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

Chepstow Vacation Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Chepstow vacation rentals

Cottage | Property grounds

1. Ferryman's Lodge

Ferryman's Lodge
2.0 star property
Chepstow
The price is AED 1,402
AED 1,683 total
includes taxes & fees
24 Sep - 25 Sep
Ferryman's Lodge
Smart TV

2. The Elements Residence

The Elements Residence
Chepstow
The price is AED 3,936
AED 4,497 total
includes taxes & fees
27 Sep - 28 Sep
The Elements Residence
Cottage | Interior

3. The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is AED 1,940
AED 2,328 total
includes taxes & fees
26 Sep - 27 Sep
The Honey Pot
Fridge, electric kettle, toaster, cookware/dishes/utensils

4. The Snug

The Snug
3.0 star property
Caerwent
The price is AED 1,204
AED 1,445 total
includes taxes & fees
28 Sep - 29 Sep
The Snug
Cottage | Living area | Fireplace

5. Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is AED 1,681
AED 2,017 total
includes taxes & fees
9 Oct - 10 Oct
Bottom Lodge
Outdoor dining

6. Top Lodge

Top Lodge
2.0 star property
Caerwent
The price is AED 1,681
AED 2,017 total
includes taxes & fees
2 Oct - 3 Oct
Top Lodge
Cabin, Shared Bathroom (camping pod)

7. 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 AED 236
AED 283 total
includes taxes & fees
21 Oct - 22 Oct
Broadstone Park Camping & Fishery
Cottage | Property entrance

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 AED 414
AED 414 total
includes taxes & fees
4 Oct - 5 Oct
Beautiful 1-bed Cottage in Trellech
Interior

9. 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 AED 487
AED 699 total
includes taxes & fees
22 Sep - 23 Sep
A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.
Property grounds

10. The Priory Cellars Abbots Leigh

The Priory Cellars Abbots Leigh
3.5 star property
Bristol
9.4 out of 10, Exceptional, (141 reviews)
"Nice place to stay for a few nights and very well equipped"
United Kingdom
John
The price is AED 374
AED 374 total
includes taxes & fees
21 Sep - 22 Sep
The Priory Cellars Abbots Leigh
Cottage | Dining

11. Bilsham Meadows

Bilsham Meadows
3.0 star property
Bristol
The price is AED 5,951
AED 7,141 total
includes taxes & fees
28 Sep - 29 Sep
Bilsham Meadows
Terrace/patio

12. The Orangery Apartment

The Orangery Apartment
4.0 star property
Bristol
9.6 out of 10, Exceptional, (80 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 AED 394
AED 394 total
includes taxes & fees
22 Sep - 23 Sep
The Orangery Apartment
Interior

13. The Cranbrook - Stylish Bristol Stay - 10 Guests

The Cranbrook - Stylish Bristol Stay - 10 Guests
Bishopston
The price is AED 320
AED 812 total
includes taxes & fees
28 Sep - 29 Sep
The Cranbrook - Stylish Bristol Stay - 10 Guests
Fridge, microwave, oven, stovetop

14. 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 AED 438
AED 635 total
includes taxes & fees
20 Oct - 21 Oct
526 Gloucester Flat 1 - Hopewell
Higgihaus Apartment 2, Clare St Aparthotel | 1 bedroom, laptop workspace, iron/ironing board, WiFi (free)

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 AED 440
AED 740 total
includes taxes & fees
18 Oct - 19 Oct
Higgihaus 26 Clare Street Aparthotel
Property grounds

16. HartHill Grange Bunkhouse - Unique 1850's Rural Country Accommodation

HartHill Grange Bunkhouse - Unique 1850's Rural Country Accommodation
Lydney
10.0 out of 10, Exceptional, (30 reviews)
"A great property with a few clearly defined spaces to enjoy. The location was great for an enjoyable pleasant weekend, and the process with the host was very efficient and slick."
United Kingdom
Samuel P.
The price is AED 3,690
AED 4,211 total
includes taxes & fees
21 Sep - 22 Sep
HartHill Grange Bunkhouse - Unique 1850's Rural Country Accommodation
Outdoor dining

17. Sunnyside Cottage - Rural 2-bedroom apartment

Sunnyside Cottage - Rural 2-bedroom apartment
Bristol
10.0 out of 10, Exceptional, (7 reviews)
"Lovely little place perfectly positioned for exploring Bristol.and the coast of the Avon."
United Kingdom
Kieran J.
The price is AED 567
AED 650 total
includes taxes & fees
27 Sep - 28 Sep
Sunnyside Cottage - Rural 2-bedroom apartment
Studio | Exterior

18. Lovely 1-bed Loft in Newport

Lovely 1-bed Loft in Newport
3.0 star property
Caerleon
8.4 out of 10, Very good, (6 reviews)
"Location very good for Caerleon. Clean and spacious "
United Kingdom
JAYNE
The price is AED 346
AED 415 total
includes taxes & fees
23 Sep - 24 Sep
Lovely 1-bed Loft in Newport
TV

19. PREMIER SUITES Bristol Redcliffe

PREMIER SUITES Bristol Redcliffe
4.0 star property
Bristol Floating Harbour
8.6 out of 10, Excellent, (191 reviews)
"Great flat Stayed for o e night so only used for the night Well equipped"
United Kingdom
rasiah
The price is AED 365
AED 438 total
includes taxes & fees
27 Sep - 28 Sep
PREMIER SUITES Bristol Redcliffe
Lounge

20. Orchard by UTDM

Orchard by UTDM
3.0 star property
Windmill Hill
The price is AED 279
AED 925 total
includes taxes & fees
29 Sep - 30 Sep
Orchard by UTDM
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

The Coach & Horses Hotel

The Coach & Horses Hotel

10/10 Excellent
"Fantastic clean tidy and well managed"
Michael 1-night trip
Posted less than an hour ago
The Coach & Horses Hotel

Frequently asked questions

Can I find a vacation rental in Chepstow?

Yes, there are vacation rentals in Chepstow close to Chepstow Leisure Centre, or you can choose a secluded option if you'd like a relaxing place to 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 vacation home rentals in Chepstow?

6 Bed House Sleeps 13 - Private Garden: This vacation home rental near 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 you can cook with friends or family.

How many vacation rentals are there in Chepstow?

Choose from 13 Expedia vacation rentals in Chepstow for a memorable vacation.

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 vacation rental in Chepstow like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Chepstow. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for families.