Vacation rentals in Chesley

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Top-rated vacation rentals in Chesley

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Top guest favorite

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.

Tiny home in Williamsford

4.95 out of 5 average rating, 232 reviews

Tiny Home for 2. Hot Tub, Outdoor Shower, Outhouse

Experience a unique 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. Feel free to enjoy the campfire pit and all of the extra seating we have added this year. We've got a picnic table, chairs and a sitting area with an outdoor bar. Our place is ATV and snowmobile friendly, ask us for details before bringing them. This holiday rental setup is located on our working hobby farm off a main highway.

Top guest favorite

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

4.98 out of 5 average rating, 167 reviews

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

Guest favorite

A cozy loft bedroom features a spacious bed dressed in soft white and blue linens. Light wood flooring complements the blue and dark walls, while bedside tables with lamps provide gentle illumination. A plush robe hangs nearby, and a small rack holds towels for convenience.

Guest suite in Chatsworth

4.86 out of 5 average rating, 391 reviews

Settler's Loft in Log Home

This charming original log home is set amongst rock fences and mature maples on 80 acres of reforested farmland. This two-storey suite sleeps up to 5 guests, has 2 bedrooms, 4-piece bathroom, kitchenette, living area, deck, & private balcony. Trails for exploring, campfire ring, and large grassy area for outdoor games. Brand new AC system. Very close to OFSC snowmobile trails. (Note - barn access is for weddings only) NO pets >> 40 minute drive to Blue Mountain; 30 minutes to Lake Huron beaches

Guest favorite

A serene lake scene is framed by lush greenery. Reflections of trees and nearby structures can be seen on the calm water surface. The shared outdoor area features a deck that is slightly visible along the shoreline.

Guest suite in Hanover

4.92 out of 5 average rating, 153 reviews

Lorbin Lake Studio suite. Minimum 2 night stay.

Stand alone studio style suite set on a private lake. We offer 2 night minimum stays.The studio suite includes a kitchen and comfortable livingroom. Queen bed ,queen pull out sofa and roll away cot. Playpen available on request. Large shower, gas fireplace and air conditioning . Stroll around the beautiful grounds and enjoy all inclusive canoe,paddleboards and paddle boat with no rental fees. Guest suite also offers wifi and a 52 inch t.v and satellite. Please note we do not have extra fees.

Top guest favorite

An open and airy space features a large harvest table with pink legs, complemented by wooden chairs. A cozy bench is positioned alongside the table. A staircase leads to a loft area, while art supplies and decor are visible throughout the room.

Home in Desboro

4.97 out of 5 average rating, 135 reviews

Forest Loft - Forest, Sauna, Ponds & Stargazing

The “Forest Loft” is a one-of-a-kind space surrounded by the old-growth trees of Kinghurst Forest. The 1,600-square-foot space sleeps up to four and features two Queen-size beds and linens, huge harvest table, indoor kitchenette with a stovetop and fridge, filtered water, shower, propane and wood stove heating, in-door basketball hoop, hammock, picnic table, a commercial grade BBQ, fire ring and access to two beautiful spring-fed ponds. Access to Finnish sauna for four is available on request.

Top guest favorite

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

4.98 out of 5 average rating, 131 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 favorite

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, 156 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 favorite

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

4.96 out of 5 average rating, 246 reviews

"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.

Top guest favorite

A vibrant red cabin is surrounded by lush greenery, featuring a spacious elevated deck. A dining table with six chairs is set under a large umbrella, while a barbecue grill is positioned nearby. Large windows invite natural light into the interior.

Cottage in Elmwood

4.98 out of 5 average rating, 145 reviews

Little Red Cabin on the River

Bright and cozy, open concept cabin retreat overlooking Styx river in beautiful West Grey. Relax next to a quiet river on a large lot with elevated deck, natural wood-burning fire pit and BBQ. This all season get away is 2 hours from Toronto, perfect for small families or a small group. Recently updated, this cabin features simple, modern decor with a fully furnished kitchen for home cooked meals and baking. Also now includes WiFi and an outside wood burning, cedar barrel sauna.

Top guest favorite

A rustic bunkie is nestled among lush trees, featuring a wooden porch with steps leading to the entrance. Two outdoor chairs are positioned beside a circular stone fire pit, creating a relaxed atmosphere for gatherings. A variety of greenery surrounds the area.

Guesthouse in Neustadt

4.93 out of 5 average rating, 399 reviews

Bunkie in the Country

Now open! The bunkie has a great view of the sunrise. It's a quiet rural area (please note it is a GRAVEL road). Good for couples, solo adventurers, hunters, someone looking to be outside of town. The bunkie is located approx. 30 feet behind our home. We have 1 large dog on site (lives in the house). For allergenic reasons and safety of other animals, we do not allow pets. May not be suitable for those with mobility issues (small hill & stairs). The bunkie has heat and A/C!

Guest favorite

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

4.91 out of 5 average rating, 158 reviews

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 outhouse (composting toilets), outdoor showers and wash basin. Farm experience is also available. Snowshoeing or skiing trail are nearby or on the farm. The Spa (hot tub and sauna) is available for private bookings for additional fee.

Top guest favorite

A cozy living room features a teal sofa, a brown armchair, and a wooden television stand. A flat-screen TV is mounted on the wall. A patterned area rug covers the hardwood floor, while a coffee table with a geometric design sits in the center. Natural light enters through a window.

Apartment in Owen Sound

4.96 out of 5 average rating, 157 reviews

Suite on the Creek

Keep it simple at this peaceful and centrally located walkout apartment. The suite backs onto the Niagara escarpment and sections of the Bruce Trail. Though you’ll feel secluded in nature, head out front and you can walk downtown in less than 15 minutes. Rest well in the king-sized bed that looks out onto the walking bridge in the back yard. Enjoy cozy evenings in with a movie and a fire, or relax with a book in your private backyard sitting area.