Waterfront holiday rentals in Grey Highlands

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Top-rated waterfront accommodation in Grey Highlands

Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

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Top Guest favourite
A cozy seating area features two rattan swivel chairs with a view of Georgian Bay through large windows. The hardwood floor is complemented by a small round side table, while a potted plant adds a touch of greenery to the inviting space.
Apartment in Meaford
4.96 out of 5 average rating, 441 reviews

Sunrise and Bayview with Kayaks & Bikes

🌊 Bright and inviting waterfront/view ground level apartment in the heart of Meaford. 👋Entire apartment to yourself 👥Ideal for a romantic getaway 🏔20 minute drive to Blue Mountain attractions. 2 hours from Bruce Peninsula National Park 🏖 5 minute stroll to the Harbour and Sandy Beach or a pebble beach right across the road ! 🚶‍♂️Walking distance to Meaford Hall 🍽Dining options a block away:) Kayaks, Bikes, Floaties, snowshoes and snorkels are complimentary. Come and discover our gem of a town

Top Guest favourite
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 favourite
Farm stay in Kimberley
4.95 out of 5 average rating, 98 reviews

Valley View Farm Retreat ~ Hiking, Skiing, Pets

Enjoy this unique 4 bedroom Farm House as a gorgeous space to gather with family or friends. -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 favourite
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, 143 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.

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, 314 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 next to the Bruce Trail. Close to Shelburne, Mansfield, Creemore, and many excellent restaurants (like The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, and Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

Guest favourite
Cottage in Tiny
4.96 out of 5 average rating, 141 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 favourite
A serene waterfront scene captures a vibrant sunrise over the calm waters of Georgian Bay. Silhouettes of trees frame the image, while soft waves reflect hues of orange and yellow in the sky. The shoreline is visible, enhancing the tranquil atmosphere.
Guesthouse in Kemble
4.86 out of 5 average rating, 199 reviews

Waterfront Sunrise Cottage

Private waterfront cottage 15 mins north of Owen Sound on the crystal clear waters of Georgian Bay. With a 150 feet of shoreline shared only with a neighbouring cottage, enjoy the stunning sunrises, relax on a lounger, go for a swim, kayak, paddle board, go fishing or have a camp fire and stargaze. Use our cottage as a jumping off point for many hikes along the Bruce Trail, Sauble Beach (35min), Tobermory (70min) and many more. Or just work from here while enjoying the great view and wifi.

Top Guest favourite
Chalet in Meaford
4.98 out of 5 average rating, 103 reviews

Sundance of Blantyre Ski Lodge w/ Hot Tub & Sauna

Welcome to Sundance of Blantyre! Step back in time in this historic yet modernized Lodge! This 3600 sq. ft retreat on the Bruce Trail has Breathtaking Valley Views from your own Private Hot Tub & Fire Pit all the Way to Georgian Bay. We invite you to enjoy our truly unique and tranquil getaway with 6 bedrooms + Private Sauna House! With 3 firepits, swimmable/fishing pond, hiking, cross country skiing and snow shoeing + snowmobile/ ATV trail access at your door, Your adventure awaits!

Top Guest favourite
A spacious living area is equipped with a large sectional sofa and a rounded ottoman. A flat-screen television is mounted on the wall, while a mirror reflects natural light from the sliding glass doors leading to an outdoor patio. Plants are arranged to enhance the decor.
Cabin in Orangeville
4.97 out of 5 average rating, 186 reviews

Hockley Valley Cozy Cottage

Take it easy at this unique and tranquil setting where the entire property is yours! Freshly renovated cottage only 600M from Hockley Valley Resort and also close to restaurants and hiking trails. This cottage sleeps 4 comfortably with separate bedroom. Picturesque setting directly on Nottawasaga river with mature gardens and plenty of outdoor space. Morning coffee or afternoon drinks under the covered gazebo at the waters edge or relax in the hammocks, this place truly has it all.

Guest favourite
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
4.91 out of 5 average rating, 115 reviews

Sunset Cottage on Lake Eugenia -Hot Tub-4 Seasons

Well maintained/clean family lake front 4-bedroom cottage with sandy beach entry & 5" off the dock. We offer a large living room with a wood burning fireplace, dining room with full lake views, open kitchen, finished basement rec room with queen pull-out couch and laundry. Access to acres of privately owned forest land great for hiking, mountain biking, ATV’s, snowshoeing, close to the bruce trail, waterfalls and abundant nature. Our ideal guests are families with or without kids.

Guest favourite
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

Top Guest favourite
A two-story cottage is set beneath a large tree with autumn-colored leaves. The exterior features a mix of large windows and a white railing leading up to an entrance, surrounded by grass and shrubbery.
Cottage in Flesherton
4.95 out of 5 average rating, 148 reviews

All-Season Cottage on the Lake

An entire cottage all to yourself right on the water of Lake Eugenia in the Grey Highlands. This fully furnished 3-bedroom cottage is equipped with a brand-new kitchen, appliances, wood burning stove, furnace and water heater. You'll also have FREE access to unlimited WiFi, so you can work or stay in touch, when needed. Our cottage is suitable for a great get-away with any group, family or friends who are looking for a peaceful and enjoyable holiday from their busy lives.

Popular amenities for Grey Highlands waterfront rentals

When is the best time to visit Grey Highlands?

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Avg. price$222 AUD$228 AUD$218 AUD$225 AUD$260 AUD$286 AUD$300 AUD$324 AUD$281 AUD$227 AUD$225 AUD$272 AUD
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Quick stats about waterfront rentals in Grey Highlands

  • Total holiday rentals

    Explore 100 holiday rentals in Grey Highlands

  • Nightly prices starting at

    Grey Highlands holiday rentals start at $75 AUD per night before taxes and fees

  • Verified guest reviews

    Over 3,070 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 50 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Grey Highlands holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Grey Highlands rentals

  • 4.9 Average rating

    Grey Highlands stays are highly rated by guests—averaging 4.9 out of 5!

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