Cottage holiday rentals in Grey Highlands

4.87 out of 5 average rating, 166 reviews

A lakeside cottage is surrounded by tall trees, with a gentle slope leading to the water. A private dock is visible, along with several outdoor chairs. The cottage's warm glow is highlighted in the evening light, offering a welcoming appearance.

Cottage in Gravenhurst

Waterfront 3 BR Cottage 4 Seasons Gravenhurst Heat

4 Seasons: Heated+A|C! You and friends/family will enjoy easy access to everything Gravenhurst has to offer from our centrally located retreat cottage. Conveniently located on Pine Lake, you will have sun-filled water views throughout the cottage. We are located directly off the main highway, easy road access and parking. The lake is perfect for swimming and water sports. Get ready to sip your morning coffee on the back porch and watch the sun rise! A perfect spot for yoga and/or meditation.

4.97 out of 5 average rating, 127 reviews

The exterior of a modern cottage is framed by tall trees and colorful foliage. A spacious deck wraps around the cottage, providing outdoor seating options. The gravel pathway leads to the entrance, surrounded by natural landscaping and decorative stones.

Cottage in Tiny

Fall Escape - dazzling colours & stunning beach

Insta: @woodwardbythebeach 3min walk to the area’s most beautiful beach, sunsets & trails, you'll be sure to get lost in the serenity of the sand dunes year round Outdoor fire pit- s'mores included! Enjoy the BBQ, deck, & patio; the wine is on us! Fast WIFI for streaming movies or work from cottage Area is secluded yet central. 10min to Midland, close to Balm Beach - arcade, gokart, restaurant, & bar Ski/Hike/Snowmobile then unwind in a peaceful winterized home getaway with indoor fireplace

4.91 out of 5 average rating, 198 reviews

A charming modern cottage is set against a backdrop of lush greenery and clear blue skies. The exterior features large glass windows and a sloped roof. A patio area with natural stone and comfortable outdoor seating is highlighted, providing a welcoming space to enjoy the views.

Cottage in Meaford

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.

4.94 out of 5 average rating, 259 reviews

A circular stone fire pit is surrounded by wooden Adirondack chairs, offering a cozy gathering space. A vibrant fire burns in the center, with lush greenery and a serene riverside view in the background under a colorful sky.

Cottage in Wasaga Beach

Charming riverside cottage, B&B license

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!

4.91 out of 5 average rating, 343 reviews

Cottage in Kimberley

Vintage School House ~Hiking, Skiing, Pet Friendly

Gather with family or friends in this vintage 5 bedroom School House in the Beaver Valley. -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.

4.99 out of 5 average rating, 138 reviews

A modern cottage features a stone exterior with a sloped roof, harmoniously blending into the surrounding forest. A cozy propane fireplace is visible on the patio, which overlooks a gently flowing stream bordered by smooth stones and lush greenery.

Cottage in Southgate

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.

4.96 out of 5 average rating, 135 reviews

A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.

Cottage in Tiny

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.

4.94 out of 5 average rating, 131 reviews

An open concept living area showcases large panel doors that fully open to the outdoor deck. Inside, a comfortable seating arrangement is visible, along with a cozy area rug and a neutral color palette. Natural light floods the space, enhancing the connection to nature.

Cottage in Mono

Hockley Riverside Cottage • Loft and Bunkie

Needing an unforgettable escape? This cozy cottage is nestled in nature along the Nottawasaga river and has large panel doors that fully open for picture worthy views & peaceful sounds of the river. A new incredible outdoor fire-pit with hanging egg chairs. A cozy indoor wood burning fireplace along with a comfy pull out couch that has a projector above for the best movie nights. Heated floors if you aren't interested in maintaining a fire, fully equipped kitchen, Wi-fi, AC and washer/dryer.

Red Adirondack chairs are positioned on the dock, overlooking a sandy beach area and a lake. The cottage is visible in the background, surrounded by trees, with colorful kayaks resting on the shoreline. A welcoming atmosphere is created by the spacious outdoor setting.

4.91 out of 5 average rating, 111 reviews

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.

4.85 out of 5 average rating, 355 reviews

An indoor hot tub is surrounded by wooden paneling and large windows that allow sunlight to fill the space. Natural stone accents and a serene greenery image on the wall enhance the calming atmosphere. Two wooden chairs are positioned nearby for relaxation.

Cottage in Kimberley

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

30 minutes to Georgian Bay, 25 to Collingwood/Blue Mountain, and only 10 to Lake Eugenia's public beach. Our lovely, spacious, 5 Bed 5 bath retreat is nestled comfortably in the woods, convenient to almost every kind of activity and adventure. With 5 wash rooms and a large, INDOOR, jetted hot tub, it provides the perfect combination of convenience, relaxation, and outdoor adventure! BBQ, pool table, fireplace, fire pit, board games and high speed wifi. INSTA: @HIDDENHIDEOUTS

4.93 out of 5 average rating, 112 reviews

An open kitchen features modern stainless steel appliances, including an oven and refrigerator. A large window allows natural light to fill the space, with a dining table set for four. Greenery in a vase adds a touch of nature to the countertop.

