
Holiday rentals with a kayak in Grey Highlands
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Top-rated Accommodation with a Kayak in Grey Highlands
Guests agree: these holiday homes 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

Fire & Ice Spa w/ Private Sauna!
Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

Valley View Farm Retreat ~ Hiking, Skiing, Pets
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.

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.

"Blue Vue" Georgian Bay Waterfront Cottage
1933 Original cottage on the beautiful clear waters of Georgian Bay just northwest of Meaford, this area offers some of the best swimming, cycling, hiking, fishing and exploring in cottage country. Our private property offers 120 feet of sandy beach with gradual slope into the water and beautiful underwater sandbars right out in front. Situated on a narrow private lane way, this cottage is close enough to town for convenient shopping yet is nestled into a friendly rural cottage community.

One bedroom apartment on the river, with hot tub
WINTER SPECIAL 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.

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.

Birdsong, the perfect Blue Mountains getaway
Welcome to Birdsong: a lavishly comfortable, highly unique, year-round space designed with an eye to 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.

The Bay View Cottage w/hot tub
Welcome to our 4 season, 2 family cottage with Georgian Bay views and a hot tub. 3 min walk to the cutest small beach that has stunning sunsets, 12 min to Awenda Provincial Park which has great hiking, beaches, biking and winter activities. Short drive to Balm Beach. Downtown Midland has great restaurants and everything a quaint downtown has to offer. Winter has so much to offer including ice fishing, OFSC snowmobile trails, cross country skiing and much more. Max occupancy is 8 adult.

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.

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.
Popular amenities for Grey Highlands kayak rentals
Holiday House Rentals with a Kayak

The Sixth Great Lake Luxury

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

Modern Country Getaway by the Bay

Muskoka Cottage on the Severn River

The Cedar House

Waterfront cottage in Elmvale, Orr Lake

168 Fairway to Ski View Retreat

Beaver Valley Farmhouse with Pool & Stunning Views
Cottages with a kayak

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

Lake Eugenia Renovated Waterfront Cottage

Family Cottage On Quiet Lake w/ Shallow Entry

2 BEDRM WATERFRONT COTTAGE, CANOE, KAYAKS, WIFI

Waterfront Paradise on the Georgian Bay

Spacious family cottage 45 mins from GTA!

Georgian Bay with Hot Tub & Sauna, on Tay Trail !

✦9Bedroom✦8400sqft Farm House ✦28Acres ✦1HrToronto
Cabin rentals with a kayak

Waterfront Cottage on Severn Falls

Muskoka Haven, the Colonel's cottage

The Blue Cottage

The Beach Deck Retreat

Hawthorn Cottages - Bunkie #1

Two - YES 2 cozy cabins !

Skipping Rock Cabin: Ski, Soak & Warm Up

Beautiful Six Mile Lake Muskoka
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 AUD | $214 AUD | $216 AUD | $204 AUD | $255 AUD | $232 AUD | $233 AUD | $248 AUD | $221 AUD | $231 AUD | $239 AUD | $284 AUD |
| 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 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 $85 AUD per night before taxes and fees

Verified guest reviews
Over 2,510 verified reviews to help you choose

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

Pet-friendly accommodation
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

Wi-Fi availability
50 of Grey Highlands holiday rentals include Wi-Fi 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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- Rentals with a patio Grey Highlands
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- Blue Mountain Village
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Beaver Valley Ski Club
- Wasaga Beach Area
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Scandinave Spa Blue Mountain
- Elora Gorge
- Caledon Ski Club LTD
- Harrison Park
- Inglis Falls
- Elora Quarry Conservation Area
- Forks of the Credit Provincial Park
- Innisfil Beach Park
- Mono Cliffs Provincial Park
- Sauble Beach
- Awenda Provincial Park
- Wye Marsh Wildlife Centre
- Centennial Beach
- Sauble Falls Provincial Park
- Sunset Point Park
- Island Lake Conservation Area
- Rockwood Conservation Area




