Cottage holiday rentals in Collingwood

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.

4.97 out of 5 average rating, 128 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

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.

4.98 out of 5 average rating, 115 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.

Cottage in Victoria Harbour

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.

4.82 out of 5 average rating, 228 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.

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.

4.94 out of 5 average rating, 266 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!

4.91 out of 5 average rating, 351 reviews

Cottage in Kimberley

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.

4.97 out of 5 average rating, 146 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.

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.

4.88 out of 5 average rating, 300 reviews

Cozy Riverfront Cottage with Dock

Escape to our cozy waterfront cottage on the Nottawasaga River in Wasaga Beach! This bright, airy retreat comfortably sleeps 4 and features a large private dock and fire pit both overlooking the river plus modern amenities, outdoor dining area and BBQ. Enjoy direct river access from the dock for fishing and boating. Perfectly located just minutes from the main Beach 1 and a short drive to Blue Mountain Ski Resort, Collingwood, Creemore and the Wasaga Casino. Your ideal getaway awaits!

4.85 out of 5 average rating, 360 reviews

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

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

An open kitchen features modern stainless steel appliances, including an oven and refrigerator. A large window allows natural light to fill the space, with a dining table set for four. Greenery in a vase adds a touch of nature to the countertop.

4.93 out of 5 average rating, 122 reviews

New and Cozy Cottage Minutes to Georgian Bay!

Conveniently located near the amenities, shops, and restaurants of downtown Meaford, our cozy stay is just steps from the Georgian Trail, a short walk from Georgian Bay, and a quick 20-minute drive from Blue Mountain Ski Resort. In Meaford and the surrounding areas, you'll find tons of local options to ski, bike, hike, swim, fish, golf and relax with family and friends. Embrace the Grey Highland's year-round beauty and enjoy the perfect blend of relaxation and outdoor excitement!

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.

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.

4.92 out of 5 average rating, 119 reviews

Woodski Winter Haven | Cozy Ski Stay + Hot Tub

Discover Woodski Mountain Retreat, a private winter escape minutes from Blue Mountain. Ski Ontario’s best hills by day, then unwind in the year-round hot tub under the stars. Enjoy a private 500ft mountain for sledding, cozy fireplace nights, open-concept living, and space for 10 (max 8 adults). The perfect blend of adventure and après-ski comfort. ✔ Hot Tub ✔ Ski-Ready Mudroom ✔ Fireplace + Smart TV ✔ Private Sledding Hill ✔ Minutes to Blue Mountain

A wooden dining area features a round table surrounded by four wooden chairs. The kitchen showcases wooden cabinets, a stove, a microwave, and a refrigerator. Natural light enters through a window above the sink, enhancing the warm wood tones of the room.

4.95 out of 5 average rating, 296 reviews

GATED RESORT COTTAGE

[CLICK SHOW MORE FOR IMPORTANT INFO] Sought-after cottage located in the gated Wasaga Country Life resort; professionally managed year-round by Parkbridge. A short walk from the beach with full access to resort amenities including; indoor/outdoor swimming pools, private trails, playgrounds, mini golf, sports fields and many more professionally managed facilities. View the "Where you'll be" section below for a full list of amenities.

Popular amenities for cottage rentals in Collingwood

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Superhost

A lakeside cottage is displayed from the dock, featuring a modern design with large windows and a spacious deck. The outdoor area includes a Jacuzzi surrounded by a stone border. Lush greenery frames the scene, enhancing the serene lakeside setting.

Cottage in Gilford

4.83 out of 5 average rating, 120 reviews

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

4.86 out of 5 average rating, 513 reviews

The exterior of a modern cottage is viewed, featuring natural wood accents and a blue siding. A spacious deck extends from the upper level, with tall windows allowing for ample natural light. Snow blankets the ground and evergreen trees frame the setting.

Cottage in Waubaushene

Charlie the Cottage | Hot Tub | Trail | Hike/Run

4.8 out of 5 average rating, 108 reviews

Cottage in Waubaushene

Georgian Bay Cottage-HotTub/Sauna/Swim/Hike/Marina

4.9 out of 5 average rating, 248 reviews

A large inflatable duck with headphones floats in a swimming pool, surrounded by evening lighting. A covered seating area features string lights, enhancing the tranquil and fun atmosphere. The backdrop includes a well-lit house surrounded by greenery, creating a relaxing outdoor space.

Cottage in Alcona

Utopia villa and spa

4.84 out of 5 average rating, 170 reviews

The cottage is situated on a well-maintained lawn, framed by trees, with a spacious deck accessible via a stone pathway. Colorful kayaks and a paddle boat are visible by the water, and the sky displays a warm sunset with varying shades of orange and purple.

Cottage in Waubaushene

Waterfront Paradise on the Georgian Bay

Large glass patio doors frame a scenic view of the waterfront, revealing a private deck with seating and a hot tub surrounded by trees. Sunlight casts a warm glow over the area, enhancing the sense of tranquility.

4.88 out of 5 average rating, 196 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

A spacious lake house exterior is set against a cloudy sky, featuring large windows that allow natural light to enter. The surrounding yard is adorned with fallen leaves, while a deck with outdoor furniture and a hot tub enhances the outdoor space.

4.87 out of 5 average rating, 148 reviews

Spacious family cottage 45 mins from GTA!

Cottage in Grey Highlands

A charming cottage exterior is surrounded by vibrant flower beds and lush greenery. The entrance features a set of stairs leading to a spacious deck, where colorful furniture is positioned. A garage with a dark door complements the inviting atmosphere of the property.

