Family-friendly holiday rentals in Lion&#x27;s Head

4.98 out of 5 average rating, 167 reviews

The exterior of a charming tiny house is showcased, featuring a rustic wooden design and a welcoming deck. Large windows allow for ample natural light, while a pergola extends over part of the deck, creating a shaded area for outdoor relaxation amidst a lush, green landscape.

Tiny home in Kimberley

Hand-Crafted Cabin in Stunning Beaver Valley

Lovingly designed and built tiny house in the heart of the beautiful Beaver Valley. 2 Double beds, small kitchenette, rustic deck & living area with a gorgeous outhouse. The property has extensive edible landscapes & greenhouse filled with seedless grapes & edible perennials. Beautiful views of the escarpment, close to the Bruce Trail & Beaver River access point for canoeing and kayaking. Shop at the achingly charming Kimberley General Store. Close to Blue Mountains, Thornbury & Collingwood

4.99 out of 5 average rating, 162 reviews

The entrance of a yurt is featured, showcasing a wooden deck with a decorative orange door. The circular structure is surrounded by lush greenery, highlighting the natural setting. Soft light filters through the trees, creating a peaceful outdoor environment.

Yurt in Meaford

Quiet Retreat for Two

Spend a starry night in the country with the comfort of a soft bed, a wood stove, and plenty of space both indoors and out. Our yurt is located in a pocket of trees next to rolling farm fields and beautiful conservation land that the Rocklyn creek meanders through. You can prepare your meals in a sweet outdoor kitchen that is entirely screened in- or choose to sit by the fire. Bruce Trail access is just around the corner, and the towns of Meaford and Owen Sound are a short scenic drive away.

Superhost

A bright living area features a gray sofa, two accent chairs in blue, and a wooden coffee table. A retro red refrigerator is positioned in the kitchen space, accompanied by white cabinetry and a modern stove. Natural light enhances the welcoming atmosphere.

Cabin in Southampton

4.79 out of 5 average rating, 146 reviews

Cabin Suite #5 at Driftwood Haus

Pet Friendly! Listen to the waves steps away! All newly renovated with brand new beds and furnishings. Enjoy the freedom. With the second best sunsets in the world according to National Geographic, Southampton is a community on the shores of Lake Huron in Bruce County, Ontario, Canada and close to Port Elgin. It is located at the mouth of the Saugeen River next to the Saugeen Ojibway Nation Territory. We have the most beautiful public beach in Ontario, a natural harbour and 3 lighthouses!

4.93 out of 5 average rating, 237 reviews

The exterior features a well-maintained yard with lush green grass surrounding a tree stump and a fire pit, creating a relaxing outdoor space. A red grill is positioned next to the entrance of the stone-clad house, and string lights add subtle illumination.

Guest suite in Wiarton

Cozy Getaway on the Bruce Trail!

Newly renovated, this spectacular and spacious two floor unit comes equipped with everything you need for a perfect getaway to the Bruce! This 3 acre property is conveniently located on the Niagara Escarpment with access to the Bruce Trail through the backyard, Only a 5-minute walk to downtown Wiarton or Georgian Bay. A 20-minute drive from Sauble Beach, and only 45 minutes to Tobermory. You won’t need to travel far from this central location to enjoy all the beauty this area has to offer!

4.95 out of 5 average rating, 175 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

Superhost

An aerial view of the tiny house surrounded by lush greenery and trees. The rustic wooden structure features a slanted red roof and an inviting porch area with seating. A clear view of the grassy land leads to the house, emphasizing its quaint and natural setting.

Tiny home in Meaford

4.85 out of 5 average rating, 392 reviews

Tiny Home Nestled between Thornbury & Meaford

Tinyhome situated 10 min to Thornbury and Meaford, and 20 min from Blue Mountain Village, nestled a country/residential area so it is quiet and dark at night. Has all the basic comforts including spacious 3 piece bathroom. Close drive to beaches and many hikes and cross country ski trails in the area. It is also a 15 minute drive from Beaver Valley Ski Club and a number of different cideries. Shared heated pool available for the summer months. Window Aircon/pool opens end of May or June.

4.96 out of 5 average rating, 250 reviews

A serene outdoor space features four wooden chairs arranged around a fire pit on lush green grass. Behind, two vibrant autumn trees stand beside a tranquil lake, framed by a white fence and scenic hills in the background.

