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

Search Holiday Rentals in Chepstow

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Chepstow holiday rentals

Cottage | Interior

1. The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is ฿17,651
฿21,181 total
includes taxes & fees
17 Sept - 18 Sept
The Honey Pot
Cottage

2. Ferryman's Lodge

Ferryman's Lodge
2.0 star property
Chepstow
The price is ฿12,755
฿15,306 total
includes taxes & fees
24 Sept - 25 Sept
Ferryman's Lodge
Private kitchen

3. The Snug

The Snug
3.0 star property
Caerwent
The price is ฿10,956
฿13,147 total
includes taxes & fees
10 Sept - 11 Sept
The Snug
Cottage | Living area

4. Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is ฿15,292
฿18,351 total
includes taxes & fees
9 Sept - 10 Sept
Bottom Lodge
Outdoor dining

5. Top Lodge

Top Lodge
2.0 star property
Caerwent
The price is ฿15,292
฿18,351 total
includes taxes & fees
14 Sept - 15 Sept
Top Lodge
Cottage | Property entrance

6. 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 ฿4,528
฿4,528 total
includes taxes & fees
8 Sept - 9 Sept
Beautiful 1-bed Cottage in Trellech
Property grounds

7. The Priory Cellars Abbots Leigh

The Priory Cellars Abbots Leigh
3.5 star property
Bristol
9.4 out of 10, Exceptional, (138 reviews)
"Lovely host, great location and a unique spacious accommodation with a few thoughtful extras."
United Kingdom
Le-Anne
The price is ฿3,401
฿3,401 total
includes taxes & fees
6 Sept - 7 Sept
The Priory Cellars Abbots Leigh
Cabin, Shared Bathroom (camping pod)

8. Broadstone Park Camping & Fishery

Broadstone Park Camping & Fishery
1.0 star property
Coleford
9.8 out of 10, Exceptional, (26 reviews)
"Lovely little pod. Great showers."
United Kingdom
Michelle
The price is ฿2,238
฿2,685 total
includes taxes & fees
8 Sept - 9 Sept
Broadstone Park Camping & Fishery
Cottage | Dining

9. Bilsham Meadows

Bilsham Meadows
3.0 star property
Bristol
The price is ฿54,131
฿64,958 total
includes taxes & fees
10 Sept - 11 Sept
Bilsham Meadows
Terrace/patio

10. The Orangery Apartment

The Orangery Apartment
4.0 star property
Bristol
9.6 out of 10, Exceptional, (79 reviews)
"Lovely clean, spacious, well-equipped apartment in a beautiful building. The accommodation has everything you need for a short or long stay. Hosts were very welcoming and helpful. There are lovely walks in the surrounding area and it is also very convenient for getting into Bristol."
United States
Patricia
The price is ฿3,580
฿3,580 total
includes taxes & fees
20 Sept - 21 Sept
The Orangery Apartment
Studio | Exterior

11. Lovely 1-bed Loft in Newport

Lovely 1-bed Loft in Newport
3.0 star property
Caerleon
8.8 out of 10, Excellent, (5 reviews)
"Location very good for Caerleon. Clean and spacious "
United Kingdom
JAYNE
The price is ฿3,148
฿3,777 total
includes taxes & fees
6 Sept - 7 Sept
Lovely 1-bed Loft in Newport
Living area

12. Your Stay Bristol Orchard Gate

Your Stay Bristol Orchard Gate
3.5 star property
Bristol
8.8 out of 10, Excellent, (45 reviews)
"This apartment was clean, warm and had everything we needed. "
United Kingdom
claire
Your Stay Bristol Orchard Gate
Premium Apartment, 2 Bedrooms | Living area

13. Quay Apartments Clarence House

Quay Apartments Clarence House
3.5 star property
St Julians
8.4 out of 10, Very good, (157 reviews)
"Fast and easy check-in, helpful staff and quick production of a VAT invoice for expenses. The apartment was clean, roomy and comfortable, with a good bed, large TV, well equipped kitchen and great shower too. Parking is very convenient and placed at the back of the building in the multi-storey car park. Local supermarket very close too. Great."
United Kingdom
Andrew
The price is ฿2,551
฿3,061 total
includes taxes & fees
6 Sept - 7 Sept
Quay Apartments Clarence House
Higgihaus Apartment 2, Clare St Aparthotel

14. 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)
"Lovwly property rught in the thick of it!"
United Kingdom
Tracey
The price is ฿4,028
฿6,767 total
includes taxes & fees
7 Sept - 8 Sept
Higgihaus 26 Clare Street Aparthotel
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chepstow Hotel Reviews

The Manor House At Celtic Manor

The Manor House At Celtic Manor

10/10 Excellent
"Very friendly staff. Great food. Lovely Room."
Simon 1-night trip
Posted 1 hour ago
The Manor House At Celtic Manor

Find out more about Chepstow

Search for holiday rentals in Chepstow on Expedia! You can easily find your home rentals, villas, holiday apartments in Chepstow using one of the methods below:

  • View our selection of featured holiday rentals in Chepstow
  • Use the map to find apartments and other holiday homes in the Chepstow neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chepstow while they last

Look no further and take a look at our great range of rental properties in Chepstow!

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.

How many holiday rentals are there in Chepstow?

Choose from 13 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.