Holiday rentals with a kayak in Grey Highlands

Find and book unique kayak rentals on Airbnb

Quick stats about holiday rentals with a kayak in Grey Highlands

Total holiday rentals
Explore 50 holiday rentals in Grey Highlands
Nightly prices starting at
Grey Highlands holiday rentals start at €70 per night before taxes and fees
Verified guest reviews
Over 2,730 verified reviews to help you choose
Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 30 rentals that welcome pets
Holiday rentals with a pool
10 properties feature pools
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 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!

Top-rated rentals with kayak in Grey Highlands

Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1

Top guest favourite

A charming A-frame cabin stands amidst tall grass, with the sun setting in the background. The metal roof glistens softly under the warm light, while large windows reflect the serene surroundings. Wildflowers can be seen in the foreground, adding natural beauty to the scene.

Guest house in Meaford

From A to Zen - a refined glamp

A unique tranquil getaway nestled on the Bruce Trail in the heart of the Niagara Escarpment. A short drive to Georgian Bay, Sauble, Blue Mntn, Scandinave Spa, Beaver Valley, Meaford theatre. A perfect midway for trips up the Bruce Peninsula. Better yet- stay put and unwind - sunrise coffee on the porch, kayak the river, bake a gourmet pizza, sunset in Muskoka chairs, stargaze from the hammock, a bonfire and dine in the open air at your very own table set for two - straight out of a storybook

4.97 out of 5 average rating, 100 reviews

Top guest favourite

Farm stay in Kimberley

Valley View Farm Retreat ~ Family, Pets, Hiking

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.

4.96 out of 5 average rating, 135 reviews

Top guest favourite

A well-maintained front yard features lush green grass, framed by trees. The entrance of the home is highlighted by a gray facade and a distinctive yellow accent above the doorway. Well-kept shrubs are positioned on either side of the path leading to the entrance.

Home in Wasaga Beach

Relaxing fall getaway / games room

Beautiful and charming home, 2 min walk to the beach, 20 min drive to Blue Mountain and Scandinave Spa. High speed WiFi, 3 TVs, spacious and elegantly decorated rooms perfect for families to connect. Central AC, 2 gas fireplaces. Fully equipped kitchen, fire pit, and gas BBQ. Games room with arcade games, pool table, basketball game, foosball table. Minutes to Canadian Tire, Walmart, LCBO, Tim Hortons, Starbucks and brand new Wasaga Beach casino, come relax and enjoy this amazing get away.

4.94 out of 5 average rating, 112 reviews

Superhost

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

This beautiful cottage of 2950sqft faces a breathtaking view of the Georgian Bay with over 105ft of lakefront. During the summer, this cottage is perfect for ATV and bike trails, wateractivities and fishing. The cottage includes kayaks and a paddle board for the guests to enjoy. During the winter, the cottage is ideal for ice fishing and is only a 13 minute drive to Mount St. Louis skiing. Under 10 minute driving distance to beaches, Tim Horton’s, LCBO, gas station, ice cream parlour and more.

4.84 out of 5 average rating, 191 reviews

Guest favourite

A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.

Cottage in Tiny

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.

4.96 out of 5 average rating, 182 reviews

Top guest favourite

A tranquil lakeside view displays a spacious cottage with large windows, reflecting on the calm water. Surrounding trees and a clear blue sky add to the serene atmosphere, inviting relaxation and enjoyment of the natural beauty.

Cottage in Georgian Bay

Muskoka Stunning Cottage On Little Lake

Surrounded by Little Lake, this gem provides a relaxing getaway with amazing water views. Spend your days peacefully rowing on the lake or having a picnic on the private beach, and your nights settling by a crackling fire. The home itself is plenty spacious for unwinding and getting a good night's sleep, views all-inclusive. Explore Port Severn Park right next door and play around in the public beach and splash pad. For more adventure, hike the beautiful Georgian Bay Islands National Park.

4.98 out of 5 average rating, 156 reviews

Top guest favourite

An open game room features a polished wooden pool table at its center, surrounded by exposed timber beams and vibrant green walls. Large windows provide natural light, while a television is mounted nearby. Additional seating is available, enhancing the space's social atmosphere.

