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

Chepstow Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Chepstow holiday rentals

A covered outdoor seating area with a pergola, wooden benches, and a table with a bottle and glasses.

1. Ferryman's Lodge

Ferryman's Lodge
2.0 star property
Chepstow
The price is HK$2,961
HK$3,554 total
includes taxes & fees
8 Oct - 9 Oct
Ferryman's Lodge
A living room with two green sofas, a wooden coffee table, and a TV on a stand.

2. The Elements Residence

The Elements Residence
Chepstow
The price is HK$8,313
HK$8,905 total
includes taxes & fees
25 Oct - 26 Oct
The Elements Residence
A hot tub in an outdoor wooden enclosure with a tiled floor and a wicker chair nearby.

3. The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is HK$4,098
HK$4,918 total
includes taxes & fees
17 Oct - 18 Oct
The Honey Pot
A modern kitchen with white cabinets, a stainless steel oven, a sink, and a yellow toaster.

4. The Snug

The Snug
3.0 star property
Caerwent
The price is HK$2,544
HK$3,052 total
includes taxes & fees
13 Oct - 14 Oct
The Snug
A hot tub with a wooden deck, outdoor seating, and a view of the countryside.

5. Top Lodge

Top Lodge
2.0 star property
Caerwent
The price is HK$3,551
HK$4,261 total
includes taxes & fees
2 Oct - 3 Oct
Top Lodge
A modern living room with a sofa, armchair, coffee table, and a painting of red buses.

6. Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is HK$3,551
HK$4,261 total
includes taxes & fees
11 Oct - 12 Oct
Bottom Lodge
A stone wall entrance to a building with a black door and a small trash bin.

7. 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 HK$941
HK$941 total
includes taxes & fees
4 Oct - 5 Oct
Beautiful 1-bed Cottage in Trellech

8. A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.

A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.
Alvington
10.0 out of 10, Exceptional, (19 reviews)
"Very enjoyable stay would try to re-book when next in the area"
United States
Philip R.
The price is HK$1,029
HK$1,455 total
includes taxes & fees
1 Oct - 2 Oct
A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.
A wooden, arched, single-room cabin with two beds and two chairs, surrounded by grass and trees.

9. Broadstone Park Camping & Fishery

Broadstone Park Camping & Fishery
1.0 star property
Coleford
9.8 out of 10, Exceptional, (26 reviews)
"Brilliant holiday camp, very friendly staff, beautiful location, idea for familys ans couples."
United Kingdom
Tina
The price is HK$520
HK$623 total
includes taxes & fees
4 Oct - 5 Oct
Broadstone Park Camping & Fishery
A bedroom with a brick wall, a bed with white bedding, a wooden bench, a window with curtains, and a wardrobe.

10. One Bedroom Apartment Close to MOD

One Bedroom Apartment Close to MOD
Bristol
8.0 out of 10, Very good, (2 reviews)
"Everything in the property is well maintained ."
United Kingdom
Chijioke I.
One Bedroom Apartment Close to MOD
A hallway with a wooden staircase, a chandelier, and a radiator.

11. The Cranbrook - Stylish Bristol Stay - 10 Guests

The Cranbrook - Stylish Bristol Stay - 10 Guests
Bishopston
The price is HK$623
HK$1,663 total
includes taxes & fees
29 Sept - 30 Sept
The Cranbrook - Stylish Bristol Stay - 10 Guests
A narrow stone corridor with a small table and chairs, a door, and a window with a view into a room.

12. The Priory Cellars Abbots Leigh

The Priory Cellars Abbots Leigh
3.5 star property
Bristol
9.4 out of 10, Exceptional, (142 reviews)
"Nice place to stay for a few nights and very well equipped"
United Kingdom
John
The price is HK$790
HK$790 total
includes taxes & fees
30 Sept - 1 Oct
The Priory Cellars Abbots Leigh
A spacious lobby with a large sofa, patterned chairs, a wooden coffee table, and a large window offering a view of the street.

13. Orchard by UTDM

Orchard by UTDM
3.0 star property
Windmill Hill
The price is HK$589
HK$1,953 total
includes taxes & fees
29 Sept - 30 Sept
Orchard by UTDM
A conservatory with stone arches, potted plants, and a bench.

14. The Orangery Apartment

The Orangery Apartment
4.0 star property
Bristol
9.6 out of 10, Exceptional, (81 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 HK$831
HK$831 total
includes taxes & fees
1 Oct - 2 Oct
The Orangery Apartment
A bedroom with a wooden headboard, a bed with a gray blanket, a pillow with a floral design, and a cat on the bed.

15. 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 HK$890
HK$1,517 total
includes taxes & fees
4 Oct - 5 Oct
Higgihaus 26 Clare Street Aparthotel
A spacious loft-style living area with a large wooden dining table, multiple seating options, and a large sliding glass door leading to a balcony.

16. Bilsham Meadows

Bilsham Meadows
3.0 star property
Bristol
The price is HK$12,568
HK$15,082 total
includes taxes & fees
1 Oct - 2 Oct
Bilsham Meadows
A traditional building with a sign reading "Welcome to The Olde Bull Inn" at night.

17. Lovely 1-bed Loft in Newport

Lovely 1-bed Loft in Newport
3.0 star property
Caerleon
8.6 out of 10, Excellent, (7 reviews)
"Location very good for Caerleon. Clean and spacious "
United Kingdom
JAYNE
The price is HK$731
HK$877 total
includes taxes & fees
30 Sept - 1 Oct
Lovely 1-bed Loft in Newport
A modern kitchen with a stainless steel sink, a round mirror, and a potted plant.

18. 526 Gloucester Flat 1 - Hopewell

526 Gloucester Flat 1 - Hopewell
Horfield
9.6 out of 10, Exceptional, (4 reviews)
"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 HK$800
HK$1,216 total
includes taxes & fees
11 Oct - 12 Oct
526 Gloucester Flat 1 - Hopewell
A modern kitchen with wooden cabinets, a dining table with chairs, and large windows with curtains.

19. 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, (217 reviews)
"Great location next to the shops and 1 min to some restaurants, or ten mins walk to the bars and restaurants by the river. Apartment was amazing. Two bedrooms, two bathrooms. Kitchen with microwave. Clean and very spacious."
United Kingdom
GILLIAN
The price is HK$771
HK$925 total
includes taxes & fees
4 Oct - 5 Oct
PREMIER SUITES PLUS Bristol Cabot Circus
A marina at dusk with boats docked, buildings in the background, and a calm water surface reflecting the lights.

20. Stylish Marina Apartment with Stunning Views

Stylish Marina Apartment with Stunning Views
Portishead
9.6 out of 10, Exceptional, (4 reviews)
"We had a lovely stay in this flat, which had a comfortable bed, a good shower, a well provisioned kitchen and a nice view of the marina."
United States
Ruth S.
The price is HK$842
HK$1,320 total
includes taxes & fees
30 Sept - 1 Oct
Stylish Marina Apartment with Stunning Views
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

Celtic Manor Resort

Celtic Manor Resort

10/10 Excellent
"The hotel itself is magnificent, sitting on the hillside overlooking the Welsh and English border. From the moment you step in you know you are inside a great hotel and full of history. The team where attentive and ensured we were looked after at check in and throughout. The upgrade was reasonably priced and well worth it having full access to the Signature areas. The signature lounge was impressive and with stunning views. Thank you all for a very enjoyable stay."
Kiran 1-night trip
Posted 1 hour ago
Celtic Manor Resort

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:

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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.

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 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.