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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chepstow holiday rentals

A hot tub in an outdoor wooden enclosure with a tiled floor and a wicker chair nearby.

1. The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is RM2,127
RM2,553 total
includes taxes & fees
17 Oct - 18 Oct
The Honey Pot
A modern living room with a sofa, armchair, coffee table, and a painting of red buses.

2. Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is RM1,843
RM2,212 total
includes taxes & fees
22 Oct - 23 Oct
Bottom Lodge
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 RM1,320
RM1,584 total
includes taxes & fees
23 Oct - 24 Oct
The Snug
A hot tub with a wooden deck, outdoor seating, and a view of the countryside.

4. Top Lodge

Top Lodge
2.0 star property
Caerwent
The price is RM1,843
RM2,212 total
includes taxes & fees
18 Oct - 19 Oct
Top Lodge
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.

5. Bilsham Meadows

Bilsham Meadows
3.0 star property
Bristol
The price is RM6,524
RM7,829 total
includes taxes & fees
19 Oct - 20 Oct
Bilsham Meadows
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 RM488
RM488 total
includes taxes & fees
18 Oct - 19 Oct
Beautiful 1-bed Cottage in Trellech
A living room with a sofa, coffee table, TV, and a fruit bowl.

7. PREMIER SUITES Bristol Redcliffe

PREMIER SUITES Bristol Redcliffe
4.0 star property
Bristol Floating Harbour
8.6 out of 10, Excellent, (194 reviews)
"Great flat Stayed for o e night so only used for the night Well equipped"
United Kingdom
rasiah
The price is RM400
RM480 total
includes taxes & fees
18 Oct - 19 Oct
PREMIER SUITES Bristol Redcliffe
A modern kitchen with a built-in oven, a dining area with a round table and chairs, and large windows with a view of a bridge.

8. Quay Apartments Clarence House

Quay Apartments Clarence House
3.5 star property
St Julians
8.4 out of 10, Very good, (158 reviews)
"Fast and easy check-in, helpful staff and quick production of a VAT invoice for expenses. The apartment was clean, roomy and comfortable, with a good bed, large TV, well equipped kitchen and great shower too. Parking is very convenient and placed at the back of the building in the multi-storey car park. Local supermarket very close too. Great."
United Kingdom
Andrew
The price is RM307
RM369 total
includes taxes & fees
14 Oct - 15 Oct
Quay Apartments Clarence House
A two-story brick building with a black door and windows, parked cars in front, and trees with green leaves.

9. Your Stay Bristol Beaufort House

Your Stay Bristol Beaufort House
4.0 star property
Clifton
9.8 out of 10, Exceptional, (36 reviews)
"Gorgeous apartment beautifully set out - loved it - parking good - would recommend"
United Kingdom
Amy
The price is RM809
RM971 total
includes taxes & fees
15 Oct - 16 Oct
Your Stay Bristol Beaufort House
A modern kitchen with a central island, white cabinetry, and a dining area with a table and chairs.

10. Frederick Place Your Apartment

Frederick Place Your Apartment
4.5 star property
Clifton
7.4 out of 10, Good, (12 reviews)
"Beautiful, spacious apartment in a fantastic location, cant recommend enough"
United Kingdom
Roger
The price is RM962
RM1,154 total
includes taxes & fees
23 Oct - 24 Oct
Frederick Place Your Apartment
A conservatory with stone arches, potted plants, and a bench.

11. The Orangery Apartment

The Orangery Apartment
4.0 star property
Bristol
9.6 out of 10, Exceptional, (81 reviews)
"Wonderful property and hosts. Great parking and facilities in property with plenty of space and stocked kitchen facilities. Would stay again"
United Kingdom
Janet
The price is RM432
RM432 total
includes taxes & fees
14 Oct - 15 Oct
The Orangery Apartment
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, (144 reviews)
"Nice place to stay for a few nights and very well equipped"
United Kingdom
John
The price is RM410
RM410 total
includes taxes & fees
1 Nov - 2 Nov
The Priory Cellars Abbots Leigh
A modern living room with a large window, a sofa, a coffee table, and a TV mounted on the wall.

13. Waterside Living I Luxe Apartments

Waterside Living I Luxe Apartments
4.0 star property
Bristol Floating Harbour
9.4 out of 10, Exceptional, (3 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 RM845
RM1,014 total
includes taxes & fees
16 Oct - 17 Oct
Waterside Living I Luxe Apartments
A spacious living room with a large sofa set, a wooden coffee table, and a television. There is a large sliding glass door leading to a patio with a view of the outdoors.

14. Hidden Well

Hidden Well
2.5 star property
Bristol
The price is RM5,942
RM7,130 total
includes taxes & fees
19 Oct - 20 Oct
Hidden Well
A compact kitchen with a microwave, toaster, and coffee maker. A bed with a headboard is visible in the background.

15. Hotwells Your Apartment

Hotwells Your Apartment
3.0 star property
Clifton
7.4 out of 10, Good, (11 reviews)
"Small clean room cosy and warm bus stop right outside the apartments but very noisy you can hear every move of other residents in the property"
Ireland
Hoa Minh
The price is RM526
RM631 total
includes taxes & fees
14 Oct - 15 Oct
Hotwells Your Apartment
A traditional building with a sign reading "Welcome to The Olde Bull Inn" at night.

16. 1 Bed Loft - Sleeps 2 - Parking - Wifi

1 Bed Loft - Sleeps 2 - Parking - Wifi
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 RM383
RM460 total
includes taxes & fees
16 Oct - 17 Oct
1 Bed Loft - Sleeps 2 - Parking - Wifi
A modern kitchen with wooden cabinets, a dining table with chairs, and large windows with curtains.

17. 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, (220 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 RM400
RM480 total
includes taxes & fees
18 Oct - 19 Oct
PREMIER SUITES PLUS Bristol Cabot Circus
A bedroom with a wooden headboard, a bed with a gray blanket, a pillow with a floral design, and a cat on the bed.

18. 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)
The price is RM510
RM845 total
includes taxes & fees
18 Oct - 19 Oct
Higgihaus 26 Clare Street Aparthotel
A modern bedroom with a large bed, a bedside table with a lamp, and a view of the city through a window.

19. Colston Street - Your Apartment

Colston Street - Your Apartment
3.0 star property
Bristol
8.6 out of 10, Excellent, (9 reviews)
"I enjoyed it highly recommended.....will do it anytime again.....perfect for a get away peace quiet an great....."
United Kingdom
Sansha
The price is RM773
RM928 total
includes taxes & fees
23 Oct - 24 Oct
Colston Street - Your Apartment
A multi-story building with a stone facade, large windows, and a corner entrance.

20. Your Apartment - Pembroke House

Your Apartment - Pembroke House
4.0 star property
Clifton
8.4 out of 10, Very good, (7 reviews)
"Great location in Clifton. Combination washer and dryer worked well. Kitchen was well equipped. Bedroom was in need of a vacuum and mattress was a bit soft for our liking."
Canada
Michele
The price is RM663
RM796 total
includes taxes & fees
6 Nov - 7 Nov
Your Apartment - Pembroke House
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

10/10 Excellent
"Lovely room comforting bed and large tv very nice grounds"
Matthew 1-night trip
Posted 6 hours ago
De Vere Tortworth Court

Find out more about Chepstow

Search for holiday rentals in Chepstow on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Chepstow using one of the methods below:

  • View our selection of featured holiday rentals in Chepstow
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  • Enter your travel dates to view the best deals on holiday rentals in Chepstow while they last

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 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.