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Cottage holiday rentals in Grey Highlands

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Top-rated cottage rentals in Grey Highlands

Guests agree: These cottages are highly rated for location, cleanliness and more.

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Cottage in Victoria Harbour

4.79 out of 5 average rating, 174 reviews

Serenity, Simplicity and Stone

This is a tiny cottage in a sleepy little hollow that opens onto the Georgian Bay. Inside, each stone was carefully chosen and the woodwork was built, piece by piece, by two craftsmen who are highly skilled and passionate about repurposing. It's an art that will leave you in awe; especially if you're worried about climate crisis. The coat hangers are upcycled 100-year-old railway spikes! If you're looking for luxury you might be disappointed but if you're a minimalist you're going to love it.

Guest favourite

Cottage in Meaford

4.93 out of 5 average rating, 165 reviews

Cosy and modern cottage on beautiful Georgian Bay

Enjoy panoramic views of Georgian Bay from this charming modern cottage on Paynter's Bay. Only eight minutes from Owen Sound, our cottage also borders on the quiet and beautiful Hibou Conservation Area where you can enjoy birding, hikes in forest and shoreline, and a great sandy beach and modern playground for the kids. Cuddle up next to the gorgeous modern Morso woodstove. Adventure awaits you with lots of skiing, biking, snowmobiling and the waterfall wonders of the Niagara Escarpment nearby.

Guest favourite

Cottage in Wasaga Beach

4.94 out of 5 average rating, 225 reviews

Charming riverside cottage, walk to beach

Charming riverside cottage available on Wasaga Beach. Just a 4-minute stroll from a pristine sand beach. Immerse yourself in nature's beauty while enjoying modern amenities, including a private hot tub for relaxation. Unwind with a friendly round of mini-golf or gather around the fire pit for cozy evenings under the stars.Create lasting memories at this perfect oasis that combines riverside tranquility, mini-golf fun, hot tub relaxation, and the warmth of a fire pit. Your dream getaway awaits!

Cottage in Tiny

4.87 out of 5 average rating, 109 reviews

The Lakeview cottage w/ hot tub

Welcome to our 4 season, 2 family cottage with Georgian Bay views and a hot tub. 3 min walk to the cutest small beach that has stunning sunsets, 12 min to Awenda Provincial Park which has great hiking, beaches, biking and winter activities. Short drive to Balm Beach. Downtown Midland has great restaurants and everything a quaint downtown has to offer. Winter has so much to offer including ice fishing, OFSC snowmobile trails, cross country skiing and much more. Max occupancy is 8 adult.

Cottage in Tobermory

4.88 out of 5 average rating, 110 reviews

7BR near Tobermory w/Golf Sim, Game Room & Hot Tub

Escape to a world of peace and tranquility at our private and secluded farmhouse-style cottage located in Wiarton. Surrounded by lush trees, this cottage offers the perfect retreat for families or friends. It's the ideal place for making memories. Great entertainment space, hot tub, NEW GOLF SIMULATOR and a cozy fireplace to gather around. On warm nights, relax on the large patio deck and gaze at the stars. This is a place you won't forget and will want to return to again and again.

Cottage in Gravenhurst

4.86 out of 5 average rating, 139 reviews

Muskoka Dream Cottage

Spectacular 4,200 square foot open concept custom luxury four season lakefront cottage in beautiful Gravenhurst Ontario. Great room boasts 26' high cathedral ceilings with gourmet kitchen and wood burning fireplace. The cottage boasts 3 bedrooms, 2 bathrooms upstairs. 1 bedroom and 1 bathroom on the main floor. Attached 2 bedroom bunkie is fully heated. Rental includes use of all non motorized water toys during the summer months including kayaks, paddle boards, canoe, and row boat.

Guest favourite

Cottage in Flesherton

4.94 out of 5 average rating, 137 reviews

All-Season Cottage on the Lake

An entire cottage all to yourself right on the water of Lake Eugenia in the Grey Highlands. This fully furnished 3-bedroom cottage is equipped with a brand-new kitchen, appliances, wood burning stove, furnace and water heater. You'll also have FREE access to unlimited WiFi, so you can work or stay in touch, when needed. Our cottage is suitable for a great get-away with any group, family or friends who are looking for a peaceful and enjoyable holiday from their busy lives.

Guest favourite

Cottage in Torrance

4.97 out of 5 average rating, 220 reviews

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Modern 4 season waterfront cottage! Stunning views! Located on picturesque Nine Mile Lake. Over 70% of the lake is crown land. Perfect for kayaking and canoeing to enjoy all the beauty Muskoka is known for. We have kayaks a canoe and a paddle board for you to enjoy. Plenty of sun exposure on the dock you can swim all day long. Close to hiking and snowmobile trails. May 15-Oct 2 Minimum 6 nights with a Sunday check in.

Guest favourite

Cottage in Grey Highlands

4.92 out of 5 average rating, 157 reviews

Hilltop garden cottage

enjoy a relaxing stay at a rustic family cottage with open concept for entertaining.relax in front of the fireplace with a glass of wine.Enjoy a morning coffee on the upper deck with a views of the gardens and lower deck for your family dinner in a peaceful setting . 2 minute walk to the lake at beach and boat launch or enjoy the many hiking trails including the Bruce trail with stunning views of Beaver Valley with local water falls.

