Chepstow Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Chepstow

Cottage in Kincardine

9.8 out of 10, Exceptional, (11)
"Location, cottage cleanliness, and amenities were excellent! Our family enjoyed every moment in the cottage on Queen."
Canada
Peter M.
Fully Renovated Cottage on Queen, 3min walk from Beach and Downtown Adventures!

Holiday Home in Paisley

9.8 out of 10, Exceptional, (22)
"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."
Canada
Roberto
Secluded 3 bedroom bungalow on the Saugeen River with 85-acres.

Cottage in Inverhuron

10.0 out of 10, Exceptional, (5)
"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!"
Canada
Juli L.
Cedarhaven - 2 King beds! Hot Tub, Gas Fireplace

Cottage in Inverhuron

Newly Built 3 Bedroom Cottage, Steps to the Beach

Apartment in Kincardine

10.0 out of 10, Exceptional, (5)
"Apartment was bright and very clean and close to everything including the venues for the Scottish Festival. "
Canada
Mary Ellen H.
Historic 2 Bedroom Beach Lofts - Boutique Styled, Beach, Lake, stay Drifter Loft

Cottage in 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.

Cottage in Hanover

8.4 out of 10, Very good, (5)
"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. "
Canada
Jenny M.
Waterfront Bliss: Firepit & BBQ Cottage R

Apartment in Wingham

10.0 out of 10, Exceptional, (8)
"This property is clean, well appointed and quiet. A good home base for exploring the area. "
Canada
Theresa R.
Two bedroom river side apartment with large private yard

Apartment in Kincardine

10.0 out of 10, Exceptional, (13)
"Another amazing stay! Cleanliness, quality, design, location all make it the best rental in the area. "
Canada
Anna
Historic 1 Bedroom Beach Loft - Boutique Styled, Beach, Lake, stay Drifter Lofts

Cottage in 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

Cottage in Kincardine

10.0 out of 10, Exceptional, (2)
"Beautiful sunsets"
United States
rose h.
Modern Classic *LakeViews*

Holiday Home in Wingham

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

Cottage in 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

Holiday Home in Kincardine

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

Cottage in 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!

Holiday Home in Walkerton

Walkerton Sauna Suite

Holiday Home in Kincardine

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

Holiday Home in Kincardine

Cottage Rental close to lake Huron beach!

Holiday Home in Kincardine

The GOAT Lakehouse

Holiday Home in 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.

Black Friday Sale

Save up to 40% on select hotels
Save an average of 15% on thousands of hotels when you're signed in

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 favourite 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 depend 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 might find you 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 Pearl Lake. Walkerton Golf & Curling Club and Black Horse Golf 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.