Home in Meaford

Birdsong, the perfect Blue Mountains getaway

Welcome to Birdsong: a lavishly comfortable, highly unique, year-round space designed with an eye for the eclectic and enjoyable. This enchanting vacation property boasts an enormous hot tub that doubles as a heated indoor pool; as well as a sauna, well-equipped boutique gym, pool table, dedicated conference room/business center, outdoor fire pit and treehouse for kids. Surrounded by the gorgeous Blue Mountains, Birdsong is the perfect ski season rental; as well as summer family getaway.

4.98 out of 5 average rating, 118 reviews

Top guest favourite

The image captures a serene sunset over the water, with vibrant colors reflecting off the lake surface. Two trees silhouette against the backdrop, and gentle waves can be seen lapping at the shore, creating a tranquil atmosphere.

Cottage in Kemble

Georgian Bay Waterfront Oasis

Waterfront Cottage 15 mins north of Owen Sound on the crystal clear waters of Georgian Bay. We have 150 feet of private shoreline. Enjoy the east facing view and stunning sunrises, relax on a lounger, go for a swim, fish off the shore or in the small row boat, 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.

4.85 out of 5 average rating, 192 reviews

Top guest favourite

A communal outdoor space is presented, featuring wooden cabins with green roofs surrounded by tall trees. In the foreground, Adirondack chairs are arranged around a fire pit, with a hammock and a barbecue grill nearby, all set on a gravel surface.

Tiny home in Kimberley

Boho Beaver Cabin 1 with saltwater hot tub & sauna

So close, yet so far. Only 2 hours north of Toronto, 15 minutes to the base of Blue Mountain. This 108 square foot of "adorable" offers a four-season experience with a communal salt water hot tub and sauna. A river runs through it, the majestic Beaver River! This charming, boho inspired tiny cabin for two is nestled on an 80 acre property surrounded by farm fields, wildflowers, and ancient woodlands Check out our social media for more information and photos at: @BohoBeaver

4.99 out of 5 average rating, 153 reviews

Top guest favourite

A vintage boxcar exterior is framed by trees, with string lights adding a warm glow. A private hot tub situated nearby invites relaxation, while a barbecue grill is positioned on the patio. A light dusting of snow covers the ground, complementing the natural surroundings.

Tiny home in Utopia

Boho Vintage Box Car Utopia

Escape to a one-of-a-kind retreat in a beautifully renovated 2-bedroom vintage boxcar with a private hot tub. High speed internet available for entertainment or a work vacation. Located on Rustic Roots Farm & Eco-Retreat just 1 hr north of Toronto. Explore 64 acres of trails, relax by the spring-fed pond, enjoy bonfires, or fish along the winding Nottawasaga River. With organic gardens, wildlife, and birdwatching all around, it’s the perfect place to slow down and reconnect.

4.96 out of 5 average rating, 140 reviews

Top guest favourite

Cottage in Wiarton

Waterfront Cottage with Steam Sauna by Bruce Trail

Welcome to this stunning waterfront , cozy ,4 season cottage located on the edge of a cliff surrounded by the lake on one side and Bruce trail on the other. This private oasis is perfect for couples or families w. older kids where you can connect to nature but still stay close to the city. Walking distance to Bruce trail, short drive to Sauble Beach or Wiarton for shopping and dining, 25 min drive to Lions Head, 45 min to Tobermory. It's time to plan your visit to Bruce!!!

4.99 out of 5 average rating, 147 reviews

Top guest favourite

The log cabin is surrounded by vibrant autumn foliage, with a large front deck and stairs leading to the entrance. The natural wood exterior is complemented by a gabled roof. Softly illuminated lanterns are positioned by the door, enhancing the inviting appearance.

Cabin in Flesherton

MapleHaven Cabin @ Lake Eugenia

A rustically elegant log cabin sitting on an acre of beautiful mature maple trees on a quiet dead-end street. Find peace and tranquility in the rustic atmosphere the log cabin setting provides, but enjoy all of the comforts of home. Enjoy 3 bedrooms ,2 baths with a master bedroom that features a coffee bar and covered balcony . Located at Lake Eugenia, in the heart of the scenic Beaver Valley, a 4 seasons playground. Walking distance to public beach/boat launch.

4.96 out of 5 average rating, 129 reviews