Family-friendly holiday rentals in Tobermory

The exterior of a two-story cottage features a spacious lower deck with seating and stairs leading to the upper level. Large windows allow natural light to fill the interior. Lush greenery surrounds the property, creating a natural landscape.

4.95 out of 5 average rating, 255 reviews

Lakeside Lounge

Relax with the whole family at this peaceful Lakeside getaway. Enjoy incredible sunset views from the 64 ft elevated deck! The shallow water out front is sure to keep the kids entertained. Plenty of water toys to play with ensures fun for everyone on those hot sunny days and at night you’ll love the built-in fire pit right on the dock! The gourmet kitchen, fireplace and spacious interior are just some of the highlights here. Located just 5 minutes away from the Grotto and Singing Sands Beach!

4.95 out of 5 average rating, 181 reviews

A charming barn conversion is pictured, with a unique stone exterior and a distinct blue and gray metal roof. A welcoming entrance is highlighted by a red door and a covered porch. The surrounding yard is adorned with greenery and autumn leaves.

Barn in Lion's Head

The Stone Barn @ Lion's Head

Explore winter on The Bruce Peninsula! Discover our charming 1920s barn conversion, nestled in the heart of the Bruce Peninsula. This cozy retreat accommodates up to 5 guests in 3 spacious bedrooms. Unwind in the inviting living room, prepare meals in the fully-equipped kitchen, and gather around the outdoor fire pit. Explore nearby attractions, including Georgian Bay, Bruce Trail, Lion's Head, Tobermory, and Bruce Peninsula National Park. Book now for a memorable stay! Permit #STA-2024-248

A serene view of Georgian Bay is captured at sunset, with vibrant hues reflected in the water. The foreground features trees, framing the water's edge, while a boat is docked in the harbor, indicating a peaceful coastal setting.

4.99 out of 5 average rating, 201 reviews

Westwater Guest Suite (Waterview Private Unit)

Sit on your private water view deck enjoying the beautiful view of the Georgian Bay. Wake up to the beautiful morning sunrise while sipping on a cup of coffee, or enjoy the stunning sunsets while sipping on a glass of wine. During the day you are just steps away from the picturesque downtown, shopping, restaurants, bars, tours, and world class scenery are just steps away. Or take a short drive to Bruce Peninsula National Park (Grotto), Singing Sands or take a tour boat to Flowerpot Island.

A bright living area features a spacious sectional sofa adorned with textured cushions and a soft throw. Sunlight filters through large windows, revealing views of the surrounding forest. A comfortable armchair sits nearby, complemented by a small side table and a stylish light fixture.

4.88 out of 5 average rating, 106 reviews

Evenstar - Luxury in Nature

Winters at Evenstar are for snuggling under blankets, hot outdoor showers, and campfires in the snow. Quiet, peaceful, romantic, no neighbours in sight. 💕 Immerse yourself in two acres of untouched natural beauty, showcasing the unique ecosystems of the Northern Bruce Peninsula. With forest, alvar, and watercourse, this retreat is a haven for nature enthusiasts. 5 min walk to Lake Huron & Johnson's Harbour waterfronts. Central drive to Singing Sands, Grotto, Tobermory & Lions Head.

An open deck features comfortable seating arrangements with white frames and blue cushions, overlooking the tranquil waters. A round wooden dining table sits adjacent to the lounge area, with views of the natural landscape and distant islands enhancing the outdoor space.

5 out of 5 average rating, 234 reviews

Luxury Waterfront Cottage in Tobermory

Welcome to Tobermory Shores, the perfect waterfront destination for families and mature older adults seeking peace and relaxation while exploring the majestic Northern Bruce Peninsula. Located at the tip of the Bruce Peninsula along the Niagara Escarpment, Tobermory Shores offers breathtaking views of the crystal clear waters of Georgian Bay and Flowerpot Island and is only a 3-minute drive to downtown Tobermory, 15 minutes to Bruce Peninsula National Park and the world-famous Grotto.

4.92 out of 5 average rating, 277 reviews

A winter scene captures a cozy retreat surrounded by snow-covered trees. The cabin features a welcoming deck, with sunlight peeking through the clouds as a colorful sunset casts a warm glow over the landscape. A nearby sauna adds charm to the serene environment.

