
Vacation rentals with a kayak in Grey Highlands
Find and book unique kayak rentals on Airbnb
Quick stats about vacation rentals with a kayak in Grey Highlands

Total vacation rentals
Explore 50 vacation rentals in Grey Highlands

Nightly prices starting at
Grey Highlands vacation rentals start at $111 CAD per night before taxes and fees

Verified guest reviews
Over 2,730 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Grey Highlands vacation 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 accommodations with a kayak in Grey Highlands
Guests agree: these accommodations with a kayak are highly rated for location, cleanliness, and more.

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

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.

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.

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.

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.

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.

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.

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

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!!!

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.

A Naturalist's Paradise - Shepard Lake waterfront
Located on a tranquil, private, inland lake-base of the Bruce Peninsula: Spacious suite (lower level of bungalow-one unit, no shared spaces), perfect getaway for outdoor enthusiasts. Private location with secluded sitting areas, firepit, yard & dock. Boats are exclusive for guest use. Enjoy fishing/bird watching. Fabulous hiking trails & beautiful beaches for swimming just minutes away. Close to golf courses. Relax on the dock, read, BBQ & enjoy campfires.

Modern Waterfront Home on Georgian Bay w/ Hot Tub!
Escape to a peaceful haven with this new and breathtaking modern waterfront cottage. Immerse yourself in the stunning views from the walkout deck with outdoor seating, a hot tub and a BBQ area. Quiet neighbourhood in Victoria Harbour on Georgian Bay. Short drive to charming town of Midland and nearby attractions such as the Tay Shore Trail and the Wye Marsh Wildlife Centre. This bright and beautifully finished home is less than a 2-hour drive from the GTA.
Popular amenities for Grey Highlands kayak rentals
House rentals with a kayak

The Sixth Great Lake Luxury

Welcoming Waterfront Cottage

The Lake House at Irish

Modern Country Getaway by the Bay

KickBack in Beautiful tranquil central condo

The Cedar House

Kiss & Bond Water View Colpoys Bay 4 -Seasons

Ski, Swim, Soak, Boat & Golf
Cottage rentals with a kayak

2 BEDRM WATERFRONT COTTAGE, CANOE, KAYAKS, WIFI

Waterfront Paradise on the Georgian Bay

Georgian Bay Waterfront Cottage HotTub King Bed

Balmy Breezes - Waterfront Cottage with Hot Tub

Forest Oasis in Tay w/Large Jacuzzi Hottub

Hot Tub & Sauna Retreat by Georgian Bay Trails

✦9Bedroom✦8400sqft Farm House ✦28Acres ✦1HrToronto

Forest Harbour Hideaway
Cabin rentals with a kayak

The Blue Cottage

Deer Park, Cozy Cabin with Hot Tub, Amazing View

Hawthorn Cottages - Bunkie #1

Lake view Blue cabin by the bay

Hawkson Cabin | Waterfront on Pearl Lake

Log Chalet | Private Lake+Games Room | 1hr Toronto

Two - YES 2 cozy cabins !

Skipping Rock Cabin: Cozy Charm & Hot Tub Bliss
When is the best time to visit Grey Highlands?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $252 CAD | $231 CAD | $253 CAD | $227 CAD | $214 CAD | $237 CAD | $230 CAD | $244 CAD | $217 CAD | $227 CAD | $235 CAD | $280 CAD |
| Avg. temp | -7 °C | -6 °C | -1 °C | 6 °C | 12 °C | 17 °C | 20 °C | 19 °C | 15 °C | 9 °C | 3 °C | -3 °C |
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- Blue Mountain Village
- Wasaga Beach Area
- Elora Gorge
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Beaver Valley Ski Club
- Awenda Provincial Park
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Scandinave Spa Blue Mountain
- Sauble Falls Provincial Park
- Elora Quarry Conservation Area
- Wye Marsh Wildlife Centre
- Mono Cliffs Provincial Park
- Centennial Beach
- Inglis Falls
- Harrison Park
- Cobble Beach Golf Resort Community
- Sunset Point Park
- Innisfil Beach Park
- Island Lake Conservation Area
- Sauble Beach
- Craigleith Provincial Park
- Guelph Lake Conservation Area





