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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chepstow holiday rentals

A modern kitchen with white cabinetry, a built-in oven, and a dining area with a wooden table and chairs.

1. New 3 Bedroom Apartment Next to Station

New 3 Bedroom Apartment Next to Station
Chepstow
The price is HK$1,614
HK$1,749 total
includes taxes & fees
13 Dec - 14 Dec
New 3 Bedroom Apartment Next to Station
A modern kitchen with a built-in oven and a dining area with a table and chairs.

2. The Long Weekend

The Long Weekend
Chepstow
The price is HK$8,330
HK$9,048 total
includes taxes & fees
15 Nov - 16 Nov
The Long Weekend
A hot tub in an outdoor wooden enclosure with a tiled floor and a wicker chair nearby.

3. The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is HK$4,305
HK$5,166 total
includes taxes & fees
23 Nov - 24 Nov
The Honey Pot
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 HK$2,799
HK$3,359 total
includes taxes & fees
19 Nov - 20 Nov
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 HK$3,907
HK$4,688 total
includes taxes & fees
21 Nov - 22 Nov
Bottom Lodge
A hot tub with a wooden deck, outdoor seating, and a view of the countryside.

6. Top Lodge

Top Lodge
3.0 star property
Caerwent
The price is HK$3,907
HK$4,688 total
includes taxes & fees
16 Nov - 17 Nov
Top Lodge
A stone wall entrance to a building with a black door and a small trash bin.

7. 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 HK$943
HK$943 total
includes taxes & fees
22 Nov - 23 Nov
Beautiful 1-bed Cottage in Trellech
A bedroom with a bed, a wooden wardrobe, and a bedside table.

8. Livin' Serviced Apartments - Newport

Livin' Serviced Apartments - Newport
2.0 star property
St Julians
10.0 out of 10, Exceptional, (3 reviews)
"Great apartment. Very spacious. Absolutely loved staying here. Will definitely do it again"
United Kingdom
Lucy
The price is HK$445
HK$534 total
includes taxes & fees
16 Nov - 17 Nov
Livin' Serviced Apartments - Newport
Interior

9. 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 HK$1,031
HK$1,406 total
includes taxes & fees
16 Nov - 17 Nov
A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.
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.

10. Bilsham Meadows

Bilsham Meadows
3.0 star property
Bristol
Bilsham Meadows
A narrow stone corridor with a small table and chairs, a door, and a window with a view into a room.

11. 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 HK$791
HK$791 total
includes taxes & fees
15 Nov - 16 Nov
The Priory Cellars Abbots Leigh
A modern kitchen with a stainless steel sink, a round mirror, and a potted plant.

12. 526 Gloucester Flat 1 - Hopewell

526 Gloucester Flat 1 - Hopewell
Horfield
9.6 out of 10, Exceptional, (4 reviews)
"I loved the independence of the flat. The kitchen was fab but could have done with a microwave or even an oven dish. I did not like seeing all the bins at the front full to the brim. Loved the shower and the bed was okay but badly needed a bedside light. A small chest of drawers would also of been handy. I would book again. "
United Kingdom
Vanessa
The price is HK$614
HK$1,031 total
includes taxes & fees
1 Dec - 2 Dec
526 Gloucester Flat 1 - Hopewell
A neatly made bed with pillows and folded towels, a wooden dresser, a window with curtains, and a view of the outside.

13. 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 HK$1,484
HK$1,781 total
includes taxes & fees
15 Nov - 16 Nov
Your Stay Bristol Orchard Gate
A marina at dusk with boats docked, buildings in the background, and a calm water surface reflecting the lights.

14. Stylish Marina Apartment with Stunning Views

Stylish Marina Apartment with Stunning Views
Portishead
9.6 out of 10, Exceptional, (4 reviews)
"Lovely place to stay ver clean & comfy"
United Kingdom
Carol D.
The price is HK$890
HK$1,307 total
includes taxes & fees
15 Nov - 16 Nov
Stylish Marina Apartment with Stunning Views
A historic building with a classical architectural style, featuring a prominent entrance with a sign for Belvilla City Centre.

15. Belvilla Newport City Centre Hotel - Deluxe Double Room

Belvilla Newport City Centre Hotel - Deluxe Double Room
Newport City Centre
9.4 out of 10, Exceptional, (205 reviews)
"The staff here are the best! So friendly and helpful. The breakfast was excellent, and I loved the variety. The location is perfect for exploring the city."
United States
Anonymous traveller
The price is HK$483
HK$483 total
includes taxes & fees
22 Nov - 23 Nov
Belvilla Newport City Centre Hotel - Deluxe Double Room
A row of traditional terraced houses with a narrow street in front.

16. Bright & Beautiful Studio Flat in Bristol

Bright & Beautiful Studio Flat in Bristol
3.0 star property
Bristol
10.0 out of 10, Exceptional, (2 reviews)
"Was a beautiful walks away from Bristol City Centre, but transportation is very easily accessible to get to most places. Very quiet, beautiful and was perfect for my holiday! "
United States
Katarina
Bright & Beautiful Studio Flat in Bristol
A conservatory with stone arches, potted plants, and a bench.

17. The Orangery Apartment

The Orangery Apartment
4.0 star property
Bristol
9.6 out of 10, Exceptional, (85 reviews)
"The apartment was so roomy . Space to park and a great little pub at the end of the road . Nick was an excellent host !"
Australia
Narelle
The price is HK$833
HK$833 total
includes taxes & fees
16 Nov - 17 Nov
The Orangery Apartment
House

18. 2 bedroom accommodation in Lydney

2 bedroom accommodation in Lydney
Lydney
9.8 out of 10, Exceptional, (30 reviews)
"If you're looking for a comfortable cozy relaxed break, this is where to come.Absolutely perfect!"
United States
Lorraine Galea
The price is HK$2,051
HK$2,051 total
includes taxes & fees
26 Nov - 27 Nov
2 bedroom accommodation in Lydney
A gravel driveway leading to a stone wall and a building with ivy-covered walls.

19. 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 HK$7,809
HK$8,924 total
includes taxes & fees
16 Nov - 17 Nov
HartHill Grange Bunkhouse - Unique 1850's Rural Country Accommodation
A stone house with a sloped roof, a wooden gate, and a stone wall.

20. The Pound

The Pound
3.0 star property
Trellech United
10.0 out of 10, Exceptional, (4 reviews)
"We really loved it there the host was very friendly enjoed the weekend very much"
United Kingdom
Kevin
The price is HK$3,090
HK$3,709 total
includes taxes & fees
20 Nov - 21 Nov
The Pound
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

Celtic Manor Resort

Celtic Manor Resort

10/10 Excellent
"Loved it great golf staff very friendly everything you need and good food"
Tate 2-night trip
Posted 2 hours ago
Celtic Manor Resort

Find out more about Chepstow

Search for holiday rentals in Chepstow on Expedia! 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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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.