Cabin in Lion's Head

Little Lake Lookout: Sauna, Beach, Dock, Dogs!

Escape to Little Lake Lookout! This serene 2-bedroom + loft and 2-bath retreat boasts 170ft of private lakefront on Little Lake. Enjoy stunning views of the Niagara Escarpment and an abundance of nature and wildlife. With all-season amenities and a scenic drive from the GTA and London, this dog-friendly oasis (we're fenced!) is the perfect getaway for making memories. Only 7 minutes from the charming village of Lion's Head. Book now for a truly unique experience! @NorthPawProperties

A cottage elevated on a wooden deck is surrounded by tall trees under a starry night sky. Warm light spills from the windows, creating a cozy ambiance. A staircase leads up to the entrance, while a pathway and gathering area with seating are visible in the foreground.

5 out of 5 average rating, 113 reviews

Blue Feather Lake House - Tobermory

Welcome to Blue Feather Lake House. On our first day here we found a blue jay feather under the trees and “Blue Feather” was born. We are located on Larry’s Lake in Dorcas Bay on the Lake Huron side of the peninsula. This means beautiful sunsets, a family friendly lake, peace and tranquility. We are a short drive from Johnson’s Harbour, Singing Sands beach and Bruce Peninsula National Park and 20 min to downtown Tobermory. We hope you enjoy our space and the area as much as we do!

4.89 out of 5 average rating, 272 reviews

A wooden dock extends over calm waters, silhouetted against a sunset sky. Several Muskoka chairs are arranged along the edge of the dock, inviting guests to enjoy views of the tranquil lake and distant shoreline.

Cabin in Tobermory

Sauna Lake Huron Tobermory

Hudson's Rock located on the shores of Lake Huron just 10 min from downtown Tobermory. This cozy 3BR cabin is the perfect spot to make memories, whether cuddling up beside the cozy fire or playing board games with the family. Inside the warmth of the wood will instantly relax you while giving you all the amenities of home. Steps away from the waters edge, days can be spent swimming, kayaking, Sauna or soaking up the sun You'll have everything your family could want or need !

4.87 out of 5 average rating, 129 reviews

A fire pit is situated amidst smooth stones, casting a warm glow. Two red adirondack chairs are positioned nearby, inviting relaxation. The words "Life is Better By The Fire" are etched into the fire pit, surrounded by a dark, natural setting.

Cabin in Tobermory

Tobermory Stargazing Retreat

Keep life simple at this peaceful and centrally located cottage. Just 10 minutes from Tobermory, The Grotto, Singing Sands, and Little cove. Family friendly 3 Bedroom and 2 Full bathrooms with a private 25 acre forest to explore and water access to Lake Huron for swimming and sunsets just a quick 15min walk away. Quality time with family and friends is easy here! Winter - 5 Adult and 2 Youth Snowshoes available for guests! STA# NBP-2022-189 6 Adults Maximum + 2 Children

A spacious waterfront cottage is set against a backdrop of lush greenery and clear blue skies. The structure features multiple large windows, allowing for ample natural light. A rocky shoreline runs along the water's edge, providing a beautiful view of the surrounding nature.

4.98 out of 5 average rating, 320 reviews

Tamarack by the Bay - Waterfront Cottage

Location; location; location. Spectacular year round waterfront cottage on Lake Huron 10 minutes from Tobermory. Featured in an article of Trips to Discover. Entire main floor walkout, 9 foot ceilings and 2 decks await your visit. Private access to the water along with supplied kayaks and paddleboard enhance your stay. Large firepit will allow for many hours of evening entertainment. See video tours on You Tube: "Welcome to Tamarack By The Bay" by CL Visuals and Calvin Lu.

The cabin's exterior features a rustic design with log siding and a bright red door. A charming sign reading 'Goose Creek' is displayed above the entrance. Two red chairs and a small white side table are positioned on the wooden deck, surrounded by greenery.

