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Our top choices for Chepstow holiday rentals

Top Lodge

Top Lodge
2.0 star property
Caerwent
The price is £410
includes taxes & fees
11 Apr - 12 Apr
Top Lodge

The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is £473
includes taxes & fees
6 Apr - 7 Apr
The Honey Pot

The Snug

The Snug
3.0 star property
Caerwent
The price is £294
includes taxes & fees
13 Apr - 14 Apr
The Snug

Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is £410
includes taxes & fees
9 Apr - 10 Apr
Bottom Lodge

Hammonds Farmhouse

Hammonds Farmhouse
3.0 star property
Stroud
The price is £2,621
includes taxes & fees
27 Apr - 28 Apr
Hammonds Farmhouse

Tysylfaen Brecon Beacons

Tysylfaen Brecon Beacons
3.0 star property
Crickhowell
The price is £160
includes taxes & fees
9 Apr - 10 Apr
Tysylfaen Brecon Beacons

Riverfront Flat

Riverfront Flat
3.0 star property
Newport
The price is £195
includes taxes & fees
3 Apr - 4 Apr
Riverfront Flat

Cosy Oasis in the Heart of Clifton Village

Cosy Oasis in the Heart of Clifton Village
2.0 star property
Clifton
9.6 out of 10, Exceptional, (5 reviews)
"Ideally situated for culture, restaurants and shopping."
United Kingdom
Mrs Sandra
The price is £141
includes taxes & fees
6 Apr - 7 Apr
Cosy Oasis in the Heart of Clifton Village

The Orangery Apartment

The Orangery Apartment
4.0 star property
Bristol
9.6 out of 10, Exceptional, (69 reviews)
"Friendly welcome and the property had everything we needed."
United Kingdom
Michael
The price is £78
includes taxes & fees
6 Apr - 7 Apr
The Orangery Apartment

The Priory Cellars Abbots Leigh

The Priory Cellars Abbots Leigh
3.5 star property
Bristol
9.4 out of 10, Exceptional, (131 reviews)
"Awesome hosts and great accommodations!"
United States
Susan
The price is £80
includes taxes & fees
9 Apr - 10 Apr
The Priory Cellars Abbots Leigh

Cozy Cotswolds Retreat in Dursley

Cozy Cotswolds Retreat in Dursley
2.0 star property
Dursley
10.0 out of 10, Exceptional, (1 review)
"Appartamento molto confortevole, ben accessoriato e molto pulito. Le camere sono molto spaziose. Molto piacevole il soggiorno con camino. "
Italy
Gaetano
The price is £412
includes taxes & fees
10 Apr - 11 Apr
Cozy Cotswolds Retreat in Dursley

Lovely 1-bed Loft in Newport

Lovely 1-bed Loft in Newport
3.0 star property
Caerleon
9.0 out of 10, Wonderful, (4 reviews)
"Location very good for Caerleon. Clean and spacious "
United Kingdom
JAYNE
The price is £84
includes taxes & fees
6 Apr - 7 Apr
Lovely 1-bed Loft in Newport

The Old Sunday School

The Old Sunday School
3.5 star property
Lydney
The price is £840
includes taxes & fees
6 Apr - 7 Apr
The Old Sunday School

The Old Bank - yourapartment

The Old Bank - yourapartment
4.0 star property
Brislington
9.0 out of 10, Wonderful, (4 reviews)
"This flat had some things a business client would need in a self contained property, but the kitchen lacked some essentialslike and chopping board etc. However, post covid, i was surprised to see the unnecessary decorative items still laying about that others can touch etc. The property has some wear and tear issues that should be addressed, but nothing to stop you from staying here."
United Kingdom
Anonymous traveller
The price is £168
includes taxes & fees
5 Apr - 6 Apr
The Old Bank - yourapartment

Orchard by UTDM

Orchard by UTDM
3.0 star property
Windmill Hill
The price is £197
includes taxes & fees
9 Apr - 10 Apr
Orchard by UTDM

De Courceys Manor Cottages

De Courceys Manor Cottages
3.5 star property
Llanishen
9.2 out of 10, Wonderful, (35 reviews)
"Fab stay, cute little place "
United Kingdom
MARYA
The price is £89
includes taxes & fees
30 Apr - 1 May
De Courceys Manor Cottages

Quay Apartments Clarence House

Quay Apartments Clarence House
3.5 star property
St Julians
8.4 out of 10, Very good, (147 reviews)
"All good. "
United Kingdom
Ifeoluwa
The price is £81
includes taxes & fees
5 Apr - 6 Apr
Quay Apartments Clarence House

Ideal Bristol Getaway - 3 bed Harbourside Home

Ideal Bristol Getaway - 3 bed Harbourside Home
2.0 star property
Bristol Floating Harbour
The price is £344
includes taxes & fees
6 Apr - 7 Apr
Ideal Bristol Getaway - 3 bed Harbourside Home

Newport Student Village - Campus Accommodation

Newport Student Village - Campus Accommodation
4.0 star property
Pillgwenlly
8.2 out of 10, Very good, (219 reviews)
"I had a wonderful stay at Newport Student Village! It was only a short 10 minute walk to central Newport and if you walk 5 more minutes you will be at the bus station which will take you everywhere you need to go. The room lacked decoration but that was something I expected as the facility is used to house students. I did have a bathroom, so that was a pleasant surprise! The staff was incredibly helpful and polite. I would 100% stay here again! "
United Kingdom
Haley
The price is £59
includes taxes & fees
23 Apr - 24 Apr
Newport Student Village - Campus Accommodation

Old Fleece Apartments

Old Fleece Apartments
3.5 star property
Stroud
8.6 out of 10, Excellent, (40 reviews)
"Clean room comfy bed great staff "
United Kingdom
Alan
The price is £75
includes taxes & fees
19 Apr - 20 Apr
Old Fleece Apartments
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

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 £59 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. 

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?

Large Countryside House sleeps 17 stunning views ,hot tub and Games Rm: This highly rated holiday home rental in Chepstow offers a patio, a garden and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, an oven and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Chepstow?

Choose from 9 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.