
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 60 holiday rentals in Grey Highlands

Nightly prices starting at
Grey Highlands holiday rentals start at $65 SGD per night before taxes and fees

Verified guest reviews
Over 2,480 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
30 properties have a dedicated workspace

Wifi availability
50 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.

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.

Log Cabin on the Lake Bed and Breakfast
Log Cabin on the Lake Bed and Breakfast We provide a 1st morning continental breakfast A Lakefront getaway for couples with an amazing view. Experience tiny home living in a custom built Log Cabin. Landscaping provides privacy for all parties (owner next door) we have parking for a boat , with 2 launches within 5 min. One into Morrison Lake the other into the Trent Severn . cross country skiing, ice fishing, water skiing swimming boating. Ready to escape, our Log Cabin could be it.

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.

Upscale Spa Getaway w/ Private Sauna
Welcome to our most Dramatic & Romantic Penthouse Spa Getaway Suite! Reconnect with your loved one or celebrate that special milestone in our professionally designed to play with all your senses spa suite, this escape will leave you feeling refreshed and rejuvenated! Cozy up to any of 3 fire elements and then cleanse and detox in your own private in-suite Infrared Sauna! Cook up a gourmet meal in our fully equipped chef's dream kitchen and year round Weber BBQ for grilling!

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.

Beautiful Beachfront Cottage.
Township of Tiny License Number: STRTT-2026-110 Enjoy our all-season paradise only 1.5 hours north of Toronto! In summer, enjoy the sandy beach waterfront with incredible views of Georgian Bay with the Town of Penetanguishene, and all its historic charm, only 20 minutes away! In winter, enjoy all the area has to offer with incredible OFSC groomed snowmobile trails and amazing ski resorts less than an hour away! *Contract to be sent and signed prior to stay.

Lakefront Cottage | Sandy Shore, Hot Tub & Dock
Luxury lakefront cottage on beautiful Lake Simcoe with a rare shallow sandy-bottom waterfront, perfect for swimming and families. Relax in the hot tub and enjoy spectacular sunset views from the private dock. Ideal for family vacations and group getaways near Toronto, minutes from Hwy 404. Enjoy kayaking, paddleboarding, fishing, BBQ, a fire pit, 6 bedrooms, 4 bathrooms, a chef's kitchen, and bright open-concept living. Peaceful, private, and close to town.
Popular amenities for kayak rentals in Grey Highlands
House rentals with a kayak

River's End: Explore the river by kayak or canoe!

The Lake House at Irish

Modern Country Getaway by the Bay

The Cedar House

Ski, Swim, Soak, Boat & Golf

Kiss & Bond Water View Colpoys Bay 4 -Seasons

Georgian Bay Waterfront Family Oasis

Algonquin sunrise on private balcony pond view
Cottage rentals with a kayak

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

Private & Modern Muskoka Lakefront Cottage w/ WiFi

Cottage on the Rocks - with Hot Tub and Sauna!

Waterfront Paradise on the Georgian Bay

Georgian Bay Waterfront Oasis

Waterfront Cottage-Sauna, Dock, 4-bed, 4 Parking

Forest Harbour Hideaway

Tree Tops on Six Mile Lake
Cabin rentals with a kayak

Waterfront Cottage on Severn Falls

The Blue Cottage

Deer Park, Cozy Cabin with Hot Tub, Amazing View

Hawthorn Cottages - Bunkie #1

Two - YES 2 cozy cabins !

Skipping Rock Cabin: Cozy Charm & Hot Tub Bliss

Beautiful Vacation Home with a Large Backyard.

Beautiful Six Mile Lake Muskoka
When is the best time to visit Grey Highlands?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $234 SGD | $215 SGD | $235 SGD | $186 SGD | $233 SGD | $212 SGD | $213 SGD | $226 SGD | $202 SGD | $211 SGD | $218 SGD | $260 SGD |
| 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 |
Destinations to explore
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- Family-friendly rentals Grey Highlands
- Pet-friendly rentals Grey Highlands
- Rentals with a sauna Grey Highlands
- Guest house rentals Grey Highlands
- Rentals with a firepit Grey Highlands
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- Rentals with a hot tub Grey Highlands
- Beachfront rentals Grey Highlands
- Rentals with lake access Grey Highlands
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- Rentals with pools Grey Highlands
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- Rentals with breakfast Grey Highlands
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- House rentals Grey Highlands
- Rentals with a patio Grey Highlands
- Loft rentals Grey Highlands
- Rentals with a kayak Grey County
- Rentals with a kayak Ontario
- Rentals with a kayak Canada
- Blue Mountain Village
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Elora Gorge
- Beaver Valley Ski Club
- Wasaga Beach Area
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Awenda Provincial Park
- Scandinave Spa Blue Mountain
- Sauble Falls Provincial Park
- Cobble Beach Golf Resort Community
- Wye Marsh Wildlife Centre
- Centennial Beach
- Sauble Beach
- Mono Cliffs Provincial Park
- Inglis Falls
- Forks of the Credit Provincial Park
- Harrison Park
- Caledon Ski Club LTD
- Elora Quarry Conservation Area
- Sunset Point Park
- Innisfil Beach Park
- Island Lake Conservation Area





