Holiday rentals in Chepstow

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Top-rated holiday rentals in Chepstow

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Guest favourite

Home in Meaford

4.87 out of 5 average rating, 431 reviews

Waterfront* Hot Tub* - Beachhouse Hideaway *Unique

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

Guest favourite

Cabin in Paisley

4.89 out of 5 average rating, 120 reviews

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.

Guest favourite

Cottage in Meaford

4.92 out of 5 average rating, 183 reviews

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.

Top guest favourite

Cottage in Southgate

4.98 out of 5 average rating, 121 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 favourite

Yurt in Meaford

4.99 out of 5 average rating, 148 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 favourite

Loft in Neustadt

4.97 out of 5 average rating, 152 reviews

Cozy Loft at Carrick Creek Farmstead

Carrick Creek Farmstead is a sanctuary in the corner of Southeast Bruce County in Ontario. The Farmstead offers you 170 acres of rolling hills, a woodlot and walking trails. The Loft is a suite above our garage. A king bed and pull out sofa bed allow accommodation for 4 adults. The loft has kitchen facilities, shower, television, and air conditioning for the summer. Enjoy a meal on the nearby patio. If you would like to enjoy some prepared food from the Carrick Creek kitchen, just ask.

Guest favourite

Place to stay in Southgate

4.98 out of 5 average rating, 260 reviews

Aframe by babbling brook with sauna & hot tub

Nov 1 to early May the cabin is partially OFF GRID- No running water/shower/indoor bathroom at this time. Water is provided with water dispenser//outhouse cleaned between guests. Sauna & roto spa tub available yr round. Pet friendly// 1 dog per booking with pet fee. 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.

Guest favourite

Cottage in Tiverton

4.81 out of 5 average rating, 100 reviews

Lake Huron Sunsets at the A-Frame | Cedar Hot tub

Relax with the family lakeside and among the cedars at this peaceful A-frame retreat on the shoreline of Lake Huron. The door opens up into a large living room and kitchen with a 180 degree view of the lake. An 8-foot island surrounded by bar stools anchors the kitchen. Watch the famous Lake Huron sunsets while having a meal or soaking in the hot tub. Our front is a rocky beach with a fire pit. We swim here with our water shoes. The sandy beach is a 2 mins drive or a 5-10 min bike ride.

Guest favourite

Cabin in Clarksburg

4.96 out of 5 average rating, 109 reviews

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!

Top guest favourite

Tiny home in Arthur

4.96 out of 5 average rating, 303 reviews

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.

Top guest favourite

Guest house in Neustadt

4.93 out of 5 average rating, 390 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 favourite

Cottage in Saugeen Shores

4.83 out of 5 average rating, 127 reviews

Secluded 1200' beachfront private 64 acre log home

Welcome to DRAGONFLY COVE Our log cottage features: • 1200 feet of BEACH FRONT, suitable for swimming & small boats • 64 private acres, secluded cove on Lake Huron • Sleeps 10 (8 adults +2 children on futon) • Full view of lake & sunsets from spacious deck • Fully outfitted kitchen with antique stove/oven combo • Stunning large glass sunroom • Central air conditioning • Gas+wood fireplaces • Starlink high speed internet • 5-6 person hot tub