4.85 out of 5 average rating, 120 reviews

Goose Creek Log Cabin

Welcome to Goose Creek Cabin! Come and enjoy a cabin experience at Goose Creek Cabin, a perfect mix of rustic and modern. Newly renovated, this cozy retreat is ideal for 4 guests. Nestled on a private, wooded lot, it offers tranquillity after exploring Tobermory. Conveniently, it's just a short walk to downtown Tobermory and the head of the Bruce Trail. Please bring all required bedding and towels for your stay. Managed by Vibe Getaways - @tobermoryvibes

4.99 out of 5 average rating, 143 reviews

A secluded cordwood cabin is nestled in a snowy forest landscape, surrounded by tall evergreen trees blanketed in white. The cabin features a stone exterior and a distinctive overhanging roof, with a wooden door and two small windows, creating a cozy, rustic presence against the winter scenery.

Cabin in Chatsworth

Peaceful cabin-in-the-woods 50 acre private forest

Relax in a charming cordwood cabin on an off-grid property powered entirely by solar energy. Enjoy exclusive use of 50 acres of varied woodlands with over 4km marked & maintained nature trails (loaner snowshoes provided!) and special features like a SoundForest, a meditative walking labyrinth, plus a sauna made of local cedar... it’s like having your own private park! There’s even an option ($) to have a breakfast basket brought out.

Popular amenities for Tobermory family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 142 reviews

Tiny home in Kimberley

Boho Beaver Cabin 1 with saltwater hot tub

Loft in Blue Mountain Resort Area

A cozy living area features a comfortable grey sectional sofa facing a modern television. A wooden coffee table rests in the center, accompanied by a soft decorative pillow. Natural light enters through large windows with dark curtains, offering views of the snowy outdoor landscape.

4.79 out of 5 average rating, 141 reviews

Sunshine Summit | Ski-In-Out, Shuttle & Hot Tub

4.94 out of 5 average rating, 234 reviews

A traditional Mongolian yurt features a white exterior adorned with blue patterns, supported by wooden poles. Two wooden adirondack chairs sit on a circular stone patio, inviting relaxation in the natural surroundings, with trees visible in the background.

Yurt in Priceville

Natural Mongolian Yurt on Biodynamic Farm and Spa

4.97 out of 5 average rating, 183 reviews

Home in Wiarton

Kiss & Bond Water View Colpoys Bay 4 -Seasons

The studio features a spacious living area with a comfortable sofa and a modern armchair. A king bed adorned with blue and yellow linens is positioned in the background. Natural light filters through the window treatments, enhancing the serene ambiance.

4.83 out of 5 average rating, 436 reviews

Ski in/out @ North Creek W King bed! New Hot Tub

Flat in Blue Mountain Resort Area

A cozy sleeping area is highlighted by a black wooden bed frame with a crisp white bedding set. Decorative pillows are arranged on the bed, while a framed image of a bear adorns the wall. Soft bedside lighting is provided by sconces, complementing the mirror opposite.

4.91 out of 5 average rating, 171 reviews

Blue Mountain Studio Retreat

Flat in Blue Mountain Resort Area

The airy studio unit features a spacious king bed framed by green accent walls. A cozy sectional sofa is positioned in front of a coffee table. Natural light filters through window shutters, highlighting the adjacent balcony with Muskoka chairs.

4.96 out of 5 average rating, 341 reviews

Studio at Blue-KingBed/Pool/HotTub/Shuttle

An open concept living area features a spacious gray sofa and a sleek coffee table. Large windows allow natural light and offer views of greenery outside. A mounted TV is positioned above a modern fireplace, with two high-backed chairs at a nearby counter for additional seating.

4.86 out of 5 average rating, 257 reviews

Sweet Retreat / Ski-In Ski-Out, Shuttle & Hot Tub

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 147 reviews

A cozy cottage corner features large windows that invite natural light. A teepee with glowing candles provides an enchanting outdoor setting. The living area showcases comfortable seating and decorative pillows. A charming bedroom offers a colorful bedspread and unique lighting, while a hammock hangs between trees for relaxation.

Cabin in Miller Lake

Cottage on 24 Acres: a Nature Lover’s paradise

4.95 out of 5 average rating, 185 reviews

A well-lit living area features two comfortable gray sofas adorned with patterned throw pillows. Warm wooden floors complement the neutral wall tones. A staircase with wooden steps leads to the upper level, while large windows allow natural light to brighten the space.

