
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

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.

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.

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.

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.

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

Georgian Bay Waterfront - Northwoods Lodge

Welcoming Waterfront Cottage

Peaks in The Happy Valley

The Cedar House

Georgian Bay Vibes, Relax and Reset in Meaford

Sunsets on the beach

Serene Waterfront Escape On Private Lane

Beaver Valley Farmhouse with Pool & Stunning Views
Cottage rentals with a kayak

Cottage on the Rocks - with Hot Tub and Sauna!

Lake Eugenia all season cottage

Waterfront Paradise on the Georgian Bay

2 BEDRM WATERFRONT COTTAGE, CANOE, KAYAKS, WIFI

The Bay View Cottage w/hot tub

Balmy Breezes - Waterfront Cottage with Hot Tub

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

Forest Harbour Hideaway
Cabin rentals with a kayak

Spectacular Georgian Bay Cottage

The Blue Cottage

Deer Park, Cozy Cabin with Hot Tub, Amazing View

The Beach Deck Retreat

Hawthorn Cottages - Bunkie #1

Beautiful Log Chalet with Private Lake

Two - YES 2 cozy cabins !

Skipping Rock Cabin: Ski, Soak & Warm Up
When is the best time to visit Grey Highlands?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ562 | ﺩ.ﺇ555 | ﺩ.ﺇ562 | ﺩ.ﺇ529 | ﺩ.ﺇ661 | ﺩ.ﺇ602 | ﺩ.ﺇ606 | ﺩ.ﺇ643 | ﺩ.ﺇ573 | ﺩ.ﺇ599 | ﺩ.ﺇ621 | ﺩ.ﺇ738 |
| 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 ﺩ.ﺇ220 per night before taxes and fees

Verified guest reviews
Over 2,510 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

4.8 Average rating
Grey Highlands stays are highly rated by guests—averaging 4.8 out of 5!
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- Rentals with a kayak Grey County
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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
- Inglis Falls
- Caledon Ski Club LTD
- Harrison Park
- Forks of the Credit Provincial Park
- Wye Marsh Wildlife Centre
- Awenda Provincial Park
- Mono Cliffs Provincial Park
- Elora Quarry Conservation Area
- Sauble Beach
- Sunset Point Park
- Innisfil Beach Park
- Centennial Beach
- Island Lake Conservation Area
- Rockwood Conservation Area
- Sauble Falls Provincial Park




