Holiday rentals in Chesley Lake

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Top-rated holiday rentals in Chesley Lake

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Guest favourite
A light-filled living area features a comfortable gray sofa and two rattan chairs with cushions. A flat-screen TV is mounted on the wall, and a natural fiber rug lies beneath a white coffee table. Elements of greenery can be seen, adding a refreshing touch.
Cottage in Sauble Beach
4.94 out of 5 average rating, 136 reviews

COMPLETELY RENOVATED cottage -steps from the Beach

Charming coastal cottage, 2 min walk to the beach and 5 to the main strip. This is a perfect beachside retreat, with new flooring throughout, plank ceilings, fully loaded kitchen with SS appliances and quartz countertops, new bathroom, new mattresses... a large fully furnished patio and fire pit. 2.5 hours outside of TO on the shores of Lake Huron - and fully winterized for year-round getaways! AS SEEN IN HOUSE AND HOME MAGAZINE, JULY 2019! FOLLOW US: @amabelbeachhouse * linens not provided

Top guest favourite
Cottage in Wiarton
4.91 out of 5 average rating, 105 reviews

Sunsets & Lake Views in a Spacious Modern Cottage

Escape to a bright, spacious cottage with stunning sunsets and panoramic views of Colpoy’s Bay just outside Wiarton! Perfect for year-round group getaways featuring: 4 king bedrooms, a queen Murphy bed and 3 full bathrooms including a spa-like master ensuite. Enjoy an open-concept layout with a fully stocked kitchen, two large family rooms with Smart TVs, two expansive patios, and a spacious campfire area. Experience the natural beauty of the Bruce Peninsula while relaxing in comfort and style.

Guest favourite
A cozy wooden cabin is nestled in a snowy landscape, featuring a circular wooden door and large windows. Two rustic Adirondack chairs are placed on either side of the entrance, while green wooden trees adorn the exterior, complementing the natural setting.
Tiny home in Williamsford
4.94 out of 5 average rating, 245 reviews

Tiny Home Camping for 2 with Hot Tub & Outhouse

Experience a unique winter camping retreat for two in our wood-stove-heated tiny home. Complete with an outdoor shower, outhouse, covered hot tub, and a propane BBQ for cooking. The campfire pit and picnic table sitting area are open all year. This holiday rental setup is designed for couples and located on our working hobby farm right off a main highway. * Please note, the outdoor shower and bar closes seasonally due to freezing temperatures with no alternative available. Reopens May 2026.

Top guest favourite
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
4.99 out of 5 average rating, 146 reviews

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.

Top guest favourite
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
4.99 out of 5 average rating, 171 reviews

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.

Top guest favourite
The exterior of a two-story house is depicted, featuring a combination of blue siding and brick. Soft illumination highlights the windows, providing a warm glow. A green lawn and a tree are visible in the foreground, alongside a vehicle parked in the driveway.
Home in Southampton
4.95 out of 5 average rating, 136 reviews

Holiday House on Huron

The location is truly special—just a short walk to boutique shops, local cafés, excellent restaurants, and a craft brewery. Whether you're here for the beach, biking the scenic Saugeen Rail Trail, or exploring the charm of small-town life, this is the perfect spot to experience it all. The open concept upper level is designed for gathering, entertaining, or simply unwinding in comfort. Main floor, you’ll find three cozy bedrooms (primary bedroom with ensuite), a full bathroom with bathtub.

Guest favourite
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
4.93 out of 5 average rating, 238 reviews

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!

Guest favourite
The cozy bedroom features a spacious bed with a patterned white and yellow duvet. Natural light enters through the nearby window, illuminating the room. A small lamp beside the bed adds soft lighting, while the open doorway reveals a glimpse of the kitchen area.
Cabin in Southampton
4.79 out of 5 average rating, 111 reviews

Cabin Suite #3 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!

Top guest favourite
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
4.92 out of 5 average rating, 274 reviews

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

Top guest favourite
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
4.99 out of 5 average rating, 143 reviews

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.

Top guest favourite
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
4.88 out of 5 average rating, 340 reviews

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.

Guest favourite
A spacious living area features a comfortable seating arrangement with a dark sofa and rustic coffee table. Light filters through large windows, highlighting a cozy sleeping area with a wooden framed bed adorned with soft pillows. Natural elements create a calming and serene environment.
Cabin in Lucknow
4.91 out of 5 average rating, 232 reviews

Pine Reeve Cabin. Rustic cabin in the woods.

Pine Reeve cabin was once a simple 24x24 hunt shack. A vision and some time has brought it to what it is today. A rustic, quiet getaway to recharge. A 20 minute scenic drive will bring you to numerous beaches along Lake Huron. A few local places worth mentioning in the surrounding area to explore is Goderich, Bayfield, grand bend and Kincardine!

Popular amenities for Chesley Lake holiday rentals

  1. Airbnb
  2. Canada
  3. Ontario
  4. Bruce
  5. South Bruce Peninsula
  6. Chesley Lake