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

Holiday Homes 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
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Chepstow holiday homes

A modern kitchen with a built-in oven and a dining area with a table and chairs.

1. The Long Weekend

The Long Weekend
Chepstow
The price is €1,026
includes taxes & fees
15 Nov - 16 Nov
The Long Weekend
Interior

2. 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 €165
includes taxes & fees
9 Nov - 10 Nov
A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.
A neatly made bed with a headboard, a bedside lamp, and a potted plant.

3. Bristol Gateway Family Home

Bristol Gateway Family Home
Stoke Gifford
The price is €250
includes taxes & fees
7 Dec - 8 Dec
Bristol Gateway Family Home
A gravel driveway leading to a stone wall and a building with ivy-covered walls.

4. 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 €1,027
includes taxes & fees
9 Nov - 10 Nov
HartHill Grange Bunkhouse - Unique 1850's Rural Country Accommodation
A modern kitchen with grey cabinets, a stainless steel range hood, a built-in oven, and a large refrigerator.

5. Anstey Heights - Apartment 7 - Hopewell

Anstey Heights - Apartment 7 - Hopewell
Easton
10.0 out of 10, Exceptional, (1 review)
"Nice clean flat in a well-organised apartment building (10 apartments), it is quiet inside the house and the neighbourhood is lively but friendly with a well-equipped little corner shop. It’s only a short walk to bus stops and the bicycle and foot path that takes you either to the city centre or outside of Bristol. Tip: the Garden of Easton is nearby, an amazing café / restaurant full of plants inside and outside."
United States
Anja P.
Anstey Heights - Apartment 7 - Hopewell
A modern bedroom with a large bed, bedside tables, a mirror, and a hanging light fixture.

6. Spacious Open-Plan Modern House w/ Garden&Parking

Spacious Open-Plan Modern House w/ Garden&Parking
Filton
7.4 out of 10, Good, (3 reviews)
"Lovely spacious"
United States
Melanie H.
The price is €677
includes taxes & fees
9 Dec - 10 Dec
Spacious Open-Plan Modern House w/ Garden&Parking
A neatly made bed with a white and yellow bedspread, a wooden nightstand with a lamp, and a gray headboard.

7. Eden Homez

Eden Homez
2.0 star property
Bristol
2.0 out of 10, (1 review)
"They cancelled the booking 2 hours before check-in and haven't refunded me"
United Kingdom
ant
The price is €207
includes taxes & fees
9 Nov - 10 Nov
Eden Homez
A staircase with beige carpet, white walls, and wooden flooring.

8. Entire 5 Bed home in Bristol United Kingdom

Entire 5 Bed home in Bristol United Kingdom
Pucklechurch
Entire 5 Bed home in Bristol United Kingdom
A compact hotel room with a kitchenette, a bed, a bedside table, and a window.

9. Prince Street Studio 4 - Hopewell

Prince Street Studio 4 - Hopewell
Bristol City Centre
Prince Street Studio 4 - Hopewell
decking, patio furniture and secluded quiet garden

10. Quiet central location, comfortable, homely and relaxed

Quiet central location, comfortable, homely and relaxed
Roath
The price is €131
includes taxes & fees
10 Nov - 11 Nov
Quiet central location, comfortable, homely and relaxed
A hot tub in a backyard with string lights and a wooden fence.

11. Cosy house with a hot tub, sleeps 9, free parking, wifi

Cosy house with a hot tub, sleeps 9, free parking, wifi
Griffithstown
Cosy house with a hot tub, sleeps 9, free parking, wifi
Exterior detail

12. Two Bedroom Flat on Christmas Steps

Two Bedroom Flat on Christmas Steps
Bristol Floating Harbour
The price is €195
includes taxes & fees
2 Dec - 3 Dec
Two Bedroom Flat on Christmas Steps
A dining area with a table set for four, a television above the table, and a staircase leading to another level.

13. Y Ddraig Suite by NextStep Stays - City Centre - Sleeps 8 - Free Parking

Y Ddraig Suite by NextStep Stays - City Centre - Sleeps 8 - Free Parking
Adamsdown
10.0 out of 10, Exceptional, (1 review)
"Seamless check in.Great communication Handy for centre of Cardiff"
United States
Colette W.
The price is €232
includes taxes & fees
10 Nov - 11 Nov
Y Ddraig Suite by NextStep Stays - City Centre - Sleeps 8 - Free Parking
A modern kitchen with a microwave, a dining area with stools, a sofa, and a television.

14. Grange Rd Flat 5 one bedroom

Grange Rd Flat 5 one bedroom
Clifton
Grange Rd Flat 5 one bedroom
A modern dining area with a wooden table set for breakfast, including croissants, fruit, and orange juice.

15. Woodland View Newport - 4 bedroom home

Woodland View Newport - 4 bedroom home
4.0 star property
Beechwood
Woodland View Newport - 4 bedroom home
A living room with a grey sofa, a coffee table, a fireplace, a TV, and a floor lamp.

16. Spacious Newport Home Near ICC & Local Attractions

Spacious Newport Home Near ICC & Local Attractions
Beechwood
Spacious Newport Home Near ICC & Local Attractions
A sunlit room with a sliding glass door, a cushioned chair, a small table, and a view of trees and a building outside.

17. Chic Stay btwn Bath&Bristol | Sleeps 9 | Drummond

Chic Stay btwn Bath&Bristol | Sleeps 9 | Drummond
Longwell Green
The price is €247
includes taxes & fees
7 Dec - 8 Dec
Chic Stay btwn Bath&Bristol | Sleeps 9 | Drummond
A modern kitchen with a brick wall, wooden flooring, and a large refrigerator.

18. 4 Bed Townhouse-sleeps 7-garden-pets-valley View

4 Bed Townhouse-sleeps 7-garden-pets-valley View
3.5 star property
Aberbeeg
The price is €347
includes taxes & fees
10 Nov - 11 Nov
4 Bed Townhouse-sleeps 7-garden-pets-valley View
A corner building with a barber shop on the ground floor, a blue door, and a parked car.

19. Stylish Bristol Holiday Home for 8

Stylish Bristol Holiday Home for 8
Clifton
10.0 out of 10, Exceptional, (10 reviews)
"Parking just outside made getting around Bristol easier than expected. For what you get here compared to others nearby, it feels worth every penny, spacious rooms and a convenient location add extra value."
United States
Anonymous traveller
Stylish Bristol Holiday Home for 8
A kitchen with a stone wall, a fireplace, a dining table with chairs, a sofa, and a door with a window.

20. One Bedroom Cottage in Chew Stoke

One Bedroom Cottage in Chew Stoke
Chew Stoke
The price is €157
includes taxes & fees
7 Dec - 8 Dec
One Bedroom Cottage in Chew Stoke
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

Holland House Hotel Cardiff By Sunday

Holland House Hotel Cardiff By Sunday

8/10 Good
"Great"
Ifeoluwa 1-night trip
Posted 14 hours ago
Holland House Hotel Cardiff By Sunday

Find out more about Chepstow

Chepstow Holiday Homes information

Number of reviews
62
Accommodation
742 Holiday Homes
Lowest Price
€131
Highest Price
€1,027

Explore a world of travel with Expedia