Holiday rentals in Chesley

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

Secluded 4 bed cabin on a river w/ 85-acres.

Cabin on a hill along the Saugeen River beside 700 acres of trails. NEW washroom and deck with impressive views! This is a family cabin and not a destination for parties. STARGAZERS: Low light pollution. SNOMOBILE trails next door! HIKERS: public trails: Brant Tract. FISHING: On the Saugeen. HUNTERS: 85 acres of Sugarbush. (Must declare prior.) 6 guests max! Camera in the driveway. More than 6 people will be billed as a complete separate cost, essentially DOUBLING the cost of your booking.

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.

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.

Aframe by babbling brook with sauna & hot tub

Amenities: sauna/hottub/record player/projection tv. Nov 1 to May 8 the cabin is partially OFF GRID- No running water/shower/indoor plumbing at this time. Water is provided with water dispenser//outhouse cleaned between guests 15ft from cabin. Sauna available yr round Cabin heated by wood stove in the winter months and supplemented with a mini split heater. Firewood/kindling provided. Summer/fall 2025 there may be some construction noise during your stay due to development in the area.

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 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. (Note this is not on the same property as nearby Airbnb "private farmhouse" listing.)

Tiny A-Frame near the Bruce Trail

Find yourself nestled among white pine trees just steps off the Bruce Trail! This tiny A-Frame is 100 sq.ft providing enough room for cozy comfort. The cabin is equipped with 2 stackable twin beds converting into a queen bed when desired. Our amenities contain all the essentials, including a BBQ, drinking and dish water, and an outhouse with a composting toilet. Centrally located to Old Baldy Lookout, Beaver Valley, Blue Mountain and Duncan Caves. The perfect spot to relax and unwind!

The Cozy on Colborne

Beautifully renovated home combining 1940’s charm and character with carefully curated finishes just steps from downtown Walkerton. Whether you are in town for business or pleasure you will find everything you need and more here. Sleeps 6 comfortably making it great for families or small groups. It features a fully equipped kitchen and spacious deck located right off the kitchen complete with a BBQ, fire-table, lounge furniture and dining table perfect for enjoying a summer evening.

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!