Vacation rentals in Lion's Head

Private with Self Check-in Bright & Modern Comfort

License: STR2025-9250261010 Welcome to our bright and clean one-bedroom suite ideal for singles, couples, or small families. Walking distance to the Bruce Trail, a short drive to parks, beaches, and lakes; and a good home base to explore the Bruce Peninsula and Tobermory. A comfortable queen size bed in the bedroom with a selection of bedding and pillows. Fully equipped kitchen, modern bathroom, full suite of TV streaming with high-speed internet. Residential area on the west side of town.

Trails End Family Friendly Beach House

Inviting couples and families looking for a relaxing vacation, enjoying beach days, scenic hikes, and stargazing nights. This 3-bedroom beach house is just one street from the sandy beach and playground. Sip your morning coffee on the deck, BBQ in the evenings, and end your day roasting marshmallows at the backyard fire pit under magical dark skies. Hike to the famous lookout. Walk to shops, restaurants, and groceries in minutes. Perfect location for daytripping around the Bruce Peninsula. ✨

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

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.

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

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.

Whiskey Harbour Lakehouse Waterfront

Escape to Whiskey Harbour Lakehouse—your dream waterfront retreat on the Bruce Peninsula. This luxurious timber-frame cottage on Lake Huron blends rustic charm with modern comforts: vaulted ceilings, a stunning Muskoka room, lakefront views, and space for couples, families and nature lovers. Explore turquoise waters, star-filled skies and cozy up fireside after a day of adventure. Ideal for romantic getaways, family escapes and unplugged stays in every season.

A Naturalist's Paradise - Shepard Lake waterfront

Located on a tranquil, private, inland lake-base of the Bruce Peninsula: Spacious suite (lower level of bungalow-one unit, no shared spaces), perfect getaway for outdoor enthusiasts. Private location with secluded sitting areas, firepit, yard & dock. Boats are exclusive for guest use. Enjoy fishing/bird watching. Fabulous hiking trails & beautiful beaches for swimming just minutes away. Close to golf courses. Relax on the dock, read, BBQ & enjoy campfires.

Lion's Head Bahay

This 2-bedroom apartment above an old Ontario farmhouse sits on a half-acre lot with award winning gardens. It has a separate entrance providing a private getaway. It is a great place for staycation, or as a work-from-home alternative, or for families. It is situated in downtown Lion's Head, steps from everything: stores, shops, restaurants, pub, LCBO, beach, marina, children's park, and Bruce trails. NEW in 2024: air-conditioning.

"Paddle" at Hills | Scenic Escape Near Blue Mtn

Welcome to Hills! Once known as Hill's Dairy in Meaford, this historic building has been converted into four rental units with an adventure shop. Steps to downtown Meaford, and minutes to Georgian Bay, Georgian Trail cycling route, the infamous Trout Hollow Trail, shops and restaurants, beaches, and 25 mins from Blue Mountain. This modern suite is the perfect year-round getaway spot to unwind after a day of exploring the area.

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.

Stone Cottage By Georgian Bay

Cosy and private 2 bedroom Stone Cottage directly across from Georgian Bay. Approximately half an acre with water views from the comfort of your living room. Enjoy the fire pit, bbq, games and everything this cottage has to offer. Walk 1.5 kilometres to town and see the caves from the Niagara Escarpment that are 450 million years old. It’s amazing!