Vacation rentals in Chepstow

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Top-rated accommodation in Chepstow

Guests agree: these stays are highly rated for location, cleanliness and more.

Superhost

Cottage in Chepstow

4.84 out of 5 average rating, 353 reviews

Pineapple Cottage - Chepstow Town Centre (Wales)

17th Century cottage in the heart of Chepstow, close to Offa's Dyke & the Wye Valley. Tucked down a little cobbled street in the town centre, it’s a small but perfectly formed cottage ideal for a couple or a young family. There’s a secret door leading to the second bedroom, where you’ll even get a glimpse of Chepstow Castle from the window. It’s an ideal base for weddings at St Tewdrics (we’ve even hosted the bride and groom!) or for walking and cycling in the Forest of Dean and Wye Valley.

22 – 29 Sept

$1,167 AUD total
Guest favourite

Townhouse in Chepstow

4.94 out of 5 average rating, 162 reviews

Chepstow Town. Welsh Cottage.

The house is in the centre of the beautiful old market town of Chepstow. Nestled on the Welsh / English border. We are just a stone's throw from the ancient castle and the impressive Priory Church of St Mary. Within walking distance of the Chepstow Racecourse and a stroll from the railway and bus stations. 300yds from the River Wye and central to all restaurants and cafes etc. Situated near the AONB Wye Valley and Forest of Dean. Please note the property has a Jack & Jill bathroom upstairs.

23 – 30 Sept

$1,109 AUD total
Guest favourite

Chalet in Boughspring

4.87 out of 5 average rating, 117 reviews

The Studio

A refurbished stone built, 1 bedroom detached chalet in an extremely quiet rural location close to good traffic links, long-distance footpath, Forest of Dean, Wye Valley and the National Dive Centre. Large lounge with log burner, sofa and dining table. Open plan kitchen with electric oven, induction hob, microwave, fridge and toaster. One bedroom with king size bed, ensuite shower and wc. Private patio and access to garden. 5 min drive to shops in Chepstow, 40mins to Bristol / Cardiff.

5 – 12 Aug

$1,165 AUD total

Popular amenities for Chepstow accommodation

Stay near Chepstow's top sights

Panevino Italian Restaurant18 locals recommend
Coffee#1 Chepstow3 locals recommend
Lime Tree5 locals recommend
The Three Tuns6 locals recommend
M&S Chepstow Foodhall6 locals recommend
Stone Rock Pizza15 locals recommend

Other great accommodation in Chepstow

Guest favourite

Apartment in Gloucestershire

5.0 out of 5 average rating, 107 reviews

Idyllic Country Retreat in the Forest of Dean

26 Nov – 3 Dec

$1,082 AUD total
Guest favourite

Guest suite in Tockington

4.95 out of 5 average rating, 323 reviews

The Dairy - Quaint village stay

6 – 13 Oct

$966 AUD total
Guest favourite

Home in Soudley

4.98 out of 5 average rating, 382 reviews

The Zion Chapel

5 – 12 Feb

$1,404 AUD total
Guest favourite

Cottage in Upper Redbrook

4.95 out of 5 average rating, 292 reviews

Country cottage in the Wye Valley & Forest of Dean

8 – 15 Feb

$1,211 AUD total
Guest favourite

Cottage in Monmouthshire

5.0 out of 5 average rating, 23 reviews

Historic cottage opposite Chepstow Castle

23 – 30 Sept

$1,684 AUD total
Guest favourite

Condo in Monmouthshire

4.86 out of 5 average rating, 21 reviews

Spacious Chepstow town apartment

15 – 20 Apr

$813 AUD total
Guest favourite

Guesthouse in Monmouthshire

4.99 out of 5 average rating, 77 reviews

The coachouse.

25 Aug – 1 Sept

$1,660 AUD total
Guest favourite

Condo in Monmouthshire

5.0 out of 5 average rating, 46 reviews

Castle House Apartment 2 Georgian town house

1 – 8 Sept

$1,643 AUD total
Guest favourite

Condo in Tidenham

4.96 out of 5 average rating, 89 reviews

Annexe with stunning views over the River Severn

9 – 16 Apr

$990 AUD total
Guest favourite

Home in Tidenham Chase

4.93 out of 5 average rating, 15 reviews

The Dairy - Wye Valley Area of outstanding beauty

13 – 20 Aug

$889 AUD total
Guest favourite

Home in Bulwark

5.0 out of 5 average rating, 24 reviews

Modern, Newly Built, Two Double Bedroom House

26 Nov – 3 Dec

$1,413 AUD total
Guest favourite

Cottage in Chepstow

4.97 out of 5 average rating, 36 reviews

Charming 3BR Chepstow cottage w/parking & garden.

30 Jan – 6 Feb

$2,577 AUD total

Quick stats about holiday rentals in Chepstow

Total rentals

20 properties

Local attractions

Panevino Italian Restaurant, Lidl Chepstow and Coffee#1 Chepstow

Popular amenities

Kitchen, Wi-Fi and Pool

Wi-Fi availability

20 properties include access to Wi-Fi

Total number of reviews

1.4K reviews

Nightly prices starting at

$15 AUD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United Kingdom
  3. Wales
  4. Monmouthshire
  5. Chepstow