in the Beaver Valley. -Ideal location to come together, relax, & connect. -Central heat & AC. -Take in the spectacular views of the Beaver Valley. -Explore the Niagara Escarpment and lookouts of the Bruce Trail. -Relax and read by the fireplace. -5 min walk to our swimming pond with dock & beach. -Convenient drive to groceries and local villages. -25 min drive to the Blue Mountains. -Reliable, consistent high speed internet.

Top guest favorite
A modern cottage features a stone exterior with a sloped roof, harmoniously blending into the surrounding forest. A cozy propane fireplace is visible on the patio, which overlooks a gently flowing stream bordered by smooth stones and lush greenery.
Cottage in Southgate
4.99 out of 5 average rating, 141 reviews

Luxurious Creek Retreat With Hot Tub

Welcome to this luxury cottage on the water. The perfect place to relax and unwind while listening to the waterfall and babbling brook flowing past only a few feet away. If you're looking for privacy and tranquility along with all the pleasures of a luxury stay then look no further. This property boasts a propane fireplace inside as well as one outside, in-floor heat and A/C. Fully equipped kitchen, two bedrooms with hotel quality mattresses and a bathroom that exudes high-end style and decor.

Guest favorite
A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.
Cottage in Tiny
4.96 out of 5 average rating, 139 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.

Guest favorite
A swimming pool is surrounded by a spacious patio, featuring lounge chairs for relaxation. The sleek water reflects sunlight, creating a serene atmosphere. Lush greenery and trees provide a natural backdrop, while a shed sits nearby, offering additional outdoor storage.
Cottage in Meaford
4.92 out of 5 average rating, 117 reviews

Woodski Retreat w/Heated Pool on 3+ Private Acres

This private mountain retreat is just 15 minutes from Blue Mountain, features 3.2 acres of beautiful scenery, a swimming pool and a renovated home for 10 guests (Max 8 adults). The house sits at the foot of a private 500ft mountain that is yours to explore all year around. Inside, there is a spacious home built for entertainment. Enjoy all-year fun at the property or head out to enjoy the amazing activities nearby. Only 5 minutes to the beach and 15 minutes to the best skiing in Ontario!

Guest favorite
An indoor hot tub is surrounded by wooden paneling and large windows that allow sunlight to fill the space. Natural stone accents and a serene greenery image on the wall enhance the calming atmosphere. Two wooden chairs are positioned nearby for relaxation.
Cottage in Kimberley
4.85 out of 5 average rating, 357 reviews

A Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi

30 minutes to Georgian Bay, 25 to Collingwood/Blue Mountain, and only 10 to Lake Eugenia's public beach. Our lovely, spacious, 5 Bed 5 bath retreat is nestled comfortably in the woods, convenient to almost every kind of activity and adventure. With 5 wash rooms and a large, INDOOR, jetted hot tub, it provides the perfect combination of convenience, relaxation, and outdoor adventure! BBQ, pool table, fireplace, fire pit, board games and high speed wifi. INSTA: @HIDDENHIDEOUTS

Guest favorite
A serene swimming pond is seen with calm, turquoise water reflecting the surrounding greenery. Bright red chairs are arranged on the sandy beach, offering a perfect spot for relaxation. Lush trees and a distant cottage provide a natural backdrop.
Cottage in Southgate
4.89 out of 5 average rating, 114 reviews

Thistle And Pine Cottage

Relax and unwind with the whole family at this peaceful place in the country. The cottage is on 50 acres that you have full access to. Great for swimming, walking, biking, cross country skiing, and much more. This 1 bedroom plus pullout couch(with privacy) is complete with kitchen, bathroom, and livingroom, and swimming pond with beach and Fire pit area that overlooks the pond. Perfect for a family of 4 or a romantic getaway for 2. Find us on Instagram @thistleandpine.cottage

Guest favorite
An inviting exterior of a single-story cottage is depicted, featuring a patio area with a table and chairs. A green umbrella provides shade, while landscaped garden beds and a pathway enhance the setting amidst lush greenery and a clear sky.
Cottage in Wasaga Beach
4.88 out of 5 average rating, 296 reviews

Cozy Riverfront Cottage Retreat with Dock / Ski

→Bright, 2 bedroom cottage with 1 queen, 1 twin bunk bed →Comfortably sleeps up to four →Fantastic views up and down the Nottawasaga River →Air conditioning, Firepit →9 Minutes to the NEW Wasaga Beach Casino →Great fishing (Steelhead, trout, pike, salmon, bass, pickerel), boating, canoeing, kayaking →Central to skiing - Blue Mountain, Mount St Louis Moonstone, Horseshoe →Large Dock on the Nottawasaga river →On-premise parking for up to 3 vehicles →High-Speed unlimited internet

Guest favorite
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
4.98 out of 5 average rating, 106 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.

Popular amenities for Collingwood cottage rentals

Quick stats about cottage rentals in Collingwood

  • Nightly prices starting at

    Collingwood vacation rentals start at € 138 per night before taxes and fees

  • Verified guest reviews

    Over 120 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Collingwood rentals

  • 4.8 Average rating

    Collingwood stays are highly rated by guests—averaging 4.8 out of 5!

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