
Holiday houses in Chepstow
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Top-rated holiday rentals in Chepstow
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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

Valley View Farm Retreat ~ Hiking, Skiing, Pets
Enjoy this unique 4 bedroom Farm House as a gorgeous space to gather with family or friends. -Ideal location to come together, relax, & connect. -Central heat & AC. -Take in the spectacular views of the Beaver Valley. -Explore the Niagara Escarpment and lookouts of the Bruce Trail. -Relax and read by the fireplace. -5 min walk to our swimming pond with dock & beach -Convenient drive to groceries and local villages. -25 min drive to the Blue Mountains. -Reliable, consistent high speed internet.

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.

Classic Cozy Tudor home, a walk away from river
Experience charm at our Tudor-style home in Walkerton. This historic brick residence features original gumwood trim, leaded glass windows, and elegant stone retaining walls. You're steps from downtown restaurants and the Saugeen River's trails perfect for fly fishing and canoeing. Just 30 minutes to Lake Huron. The home shines through all seasons - from snow-covered winter evenings to spring's flowering crabapple blooms. Modern comfort meets historic elegance in this well-maintained retreat.

Holiday House on Huron
The location is truly special—just a short walk to boutique shops, local cafés, excellent restaurants, and a craft brewery. Whether you're here for the beach, biking the scenic Saugeen Rail Trail, or exploring the charm of small-town life, this is the perfect spot to experience it all. The open concept upper level is designed for gathering, entertaining, or simply unwinding in comfort. Main floor, you’ll find three cozy bedrooms (primary bedroom with ensuite), a full bathroom with bathtub.

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.

Rustic Lakeview Cottage, steps to the beach!
The views are fabulous, sunsets like no other. Huge backyard with fire pit and new bbq. The house is well cared for with all the amenities you will need for a great vacation. Just added for 2023 Man Cave in the garage featuring , darts, table hockey and Foosball, play your favorite games while overlooking the lake. Come join us we can’t wait to host you. Early check in on request if possible $100 fee added to your reservation . One pet allowed under 10 lbs for $100 fee for stay .

Cozy waterfront apartment with beach access
Lakeview paradise ! 1 min walk to the beach. Waterfront guest(studio) apartment with a panoramic view of Lake Huron. Enjoy the breathtaking sunset and lake view from couch or bed. Lovely bike and walking trails nearby. 2 bikes and 2 person inflatable kayak available for rental. French press coffee machine, electric kettle, microwave, double hot plate, 3.3 cuft refrigerator + fridger, pots/pans and cutleries. I have camera facing front yard and driveway for your privacy.

The Evelyn Suites - Suite A - Luxury Pied-à-Terre
Hello! We are MacLean & Sarah, owners of The Evelyn Restaurant and The Evelyn Suites. Centrally located in a historic, limestone building on a Main Street in Elora, this beautifully appointed, French modern style, 2 bedroom apartment is within walking distance of everything the village has to offer, including the Elora Gorge, Shops, Restaurants and The Elora Mill & Spa. We look forward to hosting you while you relax and enjoy your stay in our luxurious pied-à-terre!

St. Jacobs Triangle House - Countryside Escape
Welcome to Triangle House, a unique double A-frame situated on a private 1.7 acre lot, fronting on the Conestogo river Only 6 minutes drive from St.Jacobs center, 1.5 hours drive from Toronto, 15 minutes drive from the University of Waterloo and 25 minutes to Elora. Bring the whole family. This 3 bed, 3 bath home comfortably sleeps 6. Soak in the countryside from the sprawling deck and grounds, while enjoying all the comforts of a modern home.

Bunkie in the Country
Now CLOSED until spring 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. For allergenic reasons and safety of 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!

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.
Popular amenities for Chepstow holiday rentals
Other great holiday rentals in Chepstow

Coyotes on 14

Fern Hill Cabin

Etherington Suites- The Victoria Suite- NEW!

Cedarhaven - 2 King beds! Hot Tub, Gas Fireplace

Sauble Shores Waterfront Hideaway

Beach town bungalow

Stone Farm House Spa Retreat

Private Studio Loft Steps to Downtown Elora & Mill
Destinations to explore
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