Holiday Rentals in Chepstow

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Our top choices for Chepstow holiday rentals

Cottage in Caerwent

Top Lodge
2.0 star property
The price is €459
includes taxes & fees
28 Dec - 29 Dec
Top Lodge

Cottage in Chepstow

The Honey Pot
3.5 star property
The price is €527
includes taxes & fees
4 Jan - 5 Jan 2026
The Honey Pot

Cottage in Trellech United

The Comfy Cow
3.5 star property
The price is €448
includes taxes & fees
29 Dec - 30 Dec
The Comfy Cow

Cottage in Caerwent

The Snug
3.0 star property
The price is €337
includes taxes & fees
5 Jan - 6 Jan 2026
The Snug

Cottage in Caerwent

Bottom Lodge
3.0 star property
The price is €459
includes taxes & fees
29 Dec - 30 Dec
Bottom Lodge
1.0 star property
9.8 out of 10, Exceptional, (23)
"Amazing place for work or holiday. Clean affordable and great staff"
United Kingdom
Luke
The price is €69
includes taxes & fees
30 Dec - 31 Dec
Broadstone Park Camping & Fishery

Apartment in Clifton

Frederick Place Your Apartment
4.5 star property
7.6 out of 10, Good, (7)
"The apartment is very nice (if a little run-down and stained) and well-located for the university. There is a lot of space, and the beds are very comfortable, although it is quite hot and there was only one fan. However, all of that was overshadowed by the fact that one bedroom was crawling with bedbugs. It completely ruined our stay, and our trip to Bristol, which we had to cut short, and created a massive headache for us logistically, as well as a lot of anxiety. The managers didn't...
United Kingdom
Hanna
Frederick Place Your Apartment

Apartment in Clifton

Redmayne House
3.5 star property
9.4 out of 10, Exceptional, (28)
"Fantastic property could not fault it will definitely stay again "
United Kingdom
Debra
The price is €113
includes taxes & fees
4 Jan - 5 Jan 2026
Redmayne House
3.5 star property
9.0 out of 10, Wonderful, (41)
"Really lovely accommodation. Staff were very friendly and helpful and made sure check in and out was easy. We went to the pub for food and it was excellent - great menu and well cooked and presented. Staff were really helpful again Lovely area for a walk or trip to the vineyard "
United Kingdom
Helen
The price is €86
includes taxes & fees
18 Jan - 19 Jan 2026
The Coach House and The Stable

Apartment in Bristol

Your Apartment Clifton House
3.0 star property
7.6 out of 10, Good, (93)
"Fantastic stay at a fantastic apartment! Would highly recommend."
United Kingdom
Montague Joshua Paul
Your Apartment Clifton House

Apartment in Bristol

Beech House
4.0 star property
9.4 out of 10, Exceptional, (183)
"this has to be one of the best equipped rooms ive stayed in value for money was excellent "
United Kingdom
Jane
The price is €104
includes taxes & fees
18 Jan - 19 Jan 2026
Beech House

Apartment in Bristol

Arabica House - YourApartment
3.5 star property
9.4 out of 10, Exceptional, (51)
"great property for easy access to Bristol city centre and the waterfront"
United Kingdom
debbie
The price is €140
includes taxes & fees
26 Dec - 27 Dec
Arabica House - YourApartment
9.4 out of 10, Exceptional, (3)
"I loved the independence of the flat. The kitchen was fab but could have done with a microwave or even an oven dish. I did not like seeing all the bins at the front full to the brim. Loved the shower and the bed was okay but badly needed a bedside light. A small chest of drawers would also of been handy. I would book again. "
United Kingdom
Vanessa
The price is €105
includes taxes & fees
28 Dec - 29 Dec
526 Gloucester Flat 1 - Hopewell
3.5 star property
9.4 out of 10, Exceptional, (128)
"Awesome hosts and great accommodations!"
United States
Susan
The price is €109
includes taxes & fees
1 Jan - 2 Jan 2026
The Priory Cellars Abbots Leigh

Apartment in Stroud

Old Fleece Apartments
3.5 star property
8.6 out of 10, Excellent, (39)
"Far better than expected for the price will use again"
United Kingdom
brian
The price is €90
includes taxes & fees
11 Jan - 12 Jan 2026
Old Fleece Apartments

Cottage in Llanishen

De Courceys Manor Cottages
3.5 star property
9.2 out of 10, Wonderful, (33)
"Quiet and very clean. Shame you aren’t allowed to use any facilities or gardens, very misleading as they are all shown in the photos when booking "
United Kingdom
Lee
The price is €115
includes taxes & fees
6 Jan - 7 Jan 2026
De Courceys Manor Cottages

Aparthotel in Bristol City Centre

PREMIER SUITES PLUS Bristol Cabot Circus
4.0 star property
8.6 out of 10, Excellent, (194)
"Great place to stay with all the conveniences needed for a family of 4."
Canada
Macie
The price is €96
includes taxes & fees
30 Dec - 31 Dec
PREMIER SUITES PLUS Bristol Cabot Circus

Apartment in Bristol

The Orangery Apartment
4.0 star property
9.6 out of 10, Exceptional, (67)
"Its a good, lovely and quiet location."
United Kingdom
Adeola
The price is €103
includes taxes & fees
12 Jan - 13 Jan 2026
The Orangery Apartment

Cottage in Trellech United

Beautiful 1-bed Cottage in Trellech
3.0 star property
9.0 out of 10, Wonderful, (22)
"A lovely private cottage next to a great pub. "
United States
David
The price is €92
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful 1-bed Cottage in Trellech
4.0 star property
7.4 out of 10, Good, (99)
"Great place, very central, we went to the balloon fiesta and it was I. The ideal location, about half hour walk away,the room was clean tidy and very comfortable "
United Kingdom
Joy
Your Apartment I Clifton Village
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, 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 €76 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 a holiday rental 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. Visitors like the top-notch restaurants and spas in Chepstow. Allow lots of time to check out the riverfront and bars during your visit.

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

Rural retreat, large house sleeps 17+ set in stunning countryside amazing views: This highly rated holiday home rental in Chepstow offers a patio, a garden and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, an oven and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Chepstow?

Choose from 7 Expedia holiday rentals in Chepstow for a memorable holiday.

What’s there to see and do in Chepstow?

Wye Valley and River Wye are a couple of scenic spots to enjoy the outdoors, whereas Chepstow Museum is one of the cultural attractions. Chepstow Racecourse and St. Pierre Country Club are other places to visit while you're in town.

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 feature extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for small groups.