Holiday rentals in Chepstow

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Top-rated holiday rentals in Chepstow

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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, 496 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

Top guest favourite
A charming stone house is set against a backdrop of lush greenery. The facade features large windows and a welcoming porch. A well-kept lawn leads to the entrance, offering a serene view of the surrounding trees.
Cabin in Arthur
4.99 out of 5 average rating, 408 reviews

The Stone Heron

Welcome to the Stone Heron, a diamond in the country side! An hour from Toronto.Check out our insta-gram :thestoneheron. Small stone house completely reno'd!Large master bedroom, gorgeous bathroom 2nd BR bunk beds w/game table downstairs a pool table & darts. DVD, TV wii. Entire home is yours to use, its private, nestled into a hillside covered in periwinkle -nature your only neighbour! Large pond walking trails, wildlife, unplug relax and enjoy!Star filled nights amazing sunsets. Pet friendly

Top guest favourite
The exterior of the modern home is shown at dusk, with warm light glowing from windows. A circular fire pit is surrounded by wooden Adirondack chairs, and the lawn is well-maintained. The covered patio is visible, providing ample space for outdoor seating.
Cottage in Kincardine
4.99 out of 5 average rating, 118 reviews

Kinloft Cottage!

Welcome to the gorgeous beaches of Kincardine, Ontario! Have fun with the whole family at this 4 year old, custom built home! A short walk to the stunning sandy beaches and famous sunsets of Lake Huron (about 9 minute walk) may just have you falling in love with this quiet and peaceful town of Kincardine! A friendly and welcoming community, local dining and quaint shops await you! We are super excited to host you and your family! Great for Contractors or Executives too - 20 min to Bruce Power!

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, 160 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
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
4.98 out of 5 average rating, 323 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.

Guest favourite
Cottage in Walkerton
4.87 out of 5 average rating, 104 reviews

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.

Top 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, 278 reviews

Aframe cabin by babbling brook with sauna & hottub

Cabin is partially OFF GRID in winter months (Nov 1-May 8) No running water/shower/indoor bathroom at this time. Water is provided with water dispenser/maintained outhouse Sauna & jacuzzi tub available yr round. Note: Wood hot tub replaced in 2025 with jacuzzi spa Cabin heated by wood stove in the winter months and supplemented with a mini split heater. Firewood/kindling provided Cabin situated on heavily treed 1 acre property with a creek directly in front of a quiet municipal road

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 *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

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, 367 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 cozy living and dining area is featured, with a round glass table surrounded by four black chairs. A television is positioned against the wall next to a comfortable armchair. A lamp provides warm lighting, while decorative items adorn the walls.
Flat in Clifford
4.9 out of 5 average rating, 104 reviews

Lovely 1 - bedroom apartment. Free parking on site

This lovely, tastefully done basement apartment with separate entrance is close to everything. Suitable for 2 adult and 1 child. There is a roll out twin bed and baby pack and play in the closet in the bedroom. Walking distance to restaurants, shopping and trails. You can hike the trails in Wellington and Grey county, visit shops in surrounding towns, enjoy a festival, tour the farmers markets, go fishing or visit the beaches of Lake Huron and Georgian Bay.

Popular amenities for Chepstow holiday rentals

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