Home in Williamsford

Williamsford Blacksmith Shop

4.97 out of 5 average rating, 107 reviews

The Lodge is surrounded by lush greenery and features a wraparound deck with outdoor seating. A gentle stream flows nearby, accentuating the natural landscape. The rustic exterior blends seamlessly with the forested backdrop, providing a peaceful and private retreat.

Chalet in Markdale

Grey Highlands Lodge

4.85 out of 5 average rating, 129 reviews

A charming cottage is nestled among vibrant autumn trees, showcasing hues of orange, yellow, and green. The cottage features a modest porch and seating area, surrounded by an open lawn that gently slopes toward the foreground, creating a serene and inviting outdoor space.

Cottage in Miller Lake

Cozy 1 Bedroom Cottage with Lake View

4.96 out of 5 average rating, 159 reviews

A charming wood cabin is set in a grassy area, surrounded by tall trees. The front porch features a small table and chairs, with a vibrant pumpkin and seasonal flowers nearby. The cabin has a sloped roof and multiple windows that invite natural light.

Cabin in Port Elgin

Serene and Cozy Cabin

A wooden dock extends over calm waters, bordered by trees. Four classic Adirondack chairs are positioned invitingly along the edge, offering a serene spot to enjoy the waterfront view. The soft natural colors of the surroundings enhance the peaceful ambiance.

4.83 out of 5 average rating, 109 reviews

Stella by Starlight

4.93 out of 5 average rating, 122 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!

4.97 out of 5 average rating, 146 reviews

Cottage in Tiny

Ultimate Georgian Bay Vacation Getaway

Family-friendly home rentals with a pool

A spacious open-concept living area is highlighted, featuring a large dining table set for meals. The kitchen is equipped with modern appliances and black cabinetry. Natural light enters through multiple windows, enhancing the inviting atmosphere of the space.

4.98 out of 5 average rating, 191 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

The inviting living area features a large, comfortable couch and an armchair, with a coffee table centrally located. A fireplace adds warmth, and a wall-mounted TV is positioned above it. The open layout connects to a modern kitchen equipped with dining space for four.

4.9 out of 5 average rating, 146 reviews

Blue Mountain Getaway at North Creek Resort

4.93 out of 5 average rating, 120 reviews

Cottage in Meaford

Woodski Winter Haven | Cozy Ski Stay + Hot Tub

Townhouse in Blue Mountain Resort Area

A spacious living area features tall windows allowing natural light to fill the room. A large screen TV is mounted above a gas fireplace, surrounded by comfortable seating. Decorative pillows enhance the sectional sofa, and an elegant coffee table sits centrally, adding to the inviting atmosphere.

4.97 out of 5 average rating, 231 reviews

Après Blue- 2bed2bath w/Pool 6 min walk to village

A cozy family room features a spacious gray sectional sofa and a wooden coffee table. Light-colored walls and a patterned rug create a welcoming atmosphere. In the background, a kitchen area is visible, equipped with modern appliances and seating for two.

4.93 out of 5 average rating, 317 reviews

Cozy Studio Mountainside stay in Blue Mountains

Flat in Blue Mountain Resort Area

An open-concept studio unit is shown, featuring a cozy living area with a dark sectional sofa and a wooden coffee table. The king bed is visible in the background, accompanied by modern bedding. The kitchen area includes a bar with stools and is equipped with countertop appliances.

4.98 out of 5 average rating, 131 reviews

Alpine Bliss: King Bed/Pool/HotTub/Shuttle

Chalet in Blue Mountain Resort Area

A bright bedroom features a spacious bed covered with soft linens and a textured throw. The walls are painted blue, complemented by decorative curtains. A piece of artwork depicting a deer is displayed above the bed, and a bedside lamp is positioned on a small white table.

4.97 out of 5 average rating, 305 reviews

The Little Blue Spruce! Free shuttle to village

A cozy living area is presented with two sofas and a fabric armchair, arranged around a wooden coffee table. A gas fireplace sits beneath a wall-mounted television. Large windows allow natural light, offering views of the surrounding landscape.