Beachfront holiday rentals in Grey Highlands

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Top-rated beachfront rentals in Grey Highlands

Guests agree: these beachfront homes are highly rated for location, cleanliness and more.

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Superhost
The image captures a tranquil hot tub filled with clear water, positioned on a deck overlooking Georgian Bay. A soft sunset casts a warm glow across the sky, and the silhouettes of a gazebo and dock are visible in the background.
Home in Meaford
4.87 out of 5 average rating, 495 reviews

Beach House Hideaway by Post Office Motel *HOT TUB

This beach house was designed with relaxation and the enjoyment of togetherness in mind. Let your worries melt away as you slip into the warmth of this water side hot tub featuring stunning view across Georgian Bay and up the mountain side, as fresh snow falls around you. The open concept design makes this the perfect place to gather with family and friends w/ walkout waterfront patio and dock access for swimming. 2 min to downtown Meaford, 20 min to Blue Mtn, 1.5 hrs to Tobermory. Hiking Trails

Top guest favourite
A spacious living area is highlighted by a large white stone fireplace, surrounded by comfortable seating. Natural light filters through sheer curtains, enhancing the warm atmosphere. A flat-screen television is mounted above the fireplace, and a wooden dining table sits elegantly in the foreground.
Cottage in Tiny
4.97 out of 5 average rating, 125 reviews

Summer Getaway - 3 min walk to Beach, Clean & Cozy

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
The exterior of the house is showcased with a large, angled roof and expansive glass windows reflecting the evening light. A spacious deck presents colorful chairs in pink and yellow, surrounded by sandy beach and foliage, enhancing the inviting outdoor space.
Flat in Wasaga Beach
4.95 out of 5 average rating, 419 reviews

2 bedroom beachfront apartment

Lovely suite with its own 3 piece bathroom, living room with flat screen TV and kitchenette. Has its own deck, barbecue and entranceway overlooking the sandy shores of Georgian Bay. Steps to go swimming, kayaking or a sunset stroll. Parking available. No pets. Between June 30th - September 1st the apartment can only be rented by the week (check in & check out on Saturdays only). Outside of these dates, we are happy to host visitors with a minimum 1 night stay, check in/out any day of the week.

Guest favourite
Cottage in Tiny
4.96 out of 5 average rating, 151 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.

Top guest favourite
Apartment in Innisfil
4.93 out of 5 average rating, 209 reviews

The Friday Flat | Sunny Escape by the Marina

Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake Come experience the ultimate waterfront getaway at Friday Harbour

Guest favourite
A serene sunset is captured over Georgian Bay, with warm orange and gold hues reflecting on the water. Silhouetted figures are seated on a dock, gazing out towards the horizon, creating a sense of tranquil evening ambiance.
Home in Victoria Harbour
4.84 out of 5 average rating, 151 reviews

Georgian Bay Paradise

Enjoy a relaxing vacation away from the hustle & bustle in this delightful 3 bedroom waterfront cottage. Just 90 minutes north of Toronto, this newly-renovated, gorgeous retreat is right on Georgian Bay, one of the world's most sought after destinations. Revel in breathtaking views, amazing sunsets and the privacy of numerous cedars. You will love the sun, sand, rock and waves which will captivate you. Access your own deck, lawn, and beach as well as many fun winter activities.

Superhost
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
4.89 out of 5 average rating, 122 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.

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, 150 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.

Top guest favourite
A peaceful dock stretches over calm waters, featuring two classic Adirondack chairs positioned to face serene natural surroundings. The still surface of the lake reflects the clear blue sky and lush greenery along the shore, creating a tranquil setting for relaxation.
Guest house in Gravenhurst
4.91 out of 5 average rating, 183 reviews

Waterfront Guest Cabin in Muskoka

Upscale guest cabin with brand new hot tub and WiFi deep in the heart of Muskoka. Unlimited access to a private hot tub, a dock with deep water diving, and a fireplace with night sky views. Remote cabin in nature with modern amenities and touches, accessible only by private road. Great for unplugging from social media and getting away from the city. Ideal for couples looking to relax, have campfires, and enjoy water activities such as swimming, kayaking, and paddle boating.

Top guest favourite
Two wooden Adirondack chairs are positioned on a lush green lawn facing the water, framed by overhanging tree branches. The sunset creates a colorful display on the horizon, reflecting on the calm surface of the lake, while a small table holds a wine bottle and glasses.
Guest house in Victoria Harbour
4.96 out of 5 average rating, 284 reviews

Sunset Beach Cottage

Part log treehouse, part beach house and 100% of what you need to enjoy a peaceful getaway only 1.5 hours from Toronto! Walk up the private staircase and pause to enjoy the spectacular treetop and waterfront views from your own wraparound deck before entering your 900 sq. ft. oasis. Enjoy access to your own lawn, picnic table and beach* area and all that Georgian Bay and the area has to offer. *water levels fluctuate Insta: sunset_beach_cottage_canada

Top guest favourite
Cottage in Georgina
4.91 out of 5 average rating, 290 reviews

Luxury Lakehouse Hot Tub Private Beach Lake Simcoe

Luxury Lake Simcoe Waterfront Retreat – 6BR/4BA lakehouse with private sandy beach, kayaks, SUP, lily pad, and hot tub under the stars. Cook in a lakeview open kitchen with floor-to-ceiling windows, or dine at the 14-seat solid wood table. Relax in 3 family rooms with fireplaces, a game room, and a new gazebo with outdoor sofas. Outdoors: lakeside firepit with Muskoka chairs, kids’ sand play area, west-facing sunsets, and space for family & group getaways.

Top guest favourite
A hot tub is positioned beneath a covered patio, offering views of the waterfront. The clear water of the hot tub contrasts with the lush green surroundings and the calm blue of the lake in the distance. Sunlight filters through the patio overhead.
Home in Port McNicoll
4.92 out of 5 average rating, 106 reviews

Breathtaking 5 bedroom Waterfront Home W/ Hot Tub!

Stunning five-bedroom waterfront home on Georgian Bay! Located in a quiet area with stunning views and amazing sunsets! In the summer, the lake is perfect for swimming, kayaking, paddle boarding or fishing! Just bring water shoes as there are some rocks and zebra muscles. Equipped with a hot tub overlooking the lake, this five-bedroom waterfront home is perfect for a summer or winter getaway! *Please note this cottage is Pet Free.

Popular amenities for beachfront rentals in Grey Highlands

Quick stats about beachfront rentals in Grey Highlands

  • Total holiday rentals

    Explore 20 holiday rentals in Grey Highlands

  • Nightly prices starting at

    Grey Highlands holiday rentals start at $64 SGD per night before taxes and fees

  • Verified guest reviews

    Over 770 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Grey Highlands holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi 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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