Chepstow Holiday Rentals

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Holiday Rentals in Chepstow

Cedarhaven - 2 King beds! Hot Tub, Gas Fireplace

Inverhuron
10.0 out of 10, Exceptional, (5)
"What a lovely stay! Our vacation home was so inviting! We were pleased with the exceptional cleanliness, the modern decor and the availability of consumables such as spices, toilet paper, soap, detergent.We’re already talking about a return visit:)Thank you Jennifer for your hospitality!"
Canada
Anna Maria D.
Cedarhaven - 2 King beds! Hot Tub, Gas Fireplace

Newly Built 3 Bedroom Cottage, Steps to the Beach

Inverhuron
Newly Built 3 Bedroom Cottage, Steps to the Beach

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

Kincardine
10.0 out of 10, Exceptional, (13)
"Kincardine is a holiday gem. So nice, so unique, everyone loves it."
Canada
Kenneth S.
Historic 1 Bedroom Beach Loft - Boutique Styled, Beach, Lake, stay Drifter Lofts

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

Kincardine
9.8 out of 10, Exceptional, (11)
"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."
United States
Jason B.
Fully Renovated Cottage on Queen, 3min walk from Beach and Downtown Adventures!

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

Paisley
9.8 out of 10, Exceptional, (22)
"The place is very nice, it is very cozy. The view from the cottage is amazing. Our pets were very happy to run all over the place. We just stay for a couple of days, but would be nice for a larger stay next time."
Canada
Wren Y.
Secluded 3 bedroom bungalow on the Saugeen River with 85-acres.

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

Kincardine
10.0 out of 10, Exceptional, (10)
"Beautiful view of the lake. The cottage is perfect for a weekend getaway. The owners are kind and attentive, the place in clean, comfortable and quiet. My wife and i enjoyed our stay 10/10 would definitely rent again"
Canada
Kelly G.
Stoney Island Sunsets. Blue Nugget is located on the sandy shores of Lake Huron.

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

Kincardine
10.0 out of 10, Exceptional, (5)
"We found everything very nice and the extra's were very appreciated and enjoyed. Thank you. We would definitely recommend this place."
United States
mike
Historic 2 Bedroom Beach Lofts - Boutique Styled, Beach, Lake, stay Drifter Loft

Waterfront Bliss: Firepit & BBQ Cottage R

Hanover
8.4 out of 10, Very good, (5)
"The place was beautiful, as was the lake. Everything was provided and made the stay very easy. However, two issues were there. First, I didn’t realize that the one bathroom was connected to one of the bedrooms, and the two single bedrooms were not separated by a door or anything. Obviously not a dealbreaker, but people constantly coming to my room to use the bathroom, especially during the night did get a bit annoying. Secondly, the fire alarm is horrible. It was constantly going off every time...
United States
AamerS
Waterfront Bliss: Firepit & BBQ Cottage R

the Kingfisher Styled for those w discerning taste

Inverhuron
10.0 out of 10, Exceptional, (4)
"The cottage was very nice, the outside is brilliant , and the beach is so close. All in all a great place to stay."
United States
Terry C.
the Kingfisher Styled for those w discerning taste

Modern Classic *LakeViews*

Kincardine
10.0 out of 10, Exceptional, (2)
"Such a great place to have a family reunion. We so loved the beautiful sunsets, the perfect cabin layout for being together and the very attentive host. The cabin was well stocked and met everyone’s needs perfectly. It was a lovely time as we were able to recall past memories of being at the beach as kids - and now create some new special memories too! We will definitely be back!"
Canada
Mary M.
Modern Classic *LakeViews*

Two bedroom river side apartment with large private yard

Wingham
10.0 out of 10, Exceptional, (8)
"Great property with all you would need. Quiet and peaceful along the river. "
Canada
Theresa R.
Two bedroom river side apartment with large private yard

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

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

Twilight Haven – Where Family Fun Meets Lake Life

Kincardine
10.0 out of 10, Exceptional, (3)
"Great location. Walking distance to the beach. Loved the decor. Clean and welcoming. Responsive host. Had a terrific time and plan to book again for next year. "
Canada
Nancy C.
Twilight Haven – Where Family Fun Meets Lake Life

"stunning Serenity Cove On The Lake Cozy Cottage"

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

Escape the city and enjoy beautiful, Lake Huron sunsets!

Tiverton
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!"
Canada
Ashley M.
Escape the city and enjoy beautiful, Lake Huron sunsets!

Family/pet oriented home close to beaches shopping and cottage country AC Wifi

2.0 star property
Kincardine
Family/pet oriented home close to beaches shopping and cottage country AC Wifi

The GOAT Lakehouse

Kincardine
The GOAT Lakehouse

The Chapel Retreat

Bluevale
The Chapel Retreat

Cottage Rental close to lake Huron beach!

Kincardine
Cottage Rental close to lake Huron beach!

In-Town Cottage Near the Beach!

Kincardine
In-Town Cottage Near the Beach!
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

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, 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 Lake Rosalind. Bruce County Public Library - Cargill Branch and Pearl Lake 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.