Cottage in Meaford

New and Cozy Cottage Minutes to Georgian Bay!

Conveniently located near the amenities, shops, and restaurants of downtown Meaford, our cozy stay is just steps from the Georgian Trail, a short walk from Georgian Bay, and a quick 20-minute drive from Blue Mountain Ski Resort. In Meaford and the surrounding areas, you'll find tons of local options to ski, bike, hike, swim, fish, golf and relax with family and friends. Embrace the Grey Highland's year-round beauty and enjoy the perfect blend of relaxation and outdoor excitement!

4.98 out of 5 average rating, 147 reviews

A vibrant red cabin is surrounded by lush greenery, featuring a spacious elevated deck. A dining table with six chairs is set under a large umbrella, while a barbecue grill is positioned nearby. Large windows invite natural light into the interior.

Cottage in Elmwood

Little Red Cabin on the River

Bright and cozy, open concept cabin retreat overlooking Styx river in beautiful West Grey. Relax next to a quiet river on a large lot with elevated deck, natural wood-burning fire pit and BBQ. This all season get away is 2 hours from Toronto, perfect for small families or a small group. Recently updated, this cabin features simple, modern decor with a fully furnished kitchen for home cooked meals and baking. Also now includes WiFi and an outside wood burning, cedar barrel sauna.

Popular amenities for cottage rentals in Grey Highlands

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.96 out of 5 average rating, 130 reviews

The cottage exterior is presented with a welcoming front porch and charming double doors. Soft lighting highlights the staircase and surroundings, while landscaped greenery enhances the appeal. A combination of large windows and a gable roof contribute to the inviting architectural design.

Cottage in Southampton

Spa cottage: hot tub, sauna, cold plunge & firepit

4.9 out of 5 average rating, 240 reviews

A loft area features a wooden railing adorned with greenery, providing a cozy viewing spot. A circular wooden table is accompanied by two matching folding chairs, inviting relaxation. Warm lighting enhances the natural wood tones of the ceiling and walls, creating a welcoming ambiance.

Cottage in Alcona

Utopia villa and spa

4.94 out of 5 average rating, 120 reviews

The exterior of a cottage is shown, surrounded by lush greenery and blooming flowers. A stone pathway leads to the entrance, with a wooden deck overlooking the lake. The tranquil water and open sky are visible in the background, accented by a large tree providing shade.

Cottage in Orillia

Spacious Cottage Escape with Lakeside Hot Tub

4.94 out of 5 average rating, 103 reviews

A unique wooden sauna, shaped like a barrel, is placed on a grassy area by the lake. Above, a clear night sky is filled with bright stars, providing a serene backdrop. Nearby, lounge chairs are arranged on the lawn, with trees lining the water’s edge.

Cottage in Coldwater

Cottage on the Rocks - with Hot Tub and Sauna!

4.94 out of 5 average rating, 143 reviews

Cottage in Port Severn

Muskoka Cottage on warm lake - 4 BR/2 BR/Hottub

4.88 out of 5 average rating, 190 reviews

Large glass patio doors frame a scenic view of the waterfront, revealing a private deck with seating and a hot tub surrounded by trees. Sunlight casts a warm glow over the area, enhancing the sense of tranquility.

Cottage in Innisfil

Stunning Lakefront Cottage Hot Tub & Sauna

4.99 out of 5 average rating, 141 reviews

An aerial view of a cottage located on a waterfront lot is showcased, framed by lush greenery. A large deck and seating areas are visible, along with a hot tub and sauna. Several boats are docked at the waterfront, indicating access to water activities.

Cottage in Alcona

Charming waterfront cottage on Lake Simcoe

4.78 out of 5 average rating, 223 reviews

A waterfront deck is visible, featuring a hammock, lounge chairs, and umbrella-covered seating. Natural stone and a small stack of wood provide a rustic touch, while the calm water and distant trees create a serene setting.

Cottage in Owen Sound

Balmy Breezes - Waterfront Cottage with Hot Tub

Pet-friendly cottage rentals

A wooden deck extends over a calm pond, featuring two red Adirondack chairs and a matching bench. Lush greenery surrounds the water, with a windmill visible in the background under a clear blue sky.

5 out of 5 average rating, 66 reviews

Greenery Lane - w/ private pond, hot tub & sauna!

