House holiday rentals in Grey Highlands

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Top-rated house rentals in Grey Highlands

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Guest favourite

Home in Collingwood

4.85 out of 5 average rating, 110 reviews

Bright & Cozy Getaway by the Lake In Collingwood

Walking distance to Georgian Bay & minutes drive to Blue Mountain Resort/Collingwood city center Skiing, golfing, cycling trails, exploring historical downtown, & an incredible array of culinary options! ✔Master Ensuite w/Large Spa Tub ✔65-inch TV w/ Netflix, Crave, Cable ✔Hi-Speed WiFi: Multiple Device Steaming & Video Conferencing ✔Fully-Stocked Kitchen w/ Stainless Steel Appliances ✔2-Car Garage + 2 Car Driveway Parking ✔2 Queen-Sized Beds ✔Washer/Dryer ✔AC ✔All Units Main Floor Accessible

Guest favourite

Home in Meaford

4.87 out of 5 average rating, 278 reviews

Beachhouse Hideaway - Hot Tub, G-Bay Waterfront

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

Guest favourite

Home in Meaford

4.96 out of 5 average rating, 111 reviews

Close to Hiking & Beach with Large Fenced in Yard

Whether you are looking to rest and recharge or head out on an epic adventure in the hills, this comfortable century home is the perfect base. Nestled in the quaint town of Meaford the home is walking distance to everything you need for a great stay. It has a large backyard, fire area, patios, laundry, stocked kitchen & two living rooms. The recently updated home is set up perfectly for families & smaller sized groups. The large fenced in backyard is perfect for pets and a great space for kids.

Guest favourite

Home in Meaford

4.96 out of 5 average rating, 146 reviews

Redhill Luxury Home...by the Blue Mountains

This eco friendly house of 4,500 sq ft is bright, modern, luxurious on 50 acres of rolling hills with a beautiful pond and hiking trails. All bedroom ensuite plus two extra full bathrooms. Comfortably sleeps up to 24 guests. Amazing view, sunset and star gazing. Salt water pool in the summer. Outdoor BBQ, fire pit, Hot Tub year round. Minutes to Christie beach, ski hills, golf courses, Bruce Trail. Enjoy snowshoeing, cross country. Serenity on top of the hill! See more info under the space.

Guest favourite

Home in Penetanguishene

4.97 out of 5 average rating, 144 reviews

White Rolling Sands of Penetang by Theatre

Enjoy a firepit in the private backyard of a large deep lot backing onto woods with trails. Local walking and cycling routes, or stay home and enjoy the veggie and flower gardens from back deck. Fully licensed and located close to Kings' Wharf Theatre / Discovery Harbour. Experience the natural beauty of Tiny Beaches, Georgian Bay Islands N.P and Awenda P.P. nearby (Park pass available for use). Marinas, beaches, boat cruise of the islands, Ste Marie Among the Hurons and Wye Marsh are nearby.

Guest favourite

Home in Meaford

4.96 out of 5 average rating, 134 reviews

The Meaford Retreat! Beautiful Home on Wooded Lot.

This beautiful Century home sits on a mature wooded lot less than a 1 min walk to a large conservation area with trails scenic in both summer and winter! Connect with nature whilst still being a 5 min walk from main street and harbour boasting shops, restaurants and cafes. Touching distance of Blue Mountains, Owen Sound, Thornbury and Collingwood. Hot Tub & Sauna available October-May inclusive Fast WiFi 4 vehicle parking Front and back decks to enjoy your morning coffee. Beautiful!!

Guest favourite

Home in Duntroon

4.89 out of 5 average rating, 172 reviews

Country Retreat with views of Georgian Bay

Located minutes from Collingwood, The Blue Mountains, Creemore and Wasaga Beach. This is a four season resort, with ski hills, fishing, trail riding, rock climbing, golfing and more. Our home has views of Georgian Bay with an upper balcony to sit out and enjoy your morning coffee or tea. Spacious Kitchen, Dining Room, Great Room, Recreation Room, and bedrooms. Office space with desk and wifi for your convenience. You can visit South Georgian Bay Tourism's website for things to do.

Superhost

Home in The Blue Mountains

4.91 out of 5 average rating, 169 reviews

Pool Open/Sauna/Shuttle Bus/Entertainment/2 King b

Large home in the Snowbridge resort with 2 King Beds. Outdoor heated pool opens May 18. Sauna and Entertainment basement is ready for guests. Walk to the Village. Walk to Pool in 1 minute from our home This four-bedroom pad is the perfect spacious getaway to relax with your family/friends. Enjoy views of alpine range from your master bedroom and second bedroom. No need to fight for showers as we have 5 Bathrooms. It's very rare to find a community with a Heated Outdoor Pool

Guest favourite

Home in The Blue Mountains

4.95 out of 5 average rating, 149 reviews

Serene mountainside home View/Shuttle Bus/Pool

Welcome to this peaceful haven within the mountains. We have decorated our spacious and cozy home with comfortable beds, ample living amenities, and high-quality furniture to welcome you, your family and friends. Enjoy the carefully curated art pieces collected from around the world and look upon a stunning view of the snow-capped mountains from the master bedroom. Heated outdoor pool is seasonal! Walkable to the Village. Free Shuttle Bus. Pool is open from May 18

Guest favourite

Home in The Blue Mountains

4.96 out of 5 average rating, 299 reviews

The Blue Mountain Cedar Chalet /walk to village

Luxury Directly Across from the Village! Unit 216 Mountain Walk Fully Renovated and Fully Stocked Modern kitchen with everything you need Coffee, teas, spices, oil, vinegar included Lots of linens, towels, extra blankets Balcony with BBQ Pack n' play, highchair Lego, playmobil, boardgames, XboxOne 2 TV with Netflix, Prime, Crave, Disney+, Cable Fast WiFi Free Parking for Three Cars NO. LCSTR20220000081

Guest favourite

Home in Kimberley

4.88 out of 5 average rating, 176 reviews

Heart of Kimberley - with views and a hot tub

Welcome to the hamlet of Kimberley nestled in the Beaver Valley. Surrounded by nature, the Rock House is a historic six bedroom century home with beautiful views close to many outdoor activities, and located beside an unassuming gourmet restaurant and a general store with fresh coffee and in-house sourdough bread. We are located 25 minutes from Blue Mountain and 2 minutes from Beaver Valley Ski Club.

Guest favourite

Home in Grey Highlands

4.96 out of 5 average rating, 126 reviews

Newly Renovated! Charming Beaver Valley Farmhouse

Quintessential Ontario 4+ bedroom century old farmhouse sitting on three private acres, comfortably updated and perfect for a quiet country getaway. Minutes from Lake Eugenia, Bruce Trail hiking and Beaver Valley Ski Club. 30 minutes to Thornbury, Collingwood, and the Blue Mountain. Enjoy the Grey Highland outdoors and relax by the wood burning fire.