Guest favourite

Cottage in Lion's Head

4.82 out of 5 average rating, 166 reviews

The Almost Waterfront - Lions Head Cottage

Lake view cottage only steps to the Sandy Lions Head Beach with Central air conditioning! The cottage is extremely clean, comfortable and well equipped with 3 bedrooms on the upper floor and 2 bedrooms on the ground floor with 3 full-size washrooms, a full kitchen and a large living area. Propane BBQ and fire pit on site. Within 5 min walk to restaurants, Pub, Grocery & Food store. 8 Adults Maximum NBP-2022-274

Cottage in Tiny

4.86 out of 5 average rating, 219 reviews

Georgian Bay Cottage - 100 Acres & Private Beach

THIS IS NOT a waterfront cottage, but it includes a separate PRIVATE gated beach LAKEFRONT property for your EXCLUSIVE USE! Our private two-acre gated beach at Marks Point, the western tip of Thunder Beach, is ten minutes by car from the cottage. The second beach option (public) is the unsurpassed 3km sand Thunder Beach, 5 minutes by foot! The cottage is on our private 100 acres.

Cottage in Lafontaine

4.82 out of 5 average rating, 230 reviews

Beach house (with pool open May-Oct)

Georgian Bay Beach club. Cute cottage perfect for families, couples, or anyone wanting to relax! 2 bedrooms, 1 bathroom, furnished, pool and private beach on the shores of beautiful Georgian Bay! Cottage is part of a 12 cottage community that shares the pool and beach area. Always super clean, professionally cleaned after every guest! Note: pool is closed October to mid May.

Holiday rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Houses

A space that's all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Grey Highlands cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Kimberley

4.85 out of 5 average rating, 332 reviews

A Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi

Guest favourite

Cottage in Tiny

4.96 out of 5 average rating, 225 reviews

Private 40 Acre Cottage with Hot Tub

Guest favourite

Cottage in Severn Bridge

5 out of 5 average rating, 115 reviews

CozyPeaceful LakeCottage HotTub CheckOutOurReviews

Cottage in Waubaushene

4.86 out of 5 average rating, 447 reviews

Charlie the Cottage | Hot Tub | Trail | Hike/Run

Guest favourite

Cottage in Gravenhurst

4.97 out of 5 average rating, 200 reviews

Muskoka Oasis: Hot Tub, Sauna & Nature Retreat

Guest favourite

Cottage in Port Severn

4.94 out of 5 average rating, 136 reviews

Muskoka Cottage on warm lake - 3 BR/2 BR/Hottub

Guest favourite

Cottage in Innisfil

4.89 out of 5 average rating, 161 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

Cottage in Orillia

4.87 out of 5 average rating, 103 reviews

FRIEND LAKE HOUSE

Pet-friendly cottage rentals

Guest favourite

Cottage in Meaford

4.95 out of 5 average rating, 93 reviews

Woodski Winter Haven: Mountain Cottage Near Skiing

Cottage in Flesherton

4.95 out of 5 average rating, 38 reviews

Four Season Waterfront Cottage on Lake Eugenia

Cottage in Tiny

4.94 out of 5 average rating, 142 reviews

Cozy 4 Season Family Cottage

Guest favourite

Cottage in Gravenhurst

4.88 out of 5 average rating, 118 reviews

Waterfront 3 BR Cottage 4 Seasons Gravenhurst Heat

Guest favourite

Cottage in Meaford

4.94 out of 5 average rating, 51 reviews

Charming 3bdrm cottage on Georgian Bay!

Cottage in Sauble Beach

4.72 out of 5 average rating, 72 reviews

My Blue Haven - Sauble Beach, Ontario

Guest favourite

Cottage in Tiny

4.87 out of 5 average rating, 39 reviews

Balm Beach Cottage: Hot Tub/GameRoom/more!

Guest favourite

Cottage in Sauble Beach

4.93 out of 5 average rating, 28 reviews

Sauble Beach - Quiet 4 Season Cottage Near Beach

Private cottage rentals

Guest favourite

Cottage in Wasaga Beach

4.86 out of 5 average rating, 22 reviews

The River's Edge - Cottage 1: The Riverbank House

Guest favourite

Cottage in Howdenvale

4.89 out of 5 average rating, 44 reviews

Beautiful Private Cottage on 10 Acres and a view!

Guest favourite

Cottage in Southgate

4.89 out of 5 average rating, 104 reviews

Thistle And Pine Cottage

Guest favourite

Cottage in Coldwater

4.97 out of 5 average rating, 38 reviews

Charming 3BR Cottage on Tranquil Lake 🐦🛶🎣🏊‍♀️

Guest favourite

Cottage in Tiny

4.97 out of 5 average rating, 36 reviews

2 Bedroom Plus Bunkie Woodland Beach Cottage

Cottage in Sauble Beach

4.88 out of 5 average rating, 26 reviews

Sauble Beach Front Cottage 2

Guest favourite

Cottage in Palgrave

4.99 out of 5 average rating, 207 reviews

Hockley valley, up country guest cottage

Cottage in Kemble

4.82 out of 5 average rating, 139 reviews

Georgian Bay Waterfront Oasis

Quick stats about cottage rentals in Grey Highlands

Total rentals
80 properties
Nightly prices starting at
$89 NZD before taxes and fees
Total number of reviews
3.2K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace

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