Holiday rentals in Chesley Lake

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Top-rated holiday rentals in Chesley Lake

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Guest favourite
Home in Meaford
4.87 out of 5 average rating, 524 reviews

Beach House Hideaway by Post Office Motel *HOT TUB

This beach house was designed with relaxation and the enjoyment of togetherness in mind. Let your worries melt away as you slip into the warmth of this water side hot tub featuring stunning view across Georgian Bay and up the mountain side, as fresh snow falls around you. The open concept design makes this the perfect place to gather with family and friends w/ walkout waterfront patio and dock access for swimming. 2 min to downtown Meaford, 20 min to Blue Mtn, 1.5 hrs to Tobermory. Hiking Trails

Guest favourite
An aerial view of a lush, green landscape along a tranquil shoreline, showcasing a secluded cove with sandy and pebbly beach areas. The clear turquoise water gently laps at the natural contours of the land, surrounded by dense trees that provide natural shade.
Cottage in Saugeen Shores
4.84 out of 5 average rating, 136 reviews

Secluded 1200' beachfront private 64 acre log home

Welcome to Dragonfly Cove Our log cottage features: *1200 feet of BEACH FRONT *Family-friendly, romantic, retreat *64 private forested acres, secluded cove on Lake Huron *Sleeps 10 (8 adults +2 children on futon) *Full view of lake & sunsets from spacious deck *Full kitchen with antique stove/oven combo *Stunning large glass sunroom *Central AC+heating *Gas+wood fireplaces *Bruce Tel internet *6 person hot tub *Firepit *2 kayaks *3000 acres of manicured trails at McGregor Point Provincial Park

Guest favourite
A charming modern cottage is set against a backdrop of lush greenery and clear blue skies. The exterior features large glass windows and a sloped roof. A patio area with natural stone and comfortable outdoor seating is highlighted, providing a welcoming space to enjoy the views.
Cottage in Meaford
4.91 out of 5 average rating, 206 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
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, 173 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
Two glasses of rosé wine sit on a decorative table, capturing sunlight against a backdrop of rolling hills. The landscape features vibrant autumn foliage in shades of orange and yellow, with a clear blue sky and wispy clouds visible above.
Place to stay in Chatsworth
5 out of 5 average rating, 126 reviews

Secluded Cabin overlooking Valley.

Our comfy one-room cabin sits on the edge of 40 wooded acres, overlooking a pastoral valley. Enjoy a relaxing breakfast (included) on the deck while taking in the countryside view, and in the evening, lose yourself in the deep, dark, star-studded sapphire sky. A great home base as you experience the area - hiking beaches, waterfalls, cideries, vineyards and wineries. See more things to do at visitgrey. ca. Or stay put and enjoy your secluded getaway. Read a book, take a hike, or have a nap.

Guest favourite
A charming A-frame cabin stands amidst lush green trees, with expansive glass doors opening to a wooden deck. Comfortable seating arrangements are present, complemented by planters filled with blooming flowers, creating a serene and inviting outdoor space.
Place to stay in Southgate
4.99 out of 5 average rating, 281 reviews

Aframe cabin by babbling brook with sauna & hottub

Cabin partially OFF GRID in winter months (Nov 1-May 7) No running water/shower/indoor bathroom at this time. Water is provided with water dispenser/maintained outhouse *Wood hot tub replaced in 2025 with nordic spa *Cabin situated on heavily treed 1 acre property with a creek directly in front of a quiet municipal road *Wood stove remains off-limits during the summer season (June-September). Wood & kindling provided for fall/winter use *No firewood provided for firepit/guests to pick up

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, 187 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
A modern home with a black stone exterior is surrounded by vibrant greenery. A large tree provides shade in the foreground, while a spacious deck features seating options and decorative plants. The two-story structure showcases large windows that invite natural light.
Home in Wiarton
4.97 out of 5 average rating, 192 reviews

Kiss & Bond Water View Colpoys Bay 4 -Seasons

Hello,, I'm the owner of a newly built home, that I hope I will provide first-rate, memorable experiences for my guests, I'm a nurse for over 30 years, and I love to explore. Im an animals lover, I'm also a mother of 3 boys and have been married for 33 years ,being outdoors is one of my favourite activities, snowmobiling, hiking. I've owned our cottage for 10 years and we decided to rebuild , to enjoy the beautiful views of Colpoys Bay and in the back yard the Bruce Pennisula escarpment .

Top guest favourite
The modern tiny home features a black exterior and a large glass front, allowing natural light to illuminate the interior. A simple outdoor seating area with two chairs is visible, surrounded by lush greenery and trees, creating a connection with the serene natural surroundings.
Tiny home in Arthur
4.97 out of 5 average rating, 385 reviews

Luxury tiny home on peaceful country estate

Escape to Heirloom Tiny Home - where macro luxury meets a micro footprint. Nestled on 23 peaceful acres, surrounded by aspen and pine forests, just 10 minutes from the picturesque town of Elora. Wake up to serene pond views as horses and sheep graze in your view. Organic linens, artisanal soaps, and a spa-like bathroom soothe the senses. Cozy up by the indoor fire and gaze at the stars. Enjoy fine dining at the Elora Mill and Spa, enjoy popular shops or hike the Elora Gorge nearby.

Top guest favourite
Cottage in Wiarton
4.99 out of 5 average rating, 134 reviews

Waterfront Cottage with Steam Sauna by Bruce Trail

Welcome to this stunning waterfront , cozy ,4 season cottage located on the edge of a cliff surrounded by the lake on one side and Bruce trail on the other. This private oasis is perfect for couples or families w. older kids where you can connect to nature but still stay close to the city. Walking distance to Bruce trail, short drive to Sauble Beach or Wiarton for shopping and dining, 25 min drive to Lions Head, 45 min to Tobermory. It's time to plan your visit to Bruce!!!

Top guest favourite
A colorful rainbow umbrella provides shade over two wooden lounge chairs positioned on a dock overlooking a calm lake. Lush greenery frames the scene, enhancing the peaceful waterside setting under a partly cloudy sky.
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.

Luxe
Cottage in Meaford
4.97 out of 5 average rating, 115 reviews

Bayview Oasis: Luxe Lakeside Escape w/ Pickleball

Welcome to Bayview Oasis, our luxurious lake house on Georgian Bay. Enjoy breathtaking water views, a modern kitchen with high-end appliances, a cozy basement with a pool table and bar, and a master suite with top-notch amenities. Outdoors, relax in the cabana with a pizza oven, fireplace, picnic tables, spacious patio, hot tub, and our new custom pickleball court. Whether it's a romantic getaway or family vacation, Bayview Oasis is the perfect retreat.

Popular amenities for Chesley Lake holiday rentals

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