Holiday rentals in Chepstow

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Top-rated holiday rentals in Chepstow

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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, 138 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
4.9 out of 5 average rating, 125 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, 178 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
A charming A-frame cabin stands amidst lush green trees, with expansive glass doors opening to a wooden deck. Comfortable seating arrangements are present, complemented by planters filled with blooming flowers, creating a serene and inviting outdoor space.
Place to stay in Southgate
4.99 out of 5 average rating, 285 reviews

Aframe cabin by babbling brook with sauna & hottub

Cabin partially OFF GRID in winter months (Nov 1-May 7) No running water/shower/indoor bathroom at this time. Water is provided with water dispenser/maintained outhouse *Wood hot tub replaced in 2025 with nordic spa *Cabin situated on heavily treed 1 acre property with a creek directly in front of a quiet municipal road *Wood stove remains off-limits during the summer season (June-September). Wood & kindling provided for fall/winter use *No firewood provided for firepit/guests to pick up

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, 194 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.

Guest favourite
A bright sleeping area features a queen-sized bed with a light blanket and decorative pillows. The blue accent wall adds a calming touch, while soft lighting illuminates the space. Floor-to-ceiling curtains in a coordinating hue frame a window, enhancing the room's natural light.
Flat in Hanover
4.81 out of 5 average rating, 79 reviews

Hanover downtown rental unit with free parking

Enjoy your stay in a renovated bachelor’s apartment in downtown Hanover. This 300 sq ft apartment is located on the second floor of the building. Enjoy a queen sized bed , kitchenette, private bathroom, cable tv, air conditioning, and free wifi. This apartment comes with basic amenities to keep you comfortable during your short term stay. These include microwave, fridge, dishwasher, plates, utensils, cookware, single element cook top, and basic kitchen supplies. No smoking, vaping, or pets.

Top guest favourite
Tiny home in Goderich
4.99 out of 5 average rating, 167 reviews

By the Lake Studio Space w/ Gardens & Hot Tub/Pool

NOTE: these photos do not capture our recent upgrades. We think you'll be delighted! You’ll treasure your time at this memorable place in the heart of Goderich. We have designed the space to enjoy outdoor living but with all the indoor comforts for a beautiful nights sleep and a comfortable stay. We've topped it off with a heated pool and a woodfired hot tub for total relaxation. It's Glamping meets the Spa! All while just steps or pedals away from the beach and the downtown square.

Top guest favourite
A hot tub filled with clear water is positioned in the foreground, with steam rising gently. In the background, a cozy seating area surrounds a fire pit, set against a backdrop of lush greenery and a sunset sky.
Guest suite in Kimberley
4.94 out of 5 average rating, 834 reviews

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🌿

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, 397 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.

Luxe
Cottage in Meaford
4.97 out of 5 average rating, 122 reviews

Bayview Oasis: Luxe Lakeside Escape w/ Pickleball

Welcome to Bayview Oasis, our luxurious lake house on Georgian Bay. Enjoy breathtaking water views, a modern kitchen with high-end appliances, a cozy basement with a pool table and bar, and a master suite with top-notch amenities. Outdoors, relax in the cabana with a pizza oven, fireplace, picnic tables, spacious patio, hot tub, and our new custom pickleball court. Whether it's a romantic getaway or family vacation, Bayview Oasis is the perfect retreat.

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, 199 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.

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
4.95 out of 5 average rating, 262 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

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