Photo by Saffron Blaze

Chepstow Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Chepstow holiday rentals

Fridge, electric kettle, toaster, cookware/dishes/utensils
The Snug

The Snug

The Snug
3.0 star property
Caerwent
The price is RM1,339
RM1,607 total
includes taxes & fees
5 Jan - 6 Jan
The Snug
Outdoor dining
Top Lodge

Top Lodge

Top Lodge
2.0 star property
Caerwent
The price is RM1,869
RM2,243 total
includes taxes & fees
5 Jan - 6 Jan
Top Lodge
Interior
The Comfy Cow

The Comfy Cow

The Comfy Cow
3.5 star property
Trellech United
The price is RM1,791
RM2,149 total
includes taxes & fees
6 Jan - 7 Jan
The Comfy Cow
Interior
The Honey Pot

The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is RM2,157
RM2,588 total
includes taxes & fees
5 Jan - 6 Jan
The Honey Pot
Private kitchen
Bottom Lodge

Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is RM1,869
RM2,243 total
includes taxes & fees
5 Jan - 6 Jan
Bottom Lodge
Room
Broadstone Park Camping & Fishery

Broadstone Park Camping & Fishery

Broadstone Park Camping & Fishery
1.0 star property
Coleford
9.8 out of 10, Exceptional, (23)
"Amazing place for work or holiday. Clean affordable and great staff"
United Kingdom
Luke
The price is RM273
RM328 total
includes taxes & fees
9 Jan - 10 Jan
Broadstone Park Camping & Fishery
Desk, laptop workspace, iron/ironing board, free WiFi
Newport Student Village - Campus Accommodation

Newport Student Village - Campus Accommodation

Newport Student Village - Campus Accommodation
4.0 star property
Pillgwenlly
8.2 out of 10, Very good, (216)
"Very happy with the price and quality of stay. Everything we needed for the weekend!"
United Kingdom
Joshua
The price is RM301
RM361 total
includes taxes & fees
2 Jan - 3 Jan
Newport Student Village - Campus Accommodation
Interior
Pentre Court Cottage

Pentre Court Cottage

Pentre Court Cottage
3.0 star property
Abergavenny
10.0 out of 10, Exceptional, (1)
"We had a fabulous stay, cannot fault it one bit. "
United Kingdom
Bethany
The price is RM2,896
RM3,475 total
includes taxes & fees
5 Jan - 6 Jan
Pentre Court Cottage
Living area
Cozy Studio Attic Retreat in Bettws Newydd

Cozy Studio Attic Retreat in Bettws Newydd

Cozy Studio Attic Retreat in Bettws Newydd
3.0 star property
Usk
10.0 out of 10, Exceptional, (3)
"Beautiful place. Nice grounds. Brand new. Quality finished by master craftsmen. Peaceful"
United Kingdom
Andrew
The price is RM571
RM571 total
includes taxes & fees
3 Jan - 4 Jan
Cozy Studio Attic Retreat in Bettws Newydd
Living area
Redmayne House

Redmayne House

Redmayne House
3.5 star property
Clifton
9.4 out of 10, Exceptional, (28)
"Fantastic property could not fault it will definitely stay again "
United Kingdom
Debra
The price is RM451
RM541 total
includes taxes & fees
4 Jan - 5 Jan
Redmayne House
1 bedroom, desk, laptop workspace, iron/ironing board
Your Apartment Clifton House

Your Apartment Clifton House

Your Apartment Clifton House
3.0 star property
Bristol
7.6 out of 10, Good, (96)
"Fantastic stay at a fantastic apartment! Would highly recommend."
United Kingdom
Montague Joshua Paul
Your Apartment Clifton House
Garden
De Courceys Manor Cottages

De Courceys Manor Cottages

De Courceys Manor Cottages
3.5 star property
Llanishen
9.2 out of 10, Wonderful, (33)
"Beautiful setting, very well looked after. The room was spotless it had everything you needed. A lovely welcome. We wanted to book in early as we had to be somewhere. The lovely lady on the phone arranged it no problem. I would highly recommend this place."
United Kingdom
David
The price is RM456
RM547 total
includes taxes & fees
6 Jan - 7 Jan
De Courceys Manor Cottages
1 bedroom
The Coach House and The Stable

The Coach House and The Stable

The Coach House and The Stable
3.5 star property
Stroud
9.0 out of 10, Wonderful, (41)
"Really lovely accommodation. Staff were very friendly and helpful and made sure check in and out was easy. We went to the pub for food and it was excellent - great menu and well cooked and presented. Staff were really helpful again Lovely area for a walk or trip to the vineyard "
United Kingdom
Helen
The price is RM342
RM410 total
includes taxes & fees
18 Jan - 19 Jan
The Coach House and The Stable
Interior
Pentre Barn

Pentre Barn

Pentre Barn
3.5 star property
Abergavenny
Pentre Barn
Dining
Lovely 1-bed Loft in Newport

Lovely 1-bed Loft in Newport

Lovely 1-bed Loft in Newport
3.0 star property
Caerleon
8.8 out of 10, Excellent, (3)
"Location very good for Caerleon. Clean and spacious "
United Kingdom
JAYNE
The price is RM385
RM462 total
includes taxes & fees
3 Jan - 4 Jan
Lovely 1-bed Loft in Newport
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

Bristol Marriott Royal Hotel

Bristol Marriott Royal Hotel

10/10 Excellent
"Location and hotel amenities"
Khrystyna 4-night trip
Posted 2 days ago
Bristol Marriott Royal Hotel

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
  • Use the map to find apartments and other holiday homes in the Chepstow neighbourhood you prefer
  • 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 close to the most popular sights in Chepstow, 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?

Cozy Blackwood Getaway - Peaceful Countryside Escape: This holiday home rental outside Chepstow offers a garden and free WiFi to help you feel comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Chepstow?

Choose from 7 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.