
Holiday rentals with a kayak in Grey Highlands
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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

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.

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.

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.

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.

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

Welcoming Waterfront Cottage

New look The Greenview Retreat

Modern Country Getaway by the Bay

Peaks in The Happy Valley

The Cedar House

Georgian Bay Vibes, Relax and Reset in Meaford

Kiss & Bond Water View Colpoys Bay 4 -Seasons

Serene Waterfront Escape On Private Lane
Cottage rentals with a kayak

Serenity Cottage, Jetski, Hot Tub, Ice rink

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

Waterfront Paradise on the Georgian Bay

2 BEDRM WATERFRONT COTTAGE, CANOE, KAYAKS, WIFI

The Gingerbread House | Near Lake + Wedding Venues

Luxury Lakehouse Hot Tub Private Beach Lake Simcoe

✦9Bedroom✦8400sqft Farm House ✦28Acres ✦1HrToronto

Forest Harbour Hideaway
Cabin rentals with a kayak

Waterfront Cottage on Severn Falls

Muskoka Haven, the Colonel's cottage

Island Cottage Georgian Bay 3

The Blue Cottage

Deer Park, Cozy Cabin with Hot Tub, Amazing View

Hawthorn Cottages - Bunkie #1

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 | $193 SGD | $191 SGD | $193 SGD | $182 SGD | $227 SGD | $207 SGD | $208 SGD | $221 SGD | $197 SGD | $206 SGD | $213 SGD | $254 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 |
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 $76 SGD 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 & 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

4.8 Average rating
Grey Highlands stays are highly rated by guests – averaging 4.8 out of 5!
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- Rentals with a sauna Grey Highlands
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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
- Centennial Beach
- Innisfil Beach Park
- Sunset Point Park
- Island Lake Conservation Area
- Sauble Falls Provincial Park
- Rockwood Conservation Area




