
Holiday rentals in Chesley
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Top-rated holiday rentals in Chesley
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Secluded 4 bed cabin on a river w/ 85-acres.
Cabin on a hill along the Saugeen River beside 700 acres of trails. SKI-IN/OUT or Snowplow cost split 50/50 between guest/host NEW washroom and deck! 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. 6 guests max! Camera in the driveway. More than 6 people are billed as a separate cost, DOUBLING the cost of your booking

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.

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.

Kimberley Creek Cabin
Kimberley Creek Cabin is located in Kimberley, Ontario on a 2 1/2 acre lot surrounded by an old growth forest with a stream running through the property. If you are looking to connect with nature and you enjoy upscale facilities, then this special vacation spot gives you the best of both worlds. Nightly rate includes HST. We are close to hiking, cycling, canoeing, golfing, winter sports, spas, art studios, and fine dining, or simply relax by the firepit or on one of two private decks.

The Post Office Motel & Spa in the ❤️ of Kimberley
*NEW HOT TUB* Located in the center of Kimberley downtown, a scene straight out of a hallmark movie. Watch the seasons come & go while taking in mtn views and soaking in the hot tub as stars line the night sky.Enjoy marshmallows by the 🔥, amidst this whimsical fortress.Walk to the General Store pick up fresh baked goods and breakfast supplies. Then the dinner choice is yours; Hearts Tavern or Justin’s Oven both just steps away. Bruce trail access at the door. The perfect slow down🌿

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.

Lambton Place
LOCATION! LOCATION! LOCATION! Country charm meets urban chic in this stylish three-room suite in 100-year-old house. One block from the beach, one block from downtown shopping, restaurants and pubs. 1) Extra large bedroom, with closet, bureau, king bed; 2) Luxurious, four-piece, ensuite bathroom, with soaker tub, walk-in shower; 3) Sitting room with Wi-Fi, Smart-TV, cable; couch, chair, coffee-maker and small fridge. No kitchen.

The Beach Button
Cute as a Button, this cozy home inspired by beach house vibes is nestled in the quaint town of Meaford. This town offers some of the most amazing waterfront to explore! 2 minutes east is a spacious public beach, 2 minutes towards the west is the beautiful Harbor or step out the door and enjoy a 3min walk down to the lake! This property is also located a scenic 25min to the famous Blue Mountain Ski Resort! and Scandinave Spa!

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.

Forest Dome
This is an air b&b you'll definitely remember. Experience the magical feeling of waking up among the trees and birds. Feel the exhilaration of taking an outdoor shower. Enjoy the crackling fire and take the time to dream again. Nature, art, waterfalls and trails are all just outside your doorstep. Try our available snowshoes to explore even further! You don't want to miss this peaceful retreat.
Popular amenities for Chesley holiday rentals
Other great holiday rentals in Chesley

The Saloon Cabin

From A to Zen - a refined glamp

Pine Villa-Mediterranean Cottage with Hot Tub

Family Cottage On Quiet Lake w/ Shallow Entry

Walkerton Sauna Suite

The Red Roof Retreat

Smokey Creek Reminisce & Sauna

Elderado A-Frame Chalet | 25-Acres & Soaker Tub
Destinations to explore
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