Villa vacation rentals in Collingwood

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Top-rated villa rentals in Collingwood

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A bright landing area showcases sleek marble flooring and elegant light fixtures. Glass railings offer a modern touch, while a set of double doors leads to an outdoor space. Natural light filters through a nearby arched window, enhancing the welcoming feel of the upper level.

Villa in Port McNicoll

Luxury home, cozy, ski, snowmobile, hot tub, sauna

In the cusp of the Georgian bay, this large, detached house is custom & newly built, equipped with a heated sports pool (hot tub open all year), 5 bedrooms, Big screen TVs, IPTV, bar, laundry, high speed internet, kitchens, BBQ, fire pit, sauna, Foosball, bikes +more amenities & areas to entertain. Close to epic trails, beaches, lakes, and all of Georgian bay's features-close to stores. Perfect for families or small groups. Mature, respectful crowd, NO PARTIES, Covid++cleaning A+, pets ask :)

Top guest favorite

A circular above-ground pool is surrounded by a wooden deck. Sunlight reflects off the clear blue water, creating a serene atmosphere. A small shed is visible in the background, and potted plants provide a touch of greenery. Poolside chairs are arranged for relaxation.

Private room in Wasaga Beach

4.93 out of 5 average rating, 44 reviews

Fabulous vacation out of City

Fabulous spacious raise bungalow home, excellent location, country living & easy to commute to the City. Open concept, a lot of privacy. Shared space: family room with fireplace, exercise area ( few machines ). Private room and bathroom in the lower level. The room is equipped with: tv, a small fridge, coffee maker, mixer, microwave, iron,i.board, 2 pillows, blanket, 2 robes. 4 beach towels, shampoo, conditioner, soap. Parking available on the driveway, free parking permit within the city.

The great room features a large leather sectional sofa arranged around a wooden coffee table. Natural light fills the space through multiple windows, and a stylish area rug complements the modern design. The open concept leads to a kitchen area visible in the background.

Villa in Bradford West Gwillimbury

4.68 out of 5 average rating, 114 reviews

Executive Villa - Year Round Swim Spa & Game Room

Mediterranean inspired country villa: Get away from the big city and unwind in this luxurious custom built bungaloft - total 6000 Sq Ft livable space . Situated in an exclusive estate community enclave and sits on a private 2 acre property. The residence boasts a high-end kitchens, year round swim spa (outside) and game room (basement). Enjoy great shopping at nearby Tanger Outlet Mall. A short drive to Cooks Bay Marina, & only 20 minutes from Canada’s Wonderland & Snow Valley Ski resort.

Guest favorite

An aerial view captures the peaceful surroundings of the retreat, showcasing a green landscape with a winding canal leading to Lake Simcoe. The area features a mix of residential properties, trees, and a private dock, highlighting the abundant natural beauty and recreational opportunities.

Private room in Gilford

4.89 out of 5 average rating, 28 reviews

Lake Simcoe Retreat | Steps to Lake · Kayaks · BBQ

Discover your perfect 10-bedroom lakeside retreat on beautiful Lake Simcoe — ideal for family reunions, group getaways, or peaceful escapes. 🌿 In line with local township rules, we may list only up to three rooms for short-term rental. ✨ Planning a larger group stay? Reach out — we’re happy to help coordinate. ☀️ Summer fun awaits! Enjoy free kayaks, paddleboards, and pedal boats, or rent a motorboat nearby. ❄️ Winter adventures include ice fishing, skating, and snowmobiling nearby.

Superhost

A modern living area features a leather sectional sofa placed around a circular coffee table. A mounted television is displayed over a stone fireplace. Natural light is filtered through large windows, enhancing the open feel of the space, which includes a stylish accent chair.

Villa in Collingwood

4.79 out of 5 average rating, 112 reviews

The Family Escape Townhome

Conveniently located in Collingwood, Ontario only 1.5 hours from the GTA, this home is a 5 minute drive to Blue Mountain Resort, a 7 minute drive to Northwinds Beach & 20 minute drive to Wasaga Beach (the largest fresh water beach in the world!). Enjoy hiking/biking trails, golf and so much more! Set your day’s agenda from hitting the slopes, to relaxing at the spa. This home will make you feel warm and welcomed to the four-season destination of Collingwood & our neighbour Blue Mountain!

Guest favorite

A spacious living room features contemporary furnishings, including two sleek sofas arranged around a central coffee table. Tall ceilings and soft lighting highlight a large artistic photograph of trees. Neutral colors enhance the room's airy ambience, complemented by warm wood flooring.

