
Waterfront holiday rentals in Grey Highlands
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Top-rated waterfront rentals in Grey Highlands
Guests agree: these waterfront rentals 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

Decked in Old Hollywood Glam @ The Beachhouse POM
This beach house was designed with relaxation and the enjoyment of togetherness in mind. Let your worries melt away as you slip into the warmth of this water side hot tub featuring stunning view across Georgian Bay and up the mountain side, as fresh snow falls around you. The open concept design makes this the perfect place to gather with family and friends w/ walkout waterfront patio and dock access for swimming. 2 min to downtown Meaford, 20 min to Blue Mtn, 1.5 hrs to Tobermory. Hiking Trails

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.

Luxurious Creek Retreat With Hot Tub
Welcome to this luxury cottage on the water. The perfect place to relax and unwind while listening to the waterfall and babbling brook flowing past only a few feet away. If you're looking for privacy and tranquility along with all the pleasures of a luxury stay then look no further. This property boasts a propane fireplace inside as well as one outside, in-floor heat and A/C. Fully equipped kitchen, two bedrooms with hotel quality mattresses and a bathroom that exudes high-end style and decor.

Beautiful Riverside Country Apartment
Bright, warm and newly renovated, this 900sqft apartment, a private floor of a charming country home with separate entrance and garden patio, awaits you in Melancthon. SmartHDTV, Wifi, tranquil surroundings, and next to the Bruce Trail. Close to Shelburne, Mansfield, Creemore, and many excellent restaurants (like The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, and Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

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.

The Carriage House @ Trillium Shores, Lake Eugenia
Discover this 30 ACRE year round Lake Eugenia retreat offering woodland, parkland, 3 lakefront access points with 2 docks, 2 spring fed ponds, 2000ft of shoreline! ONLY YOU AND YOUR FRIENDS/FAMILY HAVE USE OF THE ENTIRE BUILDING!!! Only 2 hrs north of Toronto! This is an UPPER STOREY LOFT accommodation. Guests MUST BE ABLE TO CLIMB STAIRS! Large upper storey deck with loungers, table, chairs, and BBQ for alfresco dining when the weather permits. Grey Highlands Licence #STA-2021-30-H

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.

Cozy, quiet, clean cabin with wi-fi and fire pit.
Welcome to Penny Creek. A simple cabin just south of Durham. A private location surrounded by ponds, streams and forest - yet close to many day adventures should you want to explore beyond the property. Nearby amenities include restaurants, grocery, lcbo, fuel, coffee and shopping . An open concept space that offers one queen bed and a pull out sofa. Full kitchen and bath. Picnic tables, Fire pit and bbq. Excellent hiking trails nearby. Easy access to ofsc (snowmobile) trails!

Thistle And Pine Cottage
Relax and unwind with the whole family at this peaceful place in the country. The cottage is on 50 acres that you have full access to. Great for swimming, walking, biking, cross country skiing, and much more. This 1 bedroom plus pullout couch(with privacy) is complete with kitchen, bathroom, and livingroom, and swimming pond with beach and Fire pit area that overlooks the pond. Perfect for a family of 4 or a romantic getaway for 2. Find us on Instagram @thistleandpine.cottage

GATED RESORT COTTAGE
[CLICK SHOW MORE FOR IMPORTANT INFO] Sought-after cottage located in the gated Wasaga Country Life resort; professionally managed year-round by Parkbridge. A short walk from the beach with full access to resort amenities including; indoor/outdoor swimming pools, private trails, playgrounds, mini golf, sports fields and many more professionally managed facilities. View the "Where you'll be" section below for a full list of amenities.
Popular amenities for waterfront rentals in Grey Highlands
Waterfront apartment rentals

Stunning 1 Bedroom unit

Luxury Serene Escape @ Friday Harbour Resort

Modern Luxury Delight with a Pool and Hot Tub

Trendy 1 Bdrm w/Pool & Hot Tub View

Beautiful Modern 2 Bedroom Apt.

2 Bedroom Luxury Suite @ Friday Harbour Resort

NEW Luxurious Corner Unit at Friday Harbour Resort

Cabin A in Wymbolwood Lodge
Waterfront house rentals

Underhill Riverside Retreat-Nature Preserve

Hillside Haven Retreat: Sunroom & Pond Escape

Stonefox Retreat: Acerage, Pond, Hot Tub & Sauna

Happy Valley Ski Golf Spa Relax

Brewster's Lake Escape | Lakefront in Singhampton

Cozy Cabin Vibes - Hot Tub• Firepit• Snowy Retreat

House on the bank of river

King Bed Farmhouse- w/ Fire-pit, 75" TV, Ping Pong
Waterfront apartment rentals

Cozy Stays – Your Fall Getaway at Friday Harbour

2BR Getaway at Friday Harbour All Season Resort

Stylish getaway condo, resort living

Designer Condo with beautiful harbour view.

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

Friday Harbour Luxury Condo Escape, Sleeps 4

Resort Condo in Friday Harbour

Marina view at Friday Harbour 2bd/2bth Pool option
When is the best time to visit Grey Highlands?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $192 SGD | $197 SGD | $188 SGD | $194 SGD | $224 SGD | $247 SGD | $259 SGD | $279 SGD | $242 SGD | $196 SGD | $194 SGD | $234 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 waterfront rentals in Grey Highlands

Total holiday rentals
Explore 100 holiday rentals in Grey Highlands

Nightly prices starting at
Grey Highlands holiday rentals start at $64 SGD per night before taxes and fees

Verified guest reviews
Over 3,070 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
90 of Grey Highlands holiday rentals include wifi 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
- Cobble Beach Golf Resort Community
- Beaver Valley Ski Club
- Mount St. Louis Moonstone
- Devil's Glen Country Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- TPC Toronto at Osprey Valley
- The Georgian Peaks Club
- Caledon Country Club
- The Club At Bond Head
- Sauble Beach Park
- The Georgian Bay Club
- Barrie Country Club
- Alpine Ski Club
- Mansfield Ski Club
- Toronto Ski Club
- Inglis Falls
- Horseshoe Adventure Park
- Legacy Ridge Golf Club
- Springwater Golf Course
- Heritage Hills Golf Club
- National Pines Golf Club




