The ruins of a large, historic stone building with multiple arches and a tall, narrow tower.

Holiday Rentals in Chepstow

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Our top choices for Chepstow holiday rentals

1. The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is €595
includes taxes & fees
13 Nov - 14 Nov
The Honey Pot

2. Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is €540
includes taxes & fees
13 Nov - 14 Nov
Bottom Lodge

3. The Snug

The Snug
3.0 star property
Caerwent
The price is €387
includes taxes & fees
19 Nov - 20 Nov
The Snug

4. Top Lodge

Top Lodge
3.0 star property
Caerwent
The price is €540
includes taxes & fees
12 Nov - 13 Nov
Top Lodge

5. Bilsham Meadows

Bilsham Meadows
3.0 star property
Bristol
The price is €1,910
includes taxes & fees
30 Nov - 1 Dec
Bilsham Meadows

6. Livin' Serviced Apartments - Newport

Livin' Serviced Apartments - Newport
2.0 star property
St Julians
10.0 out of 10, Exceptional, (3 reviews)
"Great apartment. Very spacious. Absolutely loved staying here. Will definitely do it again"
United Kingdom
Lucy
The price is €61
includes taxes & fees
9 Nov - 10 Nov
Livin' Serviced Apartments - Newport

7. PREMIER SUITES Bristol Redcliffe

PREMIER SUITES Bristol Redcliffe
4.0 star property
Bristol Floating Harbour
8.6 out of 10, Excellent, (194 reviews)
"Great flat Stayed for o e night so only used for the night Well equipped"
United Kingdom
rasiah
The price is €107
includes taxes & fees
12 Nov - 13 Nov
PREMIER SUITES Bristol Redcliffe

8. Beautiful 1-bed Cottage in Trellech

Beautiful 1-bed Cottage in Trellech
3.0 star property
Trellech United
9.2 out of 10, Wonderful, (25 reviews)
"Lovely staff and great space to relax."
United Kingdom
Eva
The price is €108
includes taxes & fees
22 Nov - 23 Nov
Beautiful 1-bed Cottage in Trellech

9. Frederick Place Your Apartment

Frederick Place Your Apartment
4.5 star property
Clifton
7.4 out of 10, Good, (12 reviews)
"Beautiful, spacious apartment in a fantastic location, cant recommend enough"
United Kingdom
Roger
The price is €203
includes taxes & fees
20 Nov - 21 Nov
Frederick Place Your Apartment

10. Quay Apartments Clarence House

Quay Apartments Clarence House
3.5 star property
St Julians
8.6 out of 10, Excellent, (162 reviews)
"Convenient location close to train station, safe area, clean and has all the amenities needed. Will stay again"
United Kingdom
KONSTANTINOS
The price is €83
includes taxes & fees
29 Nov - 30 Nov
Quay Apartments Clarence House

11. Your Apartment I Clifton Village

Your Apartment I Clifton Village
4.0 star property
Clifton
7.4 out of 10, Good, (113 reviews)
"A great location in central Clifton, had everything we needed and easily accesible"
United Kingdom
Erin
The price is €145
includes taxes & fees
20 Nov - 21 Nov
Your Apartment I Clifton Village

12. The Orangery Apartment

The Orangery Apartment
4.0 star property
Bristol
9.6 out of 10, Exceptional, (85 reviews)
"The apartment was so roomy . Space to park and a great little pub at the end of the road . Nick was an excellent host !"
Australia
Narelle
The price is €96
includes taxes & fees
9 Nov - 10 Nov
The Orangery Apartment

13. Higgihaus 26 Clare Street Aparthotel

Higgihaus 26 Clare Street Aparthotel
3.5 star property
Bristol City Centre
8.0 out of 10, Very good, (5 reviews)
"Great little apartment which is well located for the centre of Bristol and the docks and near plenty of pubs and restaurants. We used it as a base for some historical touristy walks in the area, everything is within walking distance"
United Kingdom
Amanda
The price is €173
includes taxes & fees
16 Nov - 17 Nov
Higgihaus 26 Clare Street Aparthotel

14. Your Apartment Clifton House

Your Apartment Clifton House
3.0 star property
Bristol
7.4 out of 10, Good, (118 reviews)
"Excellent room and great location Online check I wasn't the easiest but no issues once I arrived. Really nice property for the price"
United Kingdom
Freddie
The price is €139
includes taxes & fees
12 Nov - 13 Nov
Your Apartment Clifton House

15. Hidden Well

Hidden Well
2.0 star property
Bristol
The price is €1,739
includes taxes & fees
11 Nov - 12 Nov
Hidden Well

16. The Priory Cellars Abbots Leigh

The Priory Cellars Abbots Leigh
3.5 star property
Bristol
9.4 out of 10, Exceptional, (144 reviews)
"Nice place to stay for a few nights and very well equipped"
United Kingdom
John
The price is €91
includes taxes & fees
15 Nov - 16 Nov
The Priory Cellars Abbots Leigh

17. PREMIER SUITES PLUS Bristol Cabot Circus

PREMIER SUITES PLUS Bristol Cabot Circus
4.0 star property
Bristol City Centre
8.6 out of 10, Excellent, (222 reviews)
"Excellent….. Will definitely stay again on my next overnight stay A******"
United Kingdom
Allie
The price is €107
includes taxes & fees
15 Nov - 16 Nov
PREMIER SUITES PLUS Bristol Cabot Circus

18. Hotwells Your Apartment

Hotwells Your Apartment
3.0 star property
Clifton
7.4 out of 10, Good, (11 reviews)
"Small clean room cosy and warm bus stop right outside the apartments but very noisy you can hear every move of other residents in the property"
Ireland
Hoa Minh
The price is €126
includes taxes & fees
12 Nov - 13 Nov
Hotwells Your Apartment

19. Your Apartment - Pembroke House

Your Apartment - Pembroke House
4.0 star property
Clifton
8.8 out of 10, Excellent, (10 reviews)
"Beautiful property in beautiful Clifton. Will definitely book again if i'm ever in Bristol!"
Netherlands
reihana
The price is €149
includes taxes & fees
11 Nov - 12 Nov
Your Apartment - Pembroke House

20. Colston Street - Your Apartment

Colston Street - Your Apartment
3.0 star property
Bristol
8.4 out of 10, Very good, (10 reviews)
"I enjoyed it highly recommended.....will do it anytime again.....perfect for a get away peace quiet an great....."
United Kingdom
Sansha
The price is €145
includes taxes & fees
13 Nov - 14 Nov
Colston Street - Your Apartment
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 €83 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. 

Explore a world of travel with Expedia

Frequently asked questions

Can I find a holiday rental in Chepstow?

Yes, there are holiday rentals in Chepstow close to Chepstow Leisure Centre, 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?

6 Bed House Sleeps 13 - Private Garden: This holiday home rental outside of Chepstow is equipped with a garden, laundry facilities and free WiFi to help you feel comfortable during your stay. It has 6 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Chepstow?

Choose from 14 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.