Cottage holiday rentals in Collingwood

4.99 out of 5 average rating, 141 reviews

An aerial view of a cottage located on a waterfront lot is showcased, framed by lush greenery. A large deck and seating areas are visible, along with a hot tub and sauna. Several boats are docked at the waterfront, indicating access to water activities.

Cottage in Alcona

Charming waterfront cottage on Lake Simcoe

Charming 4 bedroom cottage plus Boat house conveniently located 1 hour from GTA on a private waterfront lot surrounded by mature trees sandy bottom clear water. Proximity of the cottage to the water is sure to please either the sun or shade lovers with multiple large decks dock for sitting dining and lounging. We offer hot tub Sauna basketball net paddle boat floating mat kayaks canoe paddle board pool table, foosball. fishing gear, life jackets. Summertime is by the week, Saturday to Saturday.

The exterior of a modern cottage is framed by tall trees and colorful foliage. A spacious deck wraps around the cottage, providing outdoor seating options. The gravel pathway leads to the entrance, surrounded by natural landscaping and decorative stones.

4.97 out of 5 average rating, 126 reviews

Fall Escape - dazzling colours & stunning beach

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

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, 217 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, 258 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, 343 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.

4.99 out of 5 average rating, 135 reviews

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

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.

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.

4.92 out of 5 average rating, 116 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!

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, 111 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 exterior of Sanablue features a vibrant yellow facade with blue accents, complemented by a stone pathway and lush greenery. Inside, a cozy living area is highlighted by a colorful artwork and a smart TV, creating an inviting space for relaxation.

4.95 out of 5 average rating, 181 reviews

Sanablue - Stylishly Un-Trendy since 1958!

Sanablue is a quiet & warm out of the way escape for your family ... that's right next to everything that's great about South Georgian Bay! See reviews for our track record! Just 91 barefoot steps to the edge of Georgian Bay IF YOU DARE!. A 4 min stroll to grab a coffee (or a bottle of wine). Just meters to Oakview Woods hiking trails & Wasaga biking trails. 10 min to Collingwood. 15 min to breathtaking Blue Mountain ..... Or just put your feet up & relax.

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, 293 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.

An aerial view captures a waterfront community at sunset, featuring modern buildings along the marina. Boats are docked at the waterfront, and a serene lake reflects the warm colors of the sky. Lush greenery lines the horizon, adding a sense of tranquility.

4.88 out of 5 average rating, 329 reviews

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!

A wooden deck surrounds a cozy cabin, featuring a shaded barbecue area and two hot tubs. Colorful flower pots add vibrancy, while a large red umbrella provides shade. Lush greenery surrounds the space, enhancing the outdoor setting.

4.96 out of 5 average rating, 262 reviews

Private 40 Acre Cottage with Hot Tub

Our two bedroom cabin + cubby (available in summers) by a scenic pond is a private getaway while close to the main road and many amenities. Private outdoor space includes hot tub, deck, fire pit, and walking trails. We have a barn with ping pong and foosball tables. We are 20 min to Barrie, 10 min to Midland, 20 min to Balm beach, Wasaga beach, Mt. St Louis and Horseshoe Valley resort.

Popular amenities for cottage rentals in Collingwood

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.85 out of 5 average rating, 354 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

A charming cottage is seen surrounded by trees, with a large deck above. A fire pit is centrally located in the grassy yard, circled by several wooden chairs. A kayak rests nearby, hinting at outdoor activities, while the serene natural setting offers a peaceful retreat.

4.85 out of 5 average rating, 500 reviews

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

4.9 out of 5 average rating, 239 reviews

A loft area features a wooden railing adorned with greenery, providing a cozy viewing spot. A circular wooden table is accompanied by two matching folding chairs, inviting relaxation. Warm lighting enhances the natural wood tones of the ceiling and walls, creating a welcoming ambiance.

Cottage in Alcona

Utopia villa and spa

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.

4.84 out of 5 average rating, 166 reviews

Waterfront Paradise on the Georgian Bay

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, 146 reviews

Spacious family cottage 45 mins from GTA!

