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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Chepstow holiday rentals

Superior Cottage, Ensuite, Garden View (Skirrid) | Exterior

Welsh Marches at Upper Glyn Farm

Welsh Marches at Upper Glyn Farm
2.0 star property
Chepstow
10.0 out of 10, Exceptional, (6 reviews)
"Really enjoyed the tranquil location and area. Beautiful Wye Valley is nearby and Tintern Abbey too..... We loved it... Excellent facilities and cleanliness. Certainly re-charged our batteries "
United Kingdom
Shirley
Welsh Marches at Upper Glyn Farm
Fridge, electric kettle, toaster, cookware/dishes/utensils

The Snug

The Snug
3.0 star property
Caerwent
The price is ฿10,665
฿12,798 total
includes taxes & fees
30 Apr - 1 May
The Snug
Cottage | Interior

The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is ฿17,182
฿20,619 total
includes taxes & fees
5 May - 6 May
The Honey Pot
Cottage | Living area

Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is ฿14,886
฿17,864 total
includes taxes & fees
1 May - 2 May
Bottom Lodge
Outdoor dining

Top Lodge

Top Lodge
2.0 star property
Caerwent
The price is ฿14,886
฿17,864 total
includes taxes & fees
8 May - 9 May
Top Lodge
Cabin, Shared Bathroom (camping pod)

Broadstone Park Camping & Fishery

Broadstone Park Camping & Fishery
1.0 star property
Coleford
9.8 out of 10, Exceptional, (23 reviews)
"Amazing place for work or holiday. Clean affordable and great staff"
United Kingdom
Luke
The price is ฿2,178
฿2,614 total
includes taxes & fees
12 May - 13 May
Broadstone Park Camping & Fishery
Family Apartment | Living area

The Sixty 19 Stylish Studios and Apt.

The Sixty 19 Stylish Studios and Apt.
3.0 star property
Adamsdown
The price is ฿1,294
฿3,731 total
includes taxes & fees
30 Apr - 1 May
The Sixty 19 Stylish Studios and Apt.
Comfort Apartment, River View | Interior

Riverfront Flat

Riverfront Flat
3.0 star property
Newport
The price is ฿5,446
฿8,495 total
includes taxes & fees
28 Apr - 29 Apr
Riverfront Flat
Cottage | Property entrance

Beautiful 1-bed Cottage in Trellech

Beautiful 1-bed Cottage in Trellech
3.0 star property
Trellech United
9.2 out of 10, Wonderful, (24 reviews)
"Lovely staff and great space to relax."
United Kingdom
Eva
The price is ฿4,176
฿4,176 total
includes taxes & fees
29 Apr - 30 Apr
Beautiful 1-bed Cottage in Trellech
Desk, laptop workspace, iron/ironing board, free WiFi

Newport Student Village - Campus Accommodation

Newport Student Village - Campus Accommodation
4.0 star property
Pillgwenlly
8.2 out of 10, Very good, (221 reviews)
"It's a student halls of residence. If that's what you're expecting I would imagine you'd be very happy with the room. If you're expecting a hotel, it's not a hotel. It was exactly as I was expecting. Comfortable, no frills, perfectly fine for a one night stay for me. Wifi was great. A little bit of noise at times, it's student accommodation, but not too noisy by a long way. I recently stayed at the IBIS in Bristol and that was far noisier. Would happily book again for a short stay."
United Kingdom
Christopher
The price is ฿2,396
฿2,875 total
includes taxes & fees
28 Apr - 29 Apr
Newport Student Village - Campus Accommodation
Living area

Grandads Shack

Grandads Shack
2.0 star property
Pontypool
10.0 out of 10, Exceptional, (1 review)
"A lovely caravan thats been lovingly maintained"
United Kingdom
Chris
The price is ฿13,701
฿16,442 total
includes taxes & fees
1 May - 2 May
Grandads Shack
Exterior

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 ฿3,449
฿4,139 total
includes taxes & fees
28 Apr - 29 Apr
De Courceys Manor Cottages
Property grounds

The Priory Cellars Abbots Leigh

The Priory Cellars Abbots Leigh
3.5 star property
Bristol
9.4 out of 10, Exceptional, (132 reviews)
"Awesome hosts and great accommodations!"
United States
Susan
The price is ฿3,311
฿3,311 total
includes taxes & fees
28 Apr - 29 Apr
The Priory Cellars Abbots Leigh
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

Majestic Hotels Bristol

Majestic Hotels Bristol

10/10 Excellent
"Great location . Room clean and comfortable Staff really friendly and helpful ."
Lisa 1-night trip
Posted 1 hour ago
Majestic Hotels Bristol

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
  • 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 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?

No 2 Georgian Shared House \- By Clifton Short Lets: This holiday home rental outside of Chepstow offers a garden and free WiFi to help you feel comfortable in your new surroundings.

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.