Villa in Collingwood

5 out of 5 average rating, 9 reviews

Luxury Collingwood Getaway

Exquisite Custom Built Bungalow w/ 4 Beds, 4 baths & luxurious finishes throughout. ( 1 king, 1 queen, 1 double bed, 1 queen blowup set) Located in Collingwood, this stunning property has a balance of indoor and outdoor space. Unwind in the inviting hot tub, perfect for starlit evenings & soothing relaxation. This property offers a convenient proximity to Collingwood's finest amenities, hiking trails, & ski resorts are just a short drive away, ensuring year-round enjoyment.

A spacious outdoor area features a stone fire pit surrounded by colorful lawn chairs in pink and teal. The back of a two-story stone house is visible, with a balcony above overlooking the yard. Lush greenery and a wooden fence frame the scene.

Villa in Wasaga Beach

4.13 out of 5 average rating, 23 reviews

Beach1*com - Riverfront Resort - Villa #32

Located in the heart of Wasaga Beach on the Nottawasaga River, Beach1 Riverfront Resort has plenty to offer! Our resort features 3 separate stone crafted beach houses that can accommodate 15 guests each. It's a perfect place for large families & friends on vacation. Enjoy BBQs and bonfires with a riverside sunset and spectacular views. Being in the heart of Beach Area 1, you are right beside the events, attractions, and everything else the main end has to offer.

Three detached houses are visible, each featuring a balcony. Colorful chairs in pink and purple surround a bonfire pit on a sandy area. A Canadian flag stands nearby, gently fluttering in the breeze, with a clear blue sky and scattered clouds overhead.

Villa in Wasaga Beach

4 out of 5 average rating, 21 reviews

Beach1 Riverfront Resort - Villa #36

Located on the Nottawasaga River, in heart of Wasaga Beach, this beautiful, large waterfront property has plenty to offer! With three 2400 sq. ft. stone crafted detached houses, that can accommodate 17 guests each, it is a perfect place for multiple families or large groups on vacation. Being close to Beach Area 1, your walk to the main attractions on the beach and strip is very short. Enjoy BBQ's and bonfires with a riverside sunset!

Guest favorite

A sandy beach stretches out under a clear blue sky, with gentle waves lapping at the shore. A wooden pathway leads to the water, while a few people are seen walking along the beach, enjoying the serene coastal atmosphere.

Villa in Tiny

4.9 out of 5 average rating, 150 reviews

Beautiful Getaway Location - Cuddles Cove

Enjoy a all year round getaway either personal or corporate retreat at this spacious, well equipped Bungalow located short minutes walk from beautiful sand beach access. This newly built cottage is approx 5,000 Sqft with an additional 1,000 Sqft covered balcony offering accommodations of 6 queen beds, 1 Luxury full kitchen, 1 BBQ and lots of entertainment! Enjoy a nice Quiet getaway in the lovely community of Tiny! STRTT-2025-152

Superhost

A scenic landscape features a view of rolling hills covered in lush greenery under a blue sky dotted with clouds. A building with a red roof is partially visible, surrounded by vibrant trees and foliage.

Private room in Blue Mountains

4.99 out of 5 average rating, 168 reviews

Cardinals Roost Nature Retreat~2 Double Beds Room

If your looking to experience the quiet serenity of Nature, and leave the crowds behind for a peaceful romantic getaway, we are a 67 acre, upscale Bed & Breakfast, four season property, nestled hillside overlooking the stunning views of Pretty River Valley Provincial Park. ***Our Doubles room has 2 comfy double beds, a southern exposure nature view, and its own private ensuite with shower.

Superhost

The exterior of a spacious cottage presents a two-story structure with multiple windows allowing natural light. A large deck extends from the upper level, offering views of the surrounding landscape. The sandy area in front of the cottage leads to a rocky shoreline.

Villa in Tiny

4.87 out of 5 average rating, 67 reviews

The Sandals Of Tiny Hottub, Sauna, White SandBeach

Relax at this tranquil, newly refreshed 5-bedroom all-seasons cottage in Tiny Township on Georgian Bay. Escape the city and unwind with family and friends in the outdoor spa. Enjoy pristine beaches in the summer and ski slopes in the winter. Stay comfortable indoors with central AC, heating, a fireplace, and a big screen TV in the living room. No parties or events on premises.

Guest favorite

Villa in Tiny

4.98 out of 5 average rating, 100 reviews

Spacious Villa in Pines– Steps from Beaches!

Escape to this spacious and inviting home in Tiny, LaFontaine, just a short 3–4 minute walk from the stunning beaches of Georgian Bay. Designed for comfort and entertainment, our spacious home is ideal for families and groups looking to relax and create lasting memories, no matter the season.