4.92 out of 5 average rating, 180 reviews

Hilltop garden cottage

Pet-friendly cottage rentals

5 out of 5 average rating, 67 reviews

A wooden deck extends over a calm pond, featuring two red Adirondack chairs and a matching bench. Lush greenery surrounds the water, with a windmill visible in the background under a clear blue sky.

Cottage in Flesherton

Greenery Lane - w/ private pond, hot tub & sauna!

A serene river reflects the vibrant colors of a sunset sky, with soft pink and orange hues blending with wispy clouds. Lush trees and calm waters create a peaceful ambiance, inviting relaxation and connection with nature.

4.98 out of 5 average rating, 86 reviews

Wasaga on the Water with Loads of Amenities

A modern living area is featured with a comfortable gray sofa facing a circular coffee table. Bright natural light fills the space, highlighting the white ceiling beams. A minimalist kitchen and dining bar with seating are visible in the background, creating an open layout.

4.92 out of 5 average rating, 62 reviews

A modern retreat on Georgian Bay STRTT-2026-089

The cottage exterior features a large wrap-around deck furnished with outdoor tables and umbrellas. Lush greenery surrounds the area, contributing to a peaceful atmosphere. A stone pathway leads to the entrance, and firewood is neatly stacked underneath the deck.

4.95 out of 5 average rating, 172 reviews

Cozy 4 Season Family Cottage

The exterior of a detached bungalow is illuminated by soft outdoor lighting. A gazebo provides shade over a patio with chairs and a table. Surrounding foliage displays autumn leaves, creating a tranquil ambiance.

4.8 out of 5 average rating, 69 reviews

Peaceful Cottage • Close to Lake Simcoe + Fire Pit

A modern kitchen is showcased with sleek white cabinetry and stainless steel appliances. A large island with bar seating is positioned centrally, complemented by stylish pendant lighting. The space is illuminated by recessed lighting and features a potted plant, contributing to a contemporary atmosphere.

4.91 out of 5 average rating, 138 reviews

Hot tub, Sauna, fire pit, close to Friday Harbour

The newly renovated cottage is surrounded by snow, featuring a welcoming front porch with white railing. Snow-covered steps lead up to the porch, framed by evergreen shrubs on either side. The sky displays vibrant hues of pink and blue at dusk.

4.88 out of 5 average rating, 49 reviews

Cozy Cottage w/ Hot Tub/GameRoom/Skiing/more!

4.99 out of 5 average rating, 117 reviews

A two-story cottage features a light gray exterior with a white railing surrounding a spacious balcony. A large, round umbrella provides shade over outdoor seating, while vibrant greenery and floral details adorn the front yard. A dark garage door is visible beneath the balcony.

Cottage in Alcona

❤️ Charming Cottage/Lake View/10PPL/5BDR/3BATH

Private cottage rentals

5 out of 5 average rating, 21 reviews

A comfortable living area features a large sectional sofa alongside a cozy armchair. Sunlight pours through multiple windows that provide views of the lake. A wood-burning stove and a coffee table sit centrally, with wooden walls enhancing the rustic ambiance.

Cottage in Flesherton

Lake Eugenia Renovated Waterfront Cottage

Superhost

A cozy kitchen area features a wooden dining table set for four, complete with plates and glasses. Large glass doors provide natural light and views of the outdoors. Kitchen appliances, including a refrigerator and a stove, are visible, alongside wooden accents and shelving.

Cottage in Singhampton

4.81 out of 5 average rating, 73 reviews

Serenity Cottage Getaway - Perfect for Families

A bright outdoor pool is surrounded by a spacious deck featuring lounge chairs in various colors. The water appears clear and inviting, while a shaded gazebo provides a relaxing spot nearby. Lush greenery is visible in the background, enhancing the outdoor space.

4.9 out of 5 average rating, 48 reviews

Wasaga Beach 1 BR basement -BBQ/POOL/AC

5 out of 5 average rating, 19 reviews

A blue hammock is suspended between two trees, offering a relaxed vantage point of the serene lake. In the background, a wooden deck features Adirondack chairs, inviting guests to take in the tranquil lake view surrounded by lush greenery.

Cottage in Flesherton

Lake Eugenia all season cottage

Cottage in Holland Centre

The exterior of the Riverfront Hideaway features a spacious home with a warm wooden facade and stone accents. A covered porch provides access to outdoor seating, while the expansive yard showcases areas for relaxation and enjoyment amid lush greenery.

5 out of 5 average rating, 78 reviews

Riverfront Hideaway*Hot Tub*Games Room*Firepit*BBQ

A charming cottage-style home showcases a combination of brick and wood features with a steeply pitched roof. The bright red front door is framed by lush greenery and well-maintained flower beds, enhancing the inviting entryway. A manicured lawn surrounds the home, creating a serene atmosphere.

4.98 out of 5 average rating, 65 reviews

The Gingerbread House | Near Lake + Wedding Venues

An inviting dining area features a natural wood table surrounded by woven chairs. A large pendant light with a straw finish hangs above the table, while soft curtains frame the windows, allowing natural light to fill the space. A cozy seating nook is visible in the corner.

4.98 out of 5 average rating, 49 reviews

The Hideaway Balm Beach Cottage

The stone cottage features a gabled roof and is surrounded by lush greenery and landscaped areas. Tall coniferous trees frame the entrance, while vibrant flowers add color to the exterior. Clear skies and open fields enhance the tranquil rural setting.