Vacation rentals in Chepstow

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Top-rated vacation rentals in Chepstow

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Top guest favorite
The exterior of a green-grey one-story apartment is visible, featuring a private entrance and wooden steps. Large windows allow natural light to illuminate the space, while fallen leaves frame the walkway. A small shrub is positioned beside the entrance, enhancing the inviting appearance.
Apartment in Owen Sound
4.97 out of 5 average rating, 104 reviews

Private with Self Check-in Bright & Modern Comfort

License: STR2025-9250261010 Welcome to our bright and clean one-bedroom suite ideal for singles, couples, or small families. Walking distance to the Bruce Trail, a short drive to parks, beaches, and lakes; and a good home base to explore the Bruce Peninsula and Tobermory. A comfortable queen size bed in the bedroom with a selection of bedding and pillows. Fully equipped kitchen, modern bathroom, full suite of TV streaming with high-speed internet. Residential area on the west side of town.

Guest favorite
A stylishly designed entryway features a textured, herringbone-patterned wall in neutral tones. A wooden coat rack with multiple hooks is mounted alongside a door. Stairs lead up to a bright area, illuminated by natural light, enhancing the welcoming feel of the space.
Place to stay in Hanover
4.93 out of 5 average rating, 206 reviews

Single room Queen bed all the right amenities

This stylish place is close to must-see destinations. If you like the outdoors head five miles east to Allan Park. You’ll find hiking trails, snowshoeing, tobogganing and cross country skiing. Four miles south takes you to Saugeen Conservation Centre where you’ll see Swans a swimming and the nature trails will take you to the Sulphur Spring. Hanover’s P&H Centre hosts an indoor pool and ice rink. A short drive gets you to the beaches on Lake Huron. Enjoy horse races in summer and Casino.

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, 155 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.

Superhost
Cottage in Walkerton
4.86 out of 5 average rating, 100 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.

Guest favorite
The cozy bedroom features a spacious bed with a patterned white and yellow duvet. Natural light enters through the nearby window, illuminating the room. A small lamp beside the bed adds soft lighting, while the open doorway reveals a glimpse of the kitchen area.
Cabin in Southampton
4.8 out of 5 average rating, 118 reviews

Cabin Suite #3 at Driftwood Haus

Pet Friendly! Listen to the waves steps away! All newly renovated with brand new beds and furnishings. Enjoy the freedom. With the second best sunsets in the world according to National Geographic, Southampton is a community on the shores of Lake Huron in Bruce County, Ontario, Canada and close to Port Elgin. It is located at the mouth of the Saugeen River next to the Saugeen Ojibway Nation Territory. We have the most beautiful public beach in Ontario, a natural harbour and 3 lighthouses!

Guest favorite
A wooden sign welcomes guests to 'The Cedars,' placed near a grassy area. A small cabin with a blue roof is visible in the background, accompanied by a porch and chairs. Surrounding trees provide a natural backdrop, enhancing the peaceful atmosphere.
Farm stay in Formosa
4.93 out of 5 average rating, 101 reviews

The Cedars

Escape to our neck of the woods and re-connect with nature at "The Cedars". Nestled in the valley on our 75 acre farm, the Cabin has its own fire-pit area, picnic table, chairs, outhouse and acts as a base camp for exploring beautiful Bruce County or relaxing onsite. Experience cows grazing the surrounding pasture fields or enjoy the sounds of the water flowing along the creek. The property offers gorgeous views of the countryside and is located 30 minutes from the beaches of Lake Huron.

Top guest favorite
A cozy seating area is featured with a spacious gray sectional sofa adorned with decorative pillows. A coffee table sits in front, with magazines and a remote casually placed on it. A lamp and a window provide soft lighting, enhancing the comfortable space.
Loft in Neustadt
4.97 out of 5 average rating, 172 reviews

Cozy Loft at Carrick Creek Farmstead

Carrick Creek Farmstead is a sanctuary in the corner of Southeast Bruce County in Ontario. The Farmstead offers you 170 acres of rolling hills, a woodlot and walking trails. The Loft is a suite above our garage. A king bed and pull out sofa bed allow accommodation for 4 adults. The loft has kitchen facilities, shower, television, and air conditioning for the summer. Enjoy a meal on the nearby patio. If you would like to enjoy some prepared food from the Carrick Creek kitchen, just ask.

Top guest favorite
A serene outdoor space features four wooden chairs arranged around a fire pit on lush green grass. Behind, two vibrant autumn trees stand beside a tranquil lake, framed by a white fence and scenic hills in the background.
Guest suite in Kimberley
4.97 out of 5 average rating, 260 reviews

"Wine Down" in Scenic Grey Highlands

Join us at “Wine Down”, our beautiful property located on the highlands of the Beaver River Valley, just minutes away from all that Georgian Bay and the Blue Mountains have to offer. It is a very private 1 acre property with an incredible view of water, escarpment and wildlife. Enjoy more than 1,000 sq. ft. of living space including beds for 5, fully equipped kitchen, dining area, living room with large screen TV and full bathroom. Your hosts live on sight in the main level of the house.

Superhost
A sunset view over Lake Huron is captured, displaying a vibrant array of orange and red hues reflecting on calm water. The horizon is met with silhouettes of distant trees, creating a serene coastal landscape.
Guesthouse in Port Elgin
4.83 out of 5 average rating, 130 reviews

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.

Top guest favorite
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.
Apartment in Clifford
4.9 out of 5 average rating, 103 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.

Top guest favorite
A rustic bunkie is nestled among lush trees, featuring a wooden porch with steps leading to the entrance. Two outdoor chairs are positioned beside a circular stone fire pit, creating a relaxed atmosphere for gatherings. A variety of greenery surrounds the area.
Guesthouse in Neustadt
4.93 out of 5 average rating, 410 reviews

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!

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, 530 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.

Popular amenities for Chepstow vacation rentals

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