Vacation rentals in Chesley

Single room Queen bed all the right amenities

This stylish place is close to must-see destinations. If you like the outdoors head five miles east to Allan Park. You’ll find hiking trails, snowshoeing, tobogganing and cross country skiing. Four miles south takes you to Saugeen Conservation Centre where you’ll see Swans a swimming and the nature trails will take you to the Sulphur Spring. Hanover’s P&H Centre hosts an indoor pool and ice rink. A short drive gets you to the beaches on Lake Huron. Enjoy horse races in summer and Casino.

Lakefront Family Cottage on Quiet Private Lake

Beautiful and quiet lakefront cottage in Grey County Our serene and charming all season cottage is nestled on a semi-private lake just 2 hours north of Toronto. Enjoy the beautiful nature on this 35 acre property with private trails and stunning lake views. Great for 2 families - sleeps up to eleven! 4 bedrooms (3 Bedrooms and 1 Nursery) and 3 bathrooms. We hope to provide the charm of a traditional cottage but with modern comforts! *Sauna available for additional $50 fee (for wood +cleaning)

A home away from home

Home in new subdivision with finished basement for use to guests for daily, weekly, or monthly stay. Has nice bright windows and floor heated. Large 65" tv with local cable. fiber wifi. Open staircase to upper house but your privacy is much respected . Small appliances provided. Price is per person when booking please add number of guests, queen bed and double bed available in 2 separate bedrooms. couch is available with bedding in bathroom closet this could accommodate the 5th person if need

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.

The Velvet Pier by the Post Office Motel *HOT TUB*

The Velvet Pier is where Georgian Bay’s wild beauty meets the unapologetic glamour of Old Hollywood. Inspired by the romance of the 1950s, this 4 bedroom luxurious waterfront escape is made for champagne sunsets, slow mornings, moonlight swims and picture perfect moments! Perfectly located on the edge of the Dark Sky Light Preserve, stargazing from the hot tub doesn’t get any better. From girls’ getaways to memory-making family escapes, every corner is made for connection and celebration 🩷

Sundance of Blantyre Lodge +Hot Tub +Sauna +Pond

Welcome to Sundance of Blantyre! Step back in time in this historic yet modernized Lodge! This 3600 sq. ft retreat on the Bruce Trail has Breathtaking Valley Views from your own Private Hot Tub & Fire Pit all the Way to Georgian Bay. We invite you to enjoy our truly unique and tranquil getaway with 6 bedrooms + Private Sauna House! With 3 firepits, swimmable/fishing pond, hiking, cross country skiing and snow shoeing + snowmobile/ ATV trail access at your door, Your adventure awaits!

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.

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! 6 guests max! Camera in the driveway. No more exceptions. This is a family cabin. Not a destination for parties. STARGAZERS: Zero pollution SNOMOBILE trails next door! HIKERS: public trails Brant Tract FISHING: On the Saugeen HUNTERS: 85 acres of Sugarbush. Must declare prior. More than 6 people? They are billed as a separate cost, DOUBLING the cost of your booking.

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.

Cedar and Fern Cabin | Private Pond Forest Retreat

Welcome to Cedar & Fern Cabin — a peaceful forest retreat where comfort meets nature, and where your days are shaped by the water, the woods, and the quiet. Designed as an easy escape from the city, it offers the calm of nature without the long, traffic-filled drive to crowded destinations. Whether you’re here for a romantic weekend or a peaceful family getaway, this is a place to unplug, breathe deeply, and truly unwind.

Williamsford Blacksmith Shop

Make some memories at the historic stone blacksmith shop built 1888. Located in Williamsford, Ontario. Conveniently located to the historic sites, waterfalls, the Bruce trail, rail trails for hiking and snowmobiling. Short 20 minute drive to Owen Sound. Sauble Beach 40 minutes. Tobermory drive 1 hr 1/2. Markdale 20 minutes. Enjoy the sites surrounding or a peaceful night by the campfire with campfire wood provided.

The Cozy on Colborne

Beautifully renovated home blending 1940’s charm with thoughtfully curated, modern finishes located just steps from downtown Walkerton. Whether you are in town for work, a quiet stay or a family event, the home is designed to be comfortable, practical and easy to settle into. Features include a fully equipped kitchen, fast reliable Wi-Fi with a dedicated workspace, garage parking for one and onsite laundry.