Holiday houses in Chepstow

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chepstow

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Guest favourite
The image captures a tranquil hot tub filled with clear water, positioned on a deck overlooking Georgian Bay. A soft sunset casts a warm glow across the sky, and the silhouettes of a gazebo and dock are visible in the background.
Home in Meaford
4.87 out of 5 average rating, 519 reviews

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

Guest favourite
An aerial view of a lush, green landscape along a tranquil shoreline, showcasing a secluded cove with sandy and pebbly beach areas. The clear turquoise water gently laps at the natural contours of the land, surrounded by dense trees that provide natural shade.
Cottage in Saugeen Shores
4.84 out of 5 average rating, 134 reviews

Secluded 1200' beachfront private 64 acre log home

Welcome to Dragonfly Cove Our log cottage features: *1200 feet of BEACH FRONT *Family-friendly, romantic, retreat *64 private forested acres, secluded cove on Lake Huron *Sleeps 10 (8 adults +2 children on futon) *Full view of lake & sunsets from spacious deck *Full kitchen with antique stove/oven combo *Stunning large glass sunroom *Central AC+heating *Gas+wood fireplaces *Bruce Tel internet *6 person hot tub *Firepit *2 kayaks *3000 acres of manicured trails at McGregor Point Provincial Park

Guest favourite
A cabin is nestled among a lush forest, surrounded by an expanse of green trees. The landscape features varying shades of foliage, with the cabin partially visible from above against the backdrop of the vibrant forest canopy.
Cabin in Paisley
4.89 out of 5 average rating, 123 reviews

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

Top Guest favourite
A modern cottage features a stone exterior with a sloped roof, harmoniously blending into the surrounding forest. A cozy propane fireplace is visible on the patio, which overlooks a gently flowing stream bordered by smooth stones and lush greenery.
Cottage in Southgate
4.99 out of 5 average rating, 166 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.

Guest favourite
An A-frame cottage is surrounded by vibrant autumn foliage, featuring a welcoming front deck with white railings and multiple chairs. Large glass doors invite natural light into the living space, while the steeply pitched roof adds to the rustic charm of the structure.
Cottage in Blyth
4.97 out of 5 average rating, 326 reviews

Up The Creek A-Frame Cottage

Relax in an A-frame Cottage over looking a stocked trout pond surrounded by trees. 20 acres of trails. Fish swim, kayak or canoe in the pond or creek. Watch the ducks, frogs, herons, birds, turtles & a variety of wildlife. Enjoy the stars & roast marshmallows at the camp fire. Fully stocked kitchen, BBQ, wood stove, fire pit and 3 piece bathroom. Wood and linens supplied. Ninja course, water mat & trampoline for your use. Groups welcome, extend your group send your request for more info.

Top Guest favourite
Two glasses of rosé wine sit on a decorative table, capturing sunlight against a backdrop of rolling hills. The landscape features vibrant autumn foliage in shades of orange and yellow, with a clear blue sky and wispy clouds visible above.
Place to stay in Chatsworth
5 out of 5 average rating, 124 reviews

Secluded Cabin overlooking Valley.

Our comfy one-room cabin sits on the edge of 40 wooded acres, overlooking a pastoral valley. Enjoy a relaxing breakfast (included) on the deck while taking in the countryside view, and in the evening, lose yourself in the deep, dark, star-studded sapphire sky. A great home base as you experience the area - hiking beaches, waterfalls, cideries, vineyards and wineries. See more things to do at visitgrey. ca. Or stay put and enjoy your secluded getaway. Read a book, take a hike, or have a nap.

Top Guest favourite
The entrance of a yurt is featured, showcasing a wooden deck with a decorative orange door. The circular structure is surrounded by lush greenery, highlighting the natural setting. Soft light filters through the trees, creating a peaceful outdoor environment.
Yurt in Meaford
4.99 out of 5 average rating, 185 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
The modern tiny home features a black exterior and a large glass front, allowing natural light to illuminate the interior. A simple outdoor seating area with two chairs is visible, surrounded by lush greenery and trees, creating a connection with the serene natural surroundings.
Tiny home in Arthur
4.97 out of 5 average rating, 379 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
A unique double A-frame house is framed by lush greenery, with a spacious driveway leading to the entrance. The structure features a combination of wood and stone elements, while flower beds with emerging blooms add color to the natural surroundings.
Cottage in St. Jacobs
4.99 out of 5 average rating, 192 reviews

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.

Top Guest favourite
A welcoming front porch features two red Adirondack chairs flanking a vibrant potted plant. Surrounding the patio, a garden is landscaped with various colorful flowers and greenery, creating an inviting outdoor space. A path leads to the entrance of the house.
Apartment in Kincardine
4.94 out of 5 average rating, 536 reviews

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.

Top Guest favourite
Guesthouse in Neustadt
4.93 out of 5 average rating, 411 reviews

Bunkie in the Country

Now Open! Welcome! 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!

Top Guest favourite
A geodesic dome is nestled among trees, featuring multiple circular windows that invite natural light. A wooden deck leads to the entrance, where a rustic carving is displayed. A dog sits calmly on the deck, enhancing the serene, natural setting.
Dome in Markdale
4.94 out of 5 average rating, 254 reviews

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 Chepstow holiday rentals

  1. Airbnb
  2. Canada
  3. Ontario
  4. Bruce
  5. Chepstow