4.98 out of 5 average rating, 66 reviews

A spacious outdoor deck features lounge chairs arranged for relaxation, with an adjacent gazebo providing shade. A barbecue grill and outdoor bar area are visible, complemented by a pathway leading through the lush greenery towards a distant view of the water.

Cottage in Wasaga Beach

Charming cottage on the Beach

4.95 out of 5 average rating, 169 reviews

The cottage exterior features a large wrap-around deck furnished with outdoor tables and umbrellas. Lush greenery surrounds the area, contributing to a peaceful atmosphere. A stone pathway leads to the entrance, and firewood is neatly stacked underneath the deck.

Cottage in Tiny

Cozy 4 Season Family Cottage

4.92 out of 5 average rating, 165 reviews

The calm surface of Loon Lake is reflected, showcasing trees adorned with vibrant autumn foliage. The surrounding greenery is complemented by warm hues of red, orange, and yellow, creating a serene natural landscape. Sunlight glimmers on the still water.

Cottage in Gravenhurst

Waterfront @Muskoka Pines /kayaks/bbq/firepit

4.81 out of 5 average rating, 173 reviews

A serene lakeside scene is captured at sunset, with vibrant hues of pink and purple reflecting on calm waters. Silhouetted trees line the shore, and subtle rock formations add depth to the landscape.

Cottage in Waubaushene

The Cottage on Coldwater; where bay & trail meet.

4.72 out of 5 average rating, 384 reviews

The exterior of the studio apartment is shown, featuring a combination of white and gray siding. A modern garage door and a front door are visible, framed by a small patio area. Trees provide a natural backdrop, with Lake Simcoe glimpsed in the distance.

Cottage in Barrie

The Guesthouse on the North Shore Trail

4.92 out of 5 average rating, 108 reviews

A modern, lakefront cottage is nestled among tall pine trees, with a sloped wooden staircase leading up to its large, wraparound deck. Snow blankets the ground, and the cottage exterior is painted in shades of blue, reflecting its natural surroundings.

Cottage in Port Severn

Tree Tops on Six Mile Lake

4.94 out of 5 average rating, 111 reviews

Cottage in Mar

Whiskey Harbour Lakehouse - Lake Huron Getaway

Private cottage rentals

A charming cottage is nestled among trees, featuring a spacious elevated deck with a glass railing. Seating areas are arranged outside, complemented by a hot tub nearby. The Canadian flag flutters in the breeze, adding a welcoming touch to the serene setting.

4.95 out of 5 average rating, 40 reviews

Four Season Waterfront Cottage on Lake Eugenia

4.98 out of 5 average rating, 126 reviews

A wooden deck features several red Adirondack chairs facing the water, offering scenic views of Colpoy's Bay. Surrounding trees display vibrant autumn colors, complementing the calm blue water. Sunlight casts a warm glow on the deck, enhancing the serene atmosphere of the outdoor space.

Cottage in Wiarton

Waterfront Cottage by Bruce Trail

4.81 out of 5 average rating, 70 reviews

A cozy kitchen area features a wooden dining table set for four, complete with plates and glasses. Large glass doors provide natural light and views of the outdoors. Kitchen appliances, including a refrigerator and a stove, are visible, alongside wooden accents and shelving.

Cottage in Singhampton

Serenity Cottage Getaway - Perfect for Families

A comfortable living area features a large sectional sofa alongside a cozy armchair. Sunlight pours through multiple windows that provide views of the lake. A wood-burning stove and a coffee table sit centrally, with wooden walls enhancing the rustic ambiance.

5 out of 5 average rating, 21 reviews

Lake Eugenia Renovated Waterfront Cottage

4.87 out of 5 average rating, 71 reviews

A rustic log home is nestled among tall trees, approached by a dirt driveway lined with grass. The warm exterior of the home is complemented by a blue sky and scattered clouds, indicating a serene setting in the woods.

Cottage in Berkeley

Fortress of Solitude

4.85 out of 5 average rating, 168 reviews

The image captures a serene sunset over the water, with vibrant colors reflecting off the lake surface. Two trees silhouette against the backdrop, and gentle waves can be seen lapping at the shore, creating a tranquil atmosphere.

Cottage in Kemble

Georgian Bay Waterfront Oasis

4.96 out of 5 average rating, 73 reviews

A charming two-story home features natural wood siding with a welcoming front porch. Two wicker chairs are set on the porch, complemented by decorative planters. Lush greenery surrounds the property, enhancing the inviting atmosphere.

Cottage in Meaford

The Avalon - Entire home steps to Meaford Harbour

A cozy living area features a light-colored leather sofa set with two cushions and a rustic wooden side table. Warm wooden paneling adds to the inviting atmosphere, while soft lighting enhances the comfort. A flat-screen TV is mounted on the wall, and adjacent rooms are visible.