Guest suite in Kimberley

"Wine Down" in Scenic Grey Highlands

Join us at “Wine Down”, our beautiful property located on the highlands of the Beaver River Valley, just minutes away from all that Georgian Bay and the Blue Mountains have to offer. It is a very private 1 acre property with an incredible view of water, escarpment and wildlife. Enjoy more than 1,000 sq. ft. of living space including beds for 5, fully equipped kitchen, dining area, living room with large screen TV and full bathroom. Your hosts live on sight in the main level of the house.

4.9 out of 5 average rating, 160 reviews

A spacious living area features large floor-to-ceiling windows offering unobstructed views of Lake Huron. Natural light fills the room, highlighting a mix of seating options and decorative elements. Outside, a private deck and dock can be seen, surrounded by trees and garden space.

Cottage in Lion's Head

Prime Lakefront Tamarack Island Sta-2024-297

Beachfront property on Lake Huron. Great view of sunrise over the lake as cottage is facing east. At night there are amazing reflections of a full moon over the lake as well. Has a large deck and dock. Beautiful garden. This property is in a prime area on Tamarac Island in Stokes Bay. 1500 square feet with loft and windowed porch. Loft has huge desk and pull out bed if needed. Excellent swimming as on the main bay area with deep and warm waters. Back door camera in tree by parking.

4.94 out of 5 average rating, 757 reviews

A serene backyard features a glowing hot tub and a cozy fire pit surrounded by colorful chairs. Soft string lights create a warm ambiance against the night sky, highlighting the green lawn and wooden fencing that offers privacy.

Guest suite in Kimberley

The Post Office Motel & Spa in the ❤️ of Kimberley

*NEW HOT TUB* Located in the center of Kimberley downtown, a scene straight out of a hallmark movie. Watch the seasons come & go while taking in mtn views and soaking in the hot tub as stars line the night sky.Enjoy marshmallows by the 🔥, amidst this whimsical fortress.Walk to the General Store pick up fresh baked goods and breakfast supplies. Then the dinner choice is yours; Hearts Tavern or Justin’s Oven both just steps away. Bruce trail access at the door. The perfect slow down🌿

4.92 out of 5 average rating, 265 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

4.91 out of 5 average rating, 162 reviews

The exterior of a Mongolian yurt is showcased, featuring a sturdy wooden door with glass panels and a welcoming entrance mat. The yurt is surrounded by lush green grounds, indicating a serene rural setting.

Yurt in Priceville

Green Mongolian Yurt on Biodynamic Farm and Spa

The yurt is located on our 200 acre biodynamic farm in beautiful West Grey. Guest are welcome to walk around the property and enjoy being in nature. A cozy insulated space available all year round. This accommodation is rustic with newly constructed washroom facilities near by. A Farm experience is also available. Snowshoeing or skiing trails are nearby or on the farm. Spa (hot tub and sauna) is available for private booking for 2 people for a $125 extra fee

4.88 out of 5 average rating, 337 reviews

A log cabin interior is showcased, featuring warm wooden walls and a cozy seating area. A fireplace is centrally positioned, with a small table nearby. A television is visible, and large windows allow natural light to flood the space, while a loft area is seen above.

Cabin in Owen Sound

Heritage Reflections Guest House

Our place is perfect for someone looking for quiet, private place for a getaway. It is close to the Bruce Trail for hiking and Sauble Beach. We also are close to the Georgian Bluffs rail trail for cycling and hiking. Our guest house is great for couples, solo adventurers, and business travelers. We are a rural property with extensive gardens that you are welcome to explore and enjoy.

Popular amenities for Lion's Head 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, 137 reviews

A charming wooden cabin stands surrounded by lush green farm fields. Two light-colored chairs are positioned on the porch, providing a welcoming touch. The cabin features large windows and a unique circular entry, complemented by the vibrant greenery of trees and crops nearby.

Tiny home in Kimberley

Boho Beaver Cabin 1 with saltwater hot tub

4.95 out of 5 average rating, 467 reviews

The spacious bedroom features a king-sized bed adorned with decorative pillows, complemented by a wooden bedside tray. An armchair occupies one corner, with a desk and paddles adorning the wall. Floor-to-ceiling windows illuminate the room, while exposed wooden accents add a rustic touch.

Flat in Wasaga Beach

The Upper Deck

4.98 out of 5 average rating, 106 reviews

The striking facade of the modern lake house is framed by lush greenery, showcasing large windows and a unique architectural design. A custom pickleball court is visible in the foreground, bordered by flower planters, enhancing the outdoor environment.

Cottage in Meaford

Bayview Oasis: Luxe Lakeside Escape w/ Pickleball

Tiny home in Horning's Mills

A wooden bunkie is set among tall trees, featuring a spacious deck surrounded by a railing. A barbecue unit is positioned on the deck, and a rustic charm is evident in the structure with its natural wood finish and a sloped roof.

