Vacation rentals in Chepstow

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Top-rated vacation rentals in Chepstow

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Guest favorite
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, 518 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 favorite
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, 122 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 favorite
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 favorite
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, 165 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 favorite
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 favorite
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, 182 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 favorite
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, 377 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.

Guest favorite
The striking facade of the modern lake house is framed by lush greenery, showcasing large windows and a unique architectural design. A custom pickleball court is visible in the foreground, bordered by flower planters, enhancing the outdoor environment.
Cottage in Meaford
4.97 out of 5 average rating, 114 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 favorite
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, 191 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 favorite
An open-concept living and dining area features hardwood floors and large windows providing ample natural light. A comfortable sectional sofa and coffee table are situated in the foreground. The dining table, accommodating multiple guests, is visible in the background near the kitchen.
Home in Port Elgin
4.93 out of 5 average rating, 107 reviews

The Clubhouse - Welcome to Port Elgin, Ontario.

A true BEACH TOWN experience! The Clubhouse in PORT ELGIN has: - Beautiful private backyard with firepit, upper and lower decks - 4 bedrooms w/ queen beds - 2 full bathrooms - 3 parking spots - 8-person dining and games table - foosball table - a home theatre w/ Netflix You will be: - 10 min WALK from Port Elgin beaches, downtown shops & pubs - 90 mins from The Grotto (Tobermory) - 40 mins from Sauble Beach No smoking, pets or parties please.

Top guest favorite
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 favorite
Guesthouse in Neustadt
4.93 out of 5 average rating, 410 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!

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