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, 189 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

4.91 out of 5 average rating, 110 reviews

Red Adirondack chairs are positioned on the dock, overlooking a sandy beach area and a lake. The cottage is visible in the background, surrounded by trees, with colorful kayaks resting on the shoreline. A welcoming atmosphere is created by the spacious outdoor setting.

Cottage in Flesherton

Sunset Cottage on Lake Eugenia -Hot Tub-4 Seasons

An aerial view captures a spacious outdoor deck surrounded by tall trees. Seating under a striped umbrella is visible on the deck. A winding stone path leads to a landscaped area featuring vibrant green plants and seating arranged in a circle, inviting relaxation.

4.95 out of 5 average rating, 105 reviews

Lafontaine Beach Rustic Chalet- New HOT TUB.

Pet-friendly cottage rentals

Cottage in Blue Mountain Resort Area

A two-story house is framed by a snowy landscape, with a sloped roof and multiple windows reflecting the daylight. A car is parked in the driveway, which is bordered by trees and a surrounding wooden fence. The scene conveys a serene winter setting.

4.85 out of 5 average rating, 20 reviews

Blue Cottage Five minutes walk to ski lift

5 out of 5 average rating, 65 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, 59 reviews

A modern retreat on Georgian Bay STRTT-2025-062

A sandy dune is shown, with tufts of grass growing from its surface. The dune rises against a backdrop of scattered clouds and a clear blue sky, representing the natural landscape near the beach.

4.94 out of 5 average rating, 80 reviews

The Beach House Licence#: STRTT-2024-028

A spacious cottage is set among lush green trees, providing a serene and inviting entrance. The exterior features a warm brown facade with multiple windows, framed by vibrant foliage that enhances the natural ambiance.

4.8 out of 5 average rating, 106 reviews

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

A serene view of Georgian Bay is framed by the branches of a tree. A wooden dock extends into the calm water, with a gentle shimmer reflecting sunlight. A grassy area, bordered by a stone wall and a nearby building, complements the tranquil outdoor setting.

4.95 out of 5 average rating, 59 reviews

Charming 3bdrm cottage on Georgian Bay!

A dining table is elegantly set with floral-themed plates and utensils, surrounded by glasses in varying colors. A spacious hot tub is visible nearby, encased in a wooden deck, with greenery creating a private ambiance. A vibrant sign adds a pop of color to the scene.

4.75 out of 5 average rating, 539 reviews

The Surf Shack - Hot Tub, Bay Views & Beach Access

Private cottage rentals

4.81 out of 5 average rating, 70 reviews

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

Serenity Cottage Getaway - Perfect for Families

5 out of 5 average rating, 20 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

A spacious living area is illuminated by natural light from large windows. A green sofa is positioned next to a coffee table on a soft area rug. The open layout includes a dining area with a bench and modern decor, creating a welcoming environment.

4.99 out of 5 average rating, 67 reviews

Edmore Cottage at Tiny Beaches

4.87 out of 5 average rating, 70 reviews

A rustic log home is nestled among tall trees, approached by a dirt driveway lined with grass. The warm exterior of the home is complemented by a blue sky and scattered clouds, indicating a serene setting in the woods.

Cottage in Berkeley

Fortress of Solitude

A sandy beach area is visible under a twilight sky, with gentle waves lapping at the shoreline. In the background, a well-lit cottage and a rustic bunkie stand amongst sparse trees, creating a serene lakeside atmosphere.

4.72 out of 5 average rating, 46 reviews

Georgian Bay Getaway - Lakehouse

A spacious living area features a cozy sectional sofa and a round coffee table, centered around a decorative area rug. A modern fireplace offers warmth, while large windows provide ample natural light. A flat-screen television is mounted above the fireplace, enhancing the entertainment space.

4.71 out of 5 average rating, 59 reviews

Blue Mountain Ski Chalet | Wasaga Beach Retreat

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, 58 reviews

The Gingerbread House | Near Lake + Wedding Venues

A charming two-story home features natural wood siding with a welcoming front porch. Two wicker chairs are set on the porch, complemented by decorative planters. Lush greenery surrounds the property, enhancing the inviting atmosphere.