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Top Holiday Rentals in Chepstow

Our top choices for Chepstow holiday rentals

One-of-a-kind cottage steps from Lake Huron!

10.0 out of 10, Exceptional, (14)
"Carol and Laura went above and beyond to create this amazing oasis! Thank you!"
One-of-a-kind cottage steps from Lake Huron!

Cedarhaven - 2 King beds! Hot Tub, Gas Fireplace

10.0 out of 10, Exceptional, (2)
"This was a great property and the hosts were fabulous! The property was very comfortable and the back yard is beautiful and private. Short drive to town and the public beach!"
Cedarhaven - 2 King beds! Hot Tub, Gas Fireplace

Secluded 3 bedroom bungalow on the Saugeen River with 85-acres.

9.8 out of 10, Exceptional, (19)
"This was a peaceful and private location with a view of the river. Amazing sunrise view every morning from the kitchen table. Really enjoyed our stay. Mark was a great host."
Secluded 3 bedroom bungalow on the Saugeen River with 85-acres.

PIER280 - Lakefront Beauty, Private Lake Access

9.8 out of 10, Exceptional, (6)
"Myself, my husband and our 2 young kids spent an amazing week at Pier280. The view of the late was spectacular! The kids had an amazing time exploring in the rocks and walking into the water. Everything about the cottage was perfect. They even had toys, a children's picnic table and child size chairs on the deck. The area was very quiet and everyone seemed friendly. The cottage was equipped with everything we needed. Really only good things to say! If we don’t purchase a cottage before next...
PIER280 - Lakefront Beauty, Private Lake Access

the Kingfisher Styled for those w discerning taste

10.0 out of 10, Exceptional, (3)
"The cottage was very nice, the outside is brilliant , and the beach is so close. All in all a great place to stay."
the Kingfisher Styled for those w discerning taste

Fully Renovated Cottage on Queen, 3min walk from Beach and Downtown Adventures!

9.8 out of 10, Exceptional, (9)
"We really enjoyed our stay. The place was very nice and as advertised. I would recommend! You'll love the location and the host was really great."
Fully Renovated Cottage on Queen, 3min walk from Beach and Downtown Adventures!

Historic 1 Bedroom Beach Loft - Boutique Styled, Beach, Lake, stay Drifter Lofts

10.0 out of 10, Exceptional, (12)
"This property was a perfect fit. We highly recommend it."
Historic 1 Bedroom Beach Loft - Boutique Styled, Beach, Lake, stay Drifter Lofts

Newly Built 3 Bedroom Cottage, Steps to the Beach

Newly Built 3 Bedroom Cottage, Steps to the Beach

Waterfront Bliss: Firepit & BBQ Cottage R

8.0 out of 10, Very good, (4)
"Clean and comfortable cottage. It was unfortunate that we could not use the paddleboards or kayaks as the water was quite murky, so we didn't want to swim in it, but we would have liked to be on the water. We chose this cottage specifically because we thought we would be able to access the lake. "
Waterfront Bliss: Firepit & BBQ Cottage R

Stoney Island Sunsets. Blue Nugget is located on the sandy shores of Lake Huron.

10.0 out of 10, Exceptional, (10)
"Just an overall excellent experience at this beautiful property and we are looking forward to returning next year ,,hosts are extremely helpful and accommodating,,"
Stoney Island Sunsets. Blue Nugget is located on the sandy shores of Lake Huron.

Modern Classic *LakeViews*

10.0 out of 10, Exceptional, (2)
"Beautiful sunsets"
Modern Classic *LakeViews*

The Chapel Retreat Su

10.0 out of 10, Exceptional, (3)
"Property was beautiful and clean and had everything we needed. It was perfect for a weekend away with the boys "
The Chapel Retreat Su

Historic 2 Bedroom Beach Lofts - Boutique Styled, Beach, Lake, stay Drifter Loft

10.0 out of 10, Exceptional, (2)
"Great place to stay at for a family to explore Kincardine!"
Historic 2 Bedroom Beach Lofts - Boutique Styled, Beach, Lake, stay Drifter Loft

Two bedroom river side apartment with large private yard

10.0 out of 10, Exceptional, (7)
"Great property with all you would need. Quiet and peaceful along the river. "
Two bedroom river side apartment with large private yard

Scenic Waterfront Cottage Retreat - Firepit & BBQ

Scenic Waterfront Cottage Retreat - Firepit & BBQ

Peabody Log Cabin - Three Bedroom Cottage, Sleeps 8

8.0 out of 10, Very good, (1)
"Great location to paddle to/from on the North Sauble River. Take ear plugs as the road is noisy at times. Bbq was discussing, dont plan on using it"
Peabody Log Cabin - Three Bedroom Cottage, Sleeps 8

"stunning Serenity Cove On The Lake Cozy Cottage"

2.0 star property
"stunning Serenity Cove On The Lake Cozy Cottage"

Escape the city and enjoy beautiful, Lake Huron sunsets!

10.0 out of 10, Exceptional, (7)
"The cottage was super cute and cozy, we enjoyed the view of the lake and our comfortable sleeps. Would llove to come back for another stay!"
Escape the city and enjoy beautiful, Lake Huron sunsets!

Relaxing retreat with active options: Modern Bungalow near trails and park

10.0 out of 10, Exceptional, (2)
"Great location."
Relaxing retreat with active options: Modern Bungalow near trails and park

The GOAT Lakehouse

The GOAT Lakehouse
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chepstow Hotel Reviews

Find out more about Chepstow

Find out more about Chepstow

Everything you need to know about Chepstow holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chepstow holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chepstow holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chepstow holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chepstow. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chepstow holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chepstow holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chepstow rentals

At Expedia, we put the best Chepstow holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chepstow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chepstow holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chepstow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Chepstow?

Yes, there are holiday rentals close to the most popular sights in Chepstow, or you can select a more secluded option if you're looking for a relaxing stay. Chepstow is known for its local tours.

What are some of the best holiday rentals that Chepstow has to offer?

Secluded 3 bedroom bungalow on the Saugeen River with 85-acres.: This holiday home rental outside of Chepstow is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Chepstow?

While exploring the area, visit family-friendly sights like The Huron-Kinloss Ice Cream Trail, or get outside and enjoy nature at Marl Lake. Bruce County Public Library - Cargill Branch and Lake Rosalind are a couple of places you'll find in the wider area.

What’s a holiday rental in Chepstow like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chepstow. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a small group gathering.