Search Holiday Rentals in Chepstow

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Top Holiday Rentals in Chepstow

One-of-a-kind cottage steps from Lake Huron!
10.0 out of 10, Exceptional, (1)
"Close to our favourite places, tons of parks, beaches, foxes, you name it they got it. Peaceful and beautiful neighbourhood. Would come again in a heartbeat."
One-of-a-kind cottage steps from Lake Huron!
Stoney Island Sunsets. Blue Nugget is located on the sandy shores of Lake Huron.
Stoney Island Sunsets. Blue Nugget is located on the sandy shores of Lake Huron.
Rustic Rural Retreat
The price is £237
includes taxes & fees
1 Jul - 2 Jul
Rustic Rural Retreat
Save an average of 15% on thousands of hotels when you're signed in
Newly Built 3 Bedroom Cottage, Steps to the Beach
Newly Built 3 Bedroom Cottage, Steps to the Beach
Great Lake Cabin Retreat
The price is £69
includes taxes & fees
19 Jun - 20 Jun
Great Lake Cabin Retreat
Secluded 3 bedroom bungalow on the Saugeen River with 85-acres.
10.0 out of 10, Exceptional, (12)
"This cabin felt like home the moment we stepped in. The personal stories and touches make things feel that much more welcoming. The book collection and dvd collection is amazing. There are fun games, things to do, entertainment inside and out. The property is nothing short of stunning. The sunrise, the wildlife, the river and views all around. The trail system is so well laid out. So much to explore. Mark is fantastic and readily available with any questions or suggestions. We would highly...
Secluded 3 bedroom bungalow on the Saugeen River with 85-acres.
Kincardine House
9.8 out of 10, Exceptional, (9)
"Beautiful heritage property, obviously lovingly restored. The location is amazing, walking distance to all amenities."
Kincardine House
Waterfront Bliss: Firepit & BBQ Cottage Retreat
10.0 out of 10, Exceptional, (1)
"We were thankful to find a beautiful cottage on the water without the need of driving hours up north. Great layout and amenities, town is very close by and easy to get to. Neighbourhood is very nice would definitely visit again and recommend"
Waterfront Bliss: Firepit & BBQ Cottage Retreat
Fully Renovated Cottage on Queen, 3min walk from Beach and Downtown Adventures!
Fully Renovated Cottage on Queen, 3min walk from Beach and Downtown Adventures!
PIER280-Lakefront Beauty, Lake access
10.0 out of 10, Exceptional, (5)
PIER280-Lakefront Beauty, Lake access
Historic 1 Bedroom Beach Loft - Boutique Styled, Beach, Lake, stay Drifter Lofts
10.0 out of 10, Exceptional, (9)
"Amazing, well appointed comfortable loft in excellent location close to the best restaurants, the beach, trails etc. The loft had everything one would need, and is beautifully decorated with many unique Canadian touches. All furnishings are extremely comfy, especially the super comfortable bed! Enjoyable week all around. Thanks to our hosts who are wonderful."
Historic 1 Bedroom Beach Loft - Boutique Styled, Beach, Lake, stay Drifter Lofts
escape, relax in modern convenience & comfort.
10.0 out of 10, Exceptional, (2)
"The house is a great open space with a huge yard to relax in. It is in a very quiet area and a great spot to get away."
escape, relax in modern convenience & comfort.
Historic 2 Bedroom Beach Lofts - Boutique Styled, Beach, Lake, stay Drifter Loft
10.0 out of 10, Exceptional, (1)
"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, (4)
"Really enjoyed our stay, the hosts where very accomidating. No issues to speak of whatsoever would most certainly stay there again and will next year!"
Two bedroom river side apartment with large private yard
Relaxing retreat with active options: Modern Bungalow near trails and park
10.0 out of 10, Exceptional, (2)
"Great place!"
Relaxing retreat with active options: Modern Bungalow near trails and park
Family Fun
10.0 out of 10, Exceptional, (12)
"The home and neighborhood were lovely. The home was clean and well appointed. We really enjoyed our stay."
Family Fun
Peabody Log Cabin - Three Bedroom Cottage, Sleeps 8
Peabody Log Cabin - Three Bedroom Cottage, Sleeps 8
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!
In-Town Cottage Near the Beach!
In-Town Cottage Near the Beach!
"stunning Serenity Cove On The Lake Cozy Cottage"
2.0 star property
"stunning Serenity Cove On The Lake Cozy Cottage"
Don't see what you're looking for?
See all available properties in Chepstow
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.

Other types of properties in Chepstow you may be interested in

The Chepstow Inn
3.5 star property
9.8 out of 10, Exceptional, (77)
"Great hospitality from Kym. Breakfasts were a real treat. Great location to visit small town Ontario ."
The price is £162
includes taxes & fees
20 Jun - 21 Jun
The Chepstow Inn
SureStay Plus Hotel by Best Western Kincardine
2.5 star property
8.2 out of 10, Very good, (681)
"We will definitely be returning!"
The price is £87
includes taxes & fees
25 Jun - 26 Jun
SureStay Plus Hotel by Best Western Kincardine
Comfort Inn & Suites
2.5 star property
8.2 out of 10, Very good, (80)
"The grass was very long. I feel it could have looked nicer had the lawns been maintained."
The price is £110
includes taxes & fees
27 Jun - 28 Jun
Comfort Inn & Suites
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.

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 £69 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?

Rustic Rural Retreat: This holiday home rental outside of Chepstow has laundry facilities and WiFi to help you feel perfectly comfortable in your new surroundings.

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 Brant Tract Trails Trailhead. Walkerton Golf & Curling Club and Playtime Casino Hanover 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.

Recent reviews of Chepstow properties
Expedia verified reviews