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
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Chepstow holiday rentals

A stone wall, a patterned metal fence, and a building with a tiled roof.

1. Ferryman's Lodge

Ferryman's Lodge
2.0 star property
Chepstow
The price is S$586
includes taxes & fees
24 Sept - 25 Sept
Ferryman's Lodge
A hot tub in an outdoor wooden enclosure with a tiled floor and a wicker chair nearby.

2. The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is S$811
includes taxes & fees
17 Sept - 18 Sept
The Honey Pot
A modern kitchen with white cabinets, a stainless steel oven, a sink, and a yellow toaster.

3. The Snug

The Snug
3.0 star property
Caerwent
The price is S$503
includes taxes & fees
17 Sept - 18 Sept
The Snug
A modern living room with a sofa, armchair, coffee table, and a painting of red buses.

4. Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is S$703
includes taxes & fees
19 Sept - 20 Sept
Bottom Lodge
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 S$703
includes taxes & fees
2 Oct - 3 Oct
Top Lodge
A stone wall entrance to a building with a black door and a small trash bin.

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 S$155
includes taxes & fees
4 Oct - 5 Oct
Beautiful 1-bed Cottage in Trellech
A wooden, arched, single-room cabin with two beds and two chairs, surrounded by grass and trees.

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 S$101
includes taxes & fees
25 Sept - 26 Sept
Broadstone Park Camping & Fishery
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.

8. Bilsham Meadows

Bilsham Meadows
3.0 star property
Bristol
The price is S$2,487
includes taxes & fees
14 Oct - 15 Oct
Bilsham Meadows
A narrow stone corridor with a small table and chairs, a door, and a window with a view into a room.

9. The Priory Cellars Abbots Leigh

The Priory Cellars Abbots Leigh
3.5 star property
Bristol
9.4 out of 10, Exceptional, (139 reviews)
"Lovely host, great location and a unique spacious accommodation with a few thoughtful extras."
United Kingdom
Le-Anne
The price is S$130
includes taxes & fees
20 Sept - 21 Sept
The Priory Cellars Abbots Leigh
A conservatory with stone arches, potted plants, and a bench.

10. 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 S$137
includes taxes & fees
20 Sept - 21 Sept
The Orangery Apartment
A living room with a black sofa, a glass coffee table, and a fireplace.

11. 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
The price is S$293
includes taxes & fees
15 Sept - 16 Sept
Your Stay Bristol Orchard Gate
A traditional building with a sign reading "Welcome to The Olde Bull Inn" at night.

12. 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 S$145
includes taxes & fees
14 Sept - 15 Sept
Lovely 1-bed Loft in Newport
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 S$360
includes taxes & fees
15 Sept - 16 Sept
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

Ramada by Wyndham Bristol West

Ramada by Wyndham Bristol West

10/10 Excellent
"Clean and good place to stay in. Even the nightly price is fair. Strongly recommended"
NACER 1-night trip
Posted less than an hour ago
Ramada by Wyndham Bristol West

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.