4.91 out of 5 average rating, 182 reviews

Pine River Bunkies: Owl’s Roost Off Grid Cabin

A modern living area features a cozy brown leather sofa complemented by black accent pillows. A large flat-screen TV is mounted above a fireplace, and a wooden coffee table displays a decorative tray. Natural light streams through sliding glass doors leading to a patio area.

4.88 out of 5 average rating, 266 reviews

Northern Peaks – Ski In/Out • Hot Tub • Shuttle Ac

4.97 out of 5 average rating, 117 reviews

A welcoming entryway features dark wood paneling and a rustic wooden bench. A framed sign labeled 'Yellow Brick' is displayed prominently on the wall. Decorative plants are placed in woven baskets, adding natural elements to the space.

Home in Mount Forest

The Yellow Brick Guest House

4.81 out of 5 average rating, 109 reviews

A private cedar hot tub is surrounded by tall trees, providing a secluded retreat. Bubbles rise from the water's surface, with a rubber duck floating peacefully. Snow is visible on the ground, creating a serene winter atmosphere.

Cottage in Tiverton

Lake Huron Sunsets at the A-Frame | Cedar Hot tub

Tiny home in Williamsford

An outdoor area showcases a covered hot tub surrounded by wooden lattice. Soft lighting highlights the structure, creating a cozy ambiance. Adjacent is a newly constructed outdoor shower house made of wood, designed for privacy and comfort.

4.95 out of 5 average rating, 238 reviews

Tiny Home Camping for 2 with Hot Tub & Outhouse

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 159 reviews

A winding path is framed by tall trees, leading to a rustic cabin nestled among the forest. Lush greenery flanks the path, creating a serene and secluded ambiance, inviting exploration into the natural surroundings.

Tiny home in MONO

Whispering Pines Cabin in Woodland Acres

4.95 out of 5 average rating, 173 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, 104 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

4.92 out of 5 average rating, 119 reviews

An open-concept living area is visible, featuring two aqua blue chairs with decorative pillows. The kitchen, equipped with modern appliances in sleek cabinetry, is situated in the background. A staircase leads to another level, while a textured wood accent wall adds warmth to the space.

Flat in Meaford

"Bike" at Hills | Pet-Friendly Stay Near Blue Mtn

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

5 out of 5 average rating, 232 reviews

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.

Cottage in Tobermory

Luxury Waterfront Cottage in Tobermory

4.97 out of 5 average rating, 162 reviews

A cozy seating area is featured with a spacious gray sectional sofa adorned with decorative pillows. A coffee table sits in front, with magazines and a remote casually placed on it. A lamp and a window provide soft lighting, enhancing the comfortable space.

Loft in Neustadt

Cozy Loft at Carrick Creek Farmstead

4.95 out of 5 average rating, 253 reviews

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.

Home in Tobermory

Lakeside Lounge

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, 180 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

4.92 out of 5 average rating, 117 reviews

A swimming pool is surrounded by a spacious patio, featuring lounge chairs for relaxation. The sleek water reflects sunlight, creating a serene atmosphere. Lush greenery and trees provide a natural backdrop, while a shed sits nearby, offering additional outdoor storage.

Cottage in Meaford

Woodski Retreat w/Heated Pool on 3+ Private Acres

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.

4.96 out of 5 average rating, 224 reviews

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

4.99 out of 5 average rating, 149 reviews

A spacious outdoor area features a picnic table and multiple lounge chairs arranged on well-maintained grass. The wooden structure in the background has large windows, adorned with awnings, and is surrounded by greenery under a clear blue sky.

Farm stay in Markdale

Experience Country Living at Firefly Ridge

Townhouse in Blue Mountain Resort Area

An open concept living and dining area features a comfortable grey sectional sofa and two circular coffee tables on a textured area rug. The kitchen bar is equipped with four high-backed chairs. Large windows allow natural light to illuminate the space, with views of lush greenery outside.

4.94 out of 5 average rating, 535 reviews

3BR Sierra Scandi Chic - Closest to Village

4.84 out of 5 average rating, 193 reviews

A rustic cabin is nestled among towering trees, featuring a sloped metal roof and wooden door. A table with benches is positioned in front, accompanied by two Muskoka chairs. Gravel pathways lead to the cabin, enhancing its secluded ambiance.

Hut in Owen Sound

Harper Cabin

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, 310 reviews

Cozy Studio Mountainside stay in Blue Mountains