
Vacation rentals with a kayak in Grey Highlands
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Top-rated kayak rentals in Grey Highlands
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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

Serenity by Georgian Bay, 4 Season, escape!
This charming, cozy house offers serenity edge of town, by Georgian Bay! Suitable for couples, families and small groups. Across the street from the Bay. Comes with kayak, SUP and lawn games! Close to many Bruce Trails, Scenic Caves trails, or Georgian Trail, and golf. After a busy day exploring or playing, retreat to Meaford and either whip up something delicious in our fully equipped kitchen and dine in with a view of the bay, or walk down Sykes 5 min to one of Meaford's excellent restaurants.

Valley View Farm Retreat ~ Hiking, Family, 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.

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.

Forest Harbour Hideaway
Situated on beautiful Georgian Bay, this cozy waterfront cottage delivers an escape from reality with all the comforts of home! With private access to the water and dock and our brand new custom sauna, and two public beaches within a 5 minute walk, unwind, relax and reset in the heart of our quiet cottage neighbourhood. Find a variety of shops, restaurants and local attractions in Midland and Orillia (both a 20 minute drive) like Sainte-Marie Among the Hurons and Wye Marsh Wildlife Centre!

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.

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!!!

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.

The Tiny House Experience
A unique experience awaits you in our cozy tiny house set back in the cedars. The lake is just steps from your front door where you can sit on the dock or canoe and kayak on the quiet inland lake. It is rustic tiny living, yet equipped with enough modern amenities to make your stay an enjoyable one. We welcome guests to bring friendly dogs and we expect that our guests will welcome the attention you will get from our dogs as well.

Breathtaking 5 bedroom Waterfront Home W/ Hot Tub!
Stunning five-bedroom waterfront home on Georgian Bay! Located in a quiet area with stunning views and amazing sunsets! In the summer, the lake is perfect for swimming, kayaking, paddle boarding or fishing! Just bring water shoes as there are some rocks and zebra muscles. Equipped with a hot tub overlooking the lake, this five-bedroom waterfront home is perfect for a summer or winter getaway! *Please note this cottage is Pet Free.
Popular amenities for Grey Highlands kayak rentals
House rentals with a kayak

The Sixth Great Lake Luxury

Welcoming Waterfront Cottage

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

The Lake House at Irish

The Cedar House

Ski, Swim, Soak, Boat & Golf

Georgian Bay Waterfront Family Oasis

Serene Waterfront Escape On Private Lane
Cottage rentals with a kayak

Georgian Bay Waterfront - Northwoods Lodge

Lake Eugenia Renovated Waterfront Cottage

Lake Eugenia all season cottage

2 BEDRM WATERFRONT COTTAGE, CANOE, KAYAKS, WIFI

Waterfront Paradise on the Georgian Bay

Balmy Breezes - Waterfront Cottage with Hot Tub

Hot Tub & Sauna Retreat by Georgian Bay Trails

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

Spectacular Georgian Bay Cottage

Cabin 12, a Cozy 3 Bedroom Muskoka Cabin

Hawthorn Cottages - Bunkie #1

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

Two - YES 2 cozy cabins !

The White Cottage with infinity views

Skipping Rock Cabin: Cozy Charm & Hot Tub Bliss

Bring Everyone to Georgian Bay
When is the best time to visit Grey Highlands?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$37,791 GYD | G$34,659 GYD | G$38,000 GYD | G$30,066 GYD | G$37,582 GYD | G$34,242 GYD | G$34,451 GYD | G$36,539 GYD | G$32,571 GYD | G$34,033 GYD | G$35,286 GYD | G$41,967 GYD |
| 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 G$10,440 GYD per night before taxes and fees

Verified guest reviews
Over 2,480 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & 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

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





