Vacation rentals in Chepstow

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Top-rated vacation rentals in Chepstow

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

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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.

Sep 22 – 29

ﺩ.ﺇ386 per night
Guest favorite

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.

Sep 23 – 30

ﺩ.ﺇ366 per night
Guest favorite

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.

Aug 5 – 12

ﺩ.ﺇ380 per night

Popular amenities for Chepstow vacation rentals

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 vacation rentals in Chepstow

Guest favorite

Apartment in Gloucestershire

5.0 out of 5 average rating, 107 reviews

Idyllic Country Retreat in the Forest of Dean

Nov 26 – Dec 3

ﺩ.ﺇ347 per night
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Guest suite in Tockington

4.95 out of 5 average rating, 323 reviews

The Dairy - Quaint village stay

Oct 6 – 13

ﺩ.ﺇ320 per night
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Home in Soudley

4.98 out of 5 average rating, 382 reviews

The Zion Chapel

Feb 5 – 12

ﺩ.ﺇ481 per night
Guest favorite

Cottage in Upper Redbrook

4.95 out of 5 average rating, 292 reviews

Country cottage in the Wye Valley & Forest of Dean

Feb 8 – 15

ﺩ.ﺇ395 per night
Guest favorite

Cottage in Monmouthshire

5.0 out of 5 average rating, 23 reviews

Historic cottage opposite Chepstow Castle

Sep 23 – 30

ﺩ.ﺇ556 per night
Guest favorite

Condo in Monmouthshire

4.86 out of 5 average rating, 21 reviews

Spacious Chepstow town apartment

Apr 15 – 20

ﺩ.ﺇ363 per night
Guest favorite

Guesthouse in Monmouthshire

4.99 out of 5 average rating, 77 reviews

The coachouse.

Aug 25 – Sep 1

ﺩ.ﺇ568 per night
Guest favorite

Condo in Monmouthshire

5.0 out of 5 average rating, 46 reviews

Castle House Apartment 2 Georgian town house

Sep 1 – 8

ﺩ.ﺇ546 per night
Guest favorite

Condo in Tidenham

4.96 out of 5 average rating, 89 reviews

Annexe with stunning views over the River Severn

Apr 9 – 16

ﺩ.ﺇ339 per night
Guest favorite

Home in Tidenham Chase

4.94 out of 5 average rating, 16 reviews

The Dairy - Wye Valley Area of outstanding beauty

Aug 13 – 20

ﺩ.ﺇ304 per night
Guest favorite

Home in Bulwark

5.0 out of 5 average rating, 24 reviews

Modern, Newly Built, Two Double Bedroom House

Nov 26 – Dec 3

ﺩ.ﺇ484 per night
Guest favorite

Cottage in Chepstow

4.97 out of 5 average rating, 37 reviews

Charming 3BR Chepstow cottage w/parking & garden.

Jan 30 – Feb 6

ﺩ.ﺇ883 per night

Quick stats about vacation rentals in Chepstow

Total rentals

20 properties

Local attractions

Panevino Italian Restaurant, Lidl Chepstow, and Coffee#1 Chepstow

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

20 properties include access to wifi

Total number of reviews

1.4K reviews

Nightly prices starting at

ﺩ.ﺇ37 before taxes and fees

Destinations to explore

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