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Vacation rentals in Chepstow

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Top-rated vacation rentals in Chepstow

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Cottage in Chepstow

4.84 out of 5 average rating, 357 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.

Jan 17 – 24

R1,955 ZAR per night

Townhouse in Chepstow

4.95 out of 5 average rating, 165 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.

Jan 13 – 20

R1,966 ZAR per night

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 23 – 30

R1,674 ZAR per night

Castle in Chepstow

4.93 out of 5 average rating, 150 reviews

Welsh Gatehouse: Luxury 13th Century Medieval Home

The Welsh Gatehouse is a beautiful historic house with modern amenities. Imagine staying in a fairy tale castle built in 1270. The thick walls, ancient windows & steep spiral staircase say 'history'. Romantic log fires keep you warm you in winter, & the thick walls keep you cool in summer. Views from the top of the tower are extraordinary over the Severn Bridges and the Breacon Beacons (NB we call this the terrace in our description below). Unique, luxurious, quirky yet comfortable.

Apr 11 – 18

R3,935 ZAR per night

Cottage in Saint Briavels

5.0 out of 5 average rating, 241 reviews

Set in AONB & 40 Acres of Private Countryside

Perfectly situated to explore all the Wye Valley and Forest of Dean has to