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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Chepstow holiday rentals

Interior

1. The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is S$813
includes taxes & fees
3 Aug - 4 Aug
The Honey Pot
Outdoor dining

2. Top Lodge

Top Lodge
2.0 star property
Caerwent
The price is S$704
includes taxes & fees
2 Aug - 3 Aug
Top Lodge
Fridge, electric kettle, toaster, cookware/dishes/utensils

3. The Snug

The Snug
3.0 star property
Caerwent
The price is S$504
includes taxes & fees
6 Aug - 7 Aug
The Snug
Living area

4. Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is S$704
includes taxes & fees
17 Aug - 18 Aug
Bottom Lodge
Exterior

5. Langford Apartments and Rooms

Langford Apartments and Rooms
3.5 star property
Bristol
8.0 out of 10, Very good, (1 review)
"I work nights so don’t really get to see anyone but all amenities are here,fair amount of road noise but that’s down to me working nights not the fault of property "
United Kingdom
Michael
The price is S$190
includes taxes & fees
13 Aug - 14 Aug
Langford Apartments and Rooms
Property entrance

6. Hillcroft Self Catering

Hillcroft Self Catering
3.5 star property
Bristol
9.8 out of 10, Exceptional, (54 reviews)
"Easy parking and super location for flying from Bristol. "
United Kingdom
Tanya
The price is S$325
includes taxes & fees
13 Aug - 14 Aug
Hillcroft Self Catering
Terrace/patio

7. 6 Newbridge Gardens

6 Newbridge Gardens
3.0 star property
Newbridge
The price is S$1,694
includes taxes & fees
12 Aug - 13 Aug
6 Newbridge Gardens
Front of property

8. Cottage Poppy

Cottage Poppy
2.0 star property
Keynsham
The price is S$306
includes taxes & fees
3 Aug - 4 Aug
Cottage Poppy
Private kitchen

9. The Old Bank - yourapartment

The Old Bank - yourapartment
4.0 star property
Brislington
8.0 out of 10, Very good, (5 reviews)
"It's not a bad place. But filthy carpets were the main disappointment & filthy smoke butts outside the main door up stairs. Was there for 3 days, not once did I see anybody do any cleaning or replenish towels or tea & coffee. That's why it wasn't value for money. The owner should put more effort into the place, instead of just taking the money."
Australia
Andre
The price is S$267
includes taxes & fees
31 Jul - 1 Aug
The Old Bank - yourapartment
Lounge

10. Orchard by UTDM

Orchard by UTDM
3.0 star property
Windmill Hill
The price is S$341
includes taxes & fees
17 Aug - 18 Aug
Orchard by UTDM
Gym

11. The Metalworks

The Metalworks
2.0 star property
Windmill Hill
8.0 out of 10, Very good, (17 reviews)
"Staff very helpful but check In was a faff and the room was incredibly hot"
United Kingdom
Amy
The price is S$141
includes taxes & fees
5 Aug - 6 Aug
The Metalworks
Living area

12. Waterside Living I Luxe Apartments

Waterside Living I Luxe Apartments
4.0 star property
Bristol Floating Harbour
9.0 out of 10, Wonderful, (2 reviews)
"Very spacious and clean with an outside patio with a great view of the busy harbour. Lots of shops/bars restaurants and activities for all ages in walking distance."
United Kingdom
Tina
The price is S$251
includes taxes & fees
31 Jul - 1 Aug
Waterside Living I Luxe Apartments
Lounge

13. Ideal Bristol Getaway - 3 bed Harbourside Home

Ideal Bristol Getaway - 3 bed Harbourside Home
2.0 star property
Bristol Floating Harbour
10.0 out of 10, Exceptional, (1 review)
"Good location, recently refurbished, perfect."
United Kingdom
ian
Ideal Bristol Getaway - 3 bed Harbourside Home
TV

14. PREMIER SUITES Bristol Redcliffe

PREMIER SUITES Bristol Redcliffe
4.0 star property
Bristol Floating Harbour
8.6 out of 10, Excellent, (184 reviews)
"Excellent location, very easy to access all attractions . Spacious apartment "
United Kingdom
Gareth
The price is S$153
includes taxes & fees
31 Jul - 1 Aug
PREMIER SUITES Bristol Redcliffe
Exterior

15. The Coach House

The Coach House
3.0 star property
Bristol
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful cottage in a great location. Owner is do friendly and helpful"
United Kingdom
Tanya
The price is S$533
includes taxes & fees
28 Aug - 29 Aug
The Coach House
Private kitchen

16. Hotwells Your Apartment

Hotwells Your Apartment
3.0 star property
Clifton
7.6 out of 10, Good, (9 reviews)
"All excelent"
United States
Juan Sebastian
The price is S$172
includes taxes & fees
31 Jul - 1 Aug
Hotwells 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

De Vere Tortworth Court

De Vere Tortworth Court

8/10 Good
"Good nice grounds, great food, lovely room. Only thing that was a let down was the spa. Tired and nothing special."
Neeraj 1-night trip
Posted 2 hours ago
De Vere Tortworth Court

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 11 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.