
Vacation rentals with a kayak in Grey Highlands
Find and book unique kayak rentals on Airbnb
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

Stunning Lakeside Loft Perched Above Georgian Bay
Architect-designed. Award-winning. Most unique property on The Bruce. Cozy, cool Lakeside Loft Guest House at Cameron Point. Open concept loft-style 2-storey Cabin and Bunky. Glass walls. Spectacular views of the water and bluffs! Summer: Loft + Bunky: 4 BR. Up to 8 guests from July 14. Extra fee for guests 5-8: $100/night pp Modern kitchen. 3-pce bath. Private entrance. Wifi. Winter: 2 BR. Base fee for up to 4 guests. Enjoy Bruce Trail hikes, swimming, kayaking. Chill by the fire!

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.

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

Cozy 'Off the Grid" Rustic Cabin
If you enjoy 'roughing it', stay in our beautiful log home from the late 1800's. It has been completely redone, maintaining all of the old character. It is nestled in the edge of the bush, that provides kilometres of hiking trails. The cabin is also situated on a pond so you can spend your days swimming, canoeing, fishing and exploring this nature lover's paradise. Spend your time here unplugging from your everyday life and reconnecting to the healing properties of a natural environment.

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.

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!

One bedroom apartment on the river, with hot tub
Keep it simple at this peaceful and centrally located place. 30 to 40 minutes to Port Elgin and Southampton, and 75 minute drive to Tobermory. The hot tub is always waiting. Full kitchen and bathroom available for your own use. New queen size bed replacing the queen sized pull out couch. In the warmer weather there is two kayaks and a canoe available for guests use plus four adult life jackets. Also close to Harrison park and the mill dam and you can go by river.

Boho Beaver Cabin 1 with saltwater hot tub
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. 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

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.
Popular amenities for Grey Highlands kayak rentals
House rentals with a kayak

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

Birdsong, the perfect Blue Mountains getaway

The Cedar House

Kiss & Bond Water View Colpoys Bay 4 -Seasons

Georgian Bay Waterfront Family Oasis

Algonquin sunrise on private balcony pond view

Serene Waterfront Escape On Private Lane

Eugenia escape
Cottage rentals with a kayak

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

Family Cottage On Quiet Lake w/ Shallow Entry

Charming 3bdrm cottage on Georgian Bay!

2 BEDRM WATERFRONT COTTAGE, CANOE, KAYAKS, WIFI

Waterfront Paradise on the Georgian Bay

The Bay View Cottage w/hot tub

Charming waterfront cottage on Lake Simcoe

Balmy Breezes - Waterfront Cottage with Hot Tub
Cabin rentals with a kayak

Waterfront Cottage on Severn Falls

Muskoka Haven, the Colonel's cottage

Muskoka Waterfront Cottage

The Blue Cottage

Deer Park, Cozy Cabin with Hot Tub, Amazing View

The Beach Deck Retreat

Cabin 10, Spacious Muskoka 2 Bedroom Cabin

Two - YES 2 cozy cabins !
When is the best time to visit Grey Highlands?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $216 CAD | $213 CAD | $216 CAD | $203 CAD | $254 CAD | $231 CAD | $233 CAD | $247 CAD | $220 CAD | $199 CAD | $197 CAD | $269 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 |
Quick stats about vacation rentals with a kayak in Grey Highlands

Total vacation rentals
Explore 60 vacation rentals in Grey Highlands

Nightly prices starting at
Grey Highlands vacation rentals start at $99 CAD per night before taxes and fees

Verified guest reviews
Over 2,220 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
30 properties have a dedicated workspace

Wifi availability
50 of Grey Highlands vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Grey Highlands rentals

4.8 Average rating
Grey Highlands stays are highly rated by guests—averaging 4.8 out of 5!
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- House rentals Grey Highlands
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- Blue Mountain Village
- Snow Valley Ski Resort
- Cobble Beach Golf Resort Community
- Beaver Valley Ski Club
- Devil's Glen Country Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- Mount St. Louis Moonstone
- TPC Toronto at Osprey Valley
- The Georgian Peaks Club
- The Club At Bond Head
- Caledon Country Club
- The Georgian Bay Club
- Barrie Country Club
- Alpine Ski Club
- Toronto Ski Club
- Mansfield Ski Club
- Legacy Ridge Golf Club
- Inglis Falls
- Heritage Hills Golf Club
- Springwater Golf Course
- Horseshoe Adventure Park
- National Pines Golf Club
- Shanty Bay Golf Club




