Vacation rentals in Chesley

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

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)

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 Lakeridge House

This new well appointed two storey modern four-season accommodation is the perfect for rest and relaxation. Includes 4 bedrooms with a beautiful master - 3-piece ensuite and a second storey balcony from one of the upper floor bedrooms. The Lakeridge House features a beautiful modern open concept kitchen for making culinary dreams come true. An outdoor sauna, and a cold plunge tank for the perfect wellness retreat. Set back and nestled in the woods for privacy it is the perfect escape.

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.

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.

Pine Villa-Mediterranean Cottage with Hot Tub

Escape to our charming Mediterranean-inspired villa nestled in the serene countryside of Ontario. With minimalist aesthetics, the cottage offers a tranquil retreat for relaxation. Immerse yourself in the natural beauty that surrounds as you unwind on the patio or in the hot tub, or explore the countryside with our complimentary bikes. Inside, enjoy minimalist design, cozy details, and a nostalgic record player—where modern comfort meets rustic charm.

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.

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.

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.