Holiday rentals in Chesley Lake

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Top-rated holiday rentals in Chesley Lake

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Top guest favourite
Flat in Owen Sound
4.97 out of 5 average rating, 104 reviews

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.

Guest favourite
Cottage in Sauble Beach
4.94 out of 5 average rating, 138 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

Guest favourite
Two lounge chairs with a light-colored cushion are positioned on a stone patio overlooking Georgian Bay. The shoreline is lined with smooth, rounded stones, and plants are present in the foreground. The warm glow of the sunset reflects over the tranquil water surface.
Cottage in Meaford
4.91 out of 5 average rating, 202 reviews

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.

Top guest favourite
The architect-designed guest house features a striking wooden structure with a sloped roof, surrounded by trees. Large glass walls reflect natural light, and an expansive deck extends out, providing a space for relaxation. A stone wall borders the landscaped area in front of the house.
Guest house in Wiarton
4.96 out of 5 average rating, 112 reviews

Stunning Lakeside Loft Perched Above Georgian Bay

Architect-designed. Award-winning. Most unique property on The Bruce. Cozy, cool Lakeside Loft Guest House at Cameron Point. Open concept loft-style 2-storey Cabin and Bunky. Glass walls. Spectacular views of the water and bluffs! Summer: Loft + Bunky: 4 BR. Up to 8 guests from July 14. Extra fee for guests 5-8: $100/night pp Modern kitchen. 3-pce bath. Private entrance. Wifi. Winter: 2 BR. Base fee for up to 4 guests. Enjoy Bruce Trail hikes, swimming, kayaking. Chill by the fire!

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, 155 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.

Guest favourite
A covered deck features white patio furniture, including a circular table and several chairs, overlooking serene Georgian Bay. Soft lighting is provided by hanging glass pendant lights. The sandy beach is visible below, with gentle waves lapping at the shore under a partly cloudy sky.
Cottage in Tiny
4.97 out of 5 average rating, 149 reviews

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.

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
4.8 out of 5 average rating, 118 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
Bungalow in Georgian Bluffs
4.98 out of 5 average rating, 146 reviews

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.

Top guest favourite
A cordwood cabin is surrounded by lush forest, featuring a green living roof. The rustic structure has a wooden door and multiple windows, with a small outdoor seating area that includes two chairs and a table. Stacked firewood is nearby.
Cabin in Chatsworth
4.99 out of 5 average rating, 145 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
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
4.97 out of 5 average rating, 107 reviews

Grey Highlands Lodge

Our Lodge is perfect for a quiet get away from everyday life, a tranquil patch of greenery nestled in the escarpment of Beaver Valley. If you’re looking for a place to relax and recharge, a place for solitude and restoration, then the Lodge may be just what you need. Enjoy yoga on the side deck, reading in a hammock beside the stream, or exploring the many hikes and nearby amenities just a stones throw away.

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, 344 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 charming cabin exterior is nestled among tall trees, featuring a gravel patio with a grill and several black chairs. A wood railing surrounds the area, complementing the natural setting and providing a peaceful retreat.
Cabin in Meaford
4.94 out of 5 average rating, 155 reviews

Minniehill A-Frame

Designed as a tiny home with everything you need, this semi off-grid cabin is tucked away in Minniehill, Meaford, Ontario. Minutes from beautiful Georgian Bay, down the road from the Bruce Trail hiking entrance, local public and private ski hills, and some of Ontario's best restaurants, while feeling like you've left the rest of the world behind.

Popular amenities for Chesley Lake holiday rentals

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