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

Holiday Rentals 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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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 €552
includes taxes & fees
29 Sept - 30 Sept
The Honey Pot
A hot tub with a wooden deck, outdoor seating, and a view of the countryside.

2. Top Lodge

Top Lodge
2.0 star property
Caerwent
Top Lodge
A stone wall, a patterned metal fence, and a building with a tiled roof.

3. Ferryman's Lodge

Ferryman's Lodge
2.0 star property
Chepstow
The price is €398
includes taxes & fees
8 Oct - 9 Oct
Ferryman's Lodge
A modern kitchen with white cabinets, a stainless steel oven, a sink, and a yellow toaster.

4. The Snug

The Snug
3.0 star property
Caerwent
The price is €342
includes taxes & fees
14 Oct - 15 Oct
The Snug
A modern living room with a sofa, armchair, coffee table, and a painting of red buses.

5. Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is €477
includes taxes & fees
11 Oct - 12 Oct
Bottom 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.

6. Bilsham Meadows

Bilsham Meadows
3.0 star property
Bristol
The price is €1,692
includes taxes & fees
28 Sept - 29 Sept
Bilsham Meadows
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 €70
includes taxes & fees
8 Oct - 9 Oct
Broadstone Park Camping & Fishery
A narrow stone corridor with a small table and chairs, a door, and a window with a view into a room.

8. 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 €89
includes taxes & fees
27 Sept - 28 Sept
The Priory Cellars Abbots Leigh
A stone wall entrance to a building with a black door and a small trash bin.

9. 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 €105
includes taxes & fees
8 Oct - 9 Oct
Beautiful 1-bed Cottage in Trellech
A spacious lobby with a large sofa, patterned chairs, a wooden coffee table, and a large window offering a view of the street.

10. Orchard by UTDM

Orchard by UTDM
3.0 star property
Windmill Hill
The price is €211
includes taxes & fees
29 Sept - 30 Sept
Orchard by UTDM
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, (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 €93
includes taxes & fees
6 Oct - 7 Oct
The Orangery Apartment
A modern kitchen with built-in appliances, a dining area with a table and chairs, and a living space with a sofa and coffee table.

12. The Sixty 19 Stylish Studios and Apt.

The Sixty 19 Stylish Studios and Apt.
3.0 star property
Adamsdown
The price is €127
includes taxes & fees
11 Oct - 12 Oct
The Sixty 19 Stylish Studios and Apt.
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.

13. 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 €82
includes taxes & fees
21 Oct - 22 Oct
Quay Apartments Clarence House
A bedroom with a wooden headboard, a bed with a gray blanket, a pillow with a floral design, and a cat on the bed.

14. 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 €176
includes taxes & fees
4 Oct - 5 Oct
Higgihaus 26 Clare Street Aparthotel
A living room with a sofa, coffee table, TV, and a fruit bowl.

15. PREMIER SUITES Bristol Redcliffe

PREMIER SUITES Bristol Redcliffe
4.0 star property
Bristol Floating Harbour
8.6 out of 10, Excellent, (193 reviews)
"Great flat Stayed for o e night so only used for the night Well equipped"
United Kingdom
rasiah
The price is €104
includes taxes & fees
4 Oct - 5 Oct
PREMIER SUITES Bristol Redcliffe
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.

16. Hidden Well

Hidden Well
2.5 star property
Bristol
The price is €1,541
includes taxes & fees
28 Sept - 29 Sept
Hidden Well
A bedroom with a large bed, wooden floor, a bedside table with a lamp, and two wall-mounted artworks.

17. Your Stay Bristol Hamilton Court

Your Stay Bristol Hamilton Court
4.0 star property
Stokes Croft
9.0 out of 10, Wonderful, (112 reviews)
"Place is convenient, comfortable and safe"
Singapore
Tan
The price is €205
includes taxes & fees
27 Sept - 28 Sept
Your Stay Bristol Hamilton Court
A cozy room with a bed, a small table, a sofa, and a view of the outdoors.

18. The Coach House and The Stable

The Coach House and The Stable
3.5 star property
Stroud
8.8 out of 10, Excellent, (47 reviews)
"Great stay "
United Kingdom
Tania
The price is €99
includes taxes & fees
6 Oct - 7 Oct
The Coach House and The Stable
A traditional building with a sign reading "Welcome to The Olde Bull Inn" at night.

19. 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 €98
includes taxes & fees
25 Oct - 26 Oct
Lovely 1-bed Loft in Newport
A modern kitchen with white cabinets, a stainless steel range hood, a microwave, and a built-in oven.

20. 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 €283
includes taxes & fees
2 Oct - 3 Oct
The Old Bank - yourapartment
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

The Coach & Horses Hotel

The Coach & Horses Hotel

10/10 Excellent
"Clean and tidy hotel, a pleasant stay"
Alex 1-night trip
Posted 4 hours ago
The Coach & Horses Hotel

Find out more about Chepstow

Everything you need to know about Chepstow holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chepstow holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chepstow holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chepstow holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chepstow. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chepstow holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chepstow holiday rentals we have selected for you start as low as €70 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chepstow rentals

At Expedia, we put the best Chepstow holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chepstow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chepstow holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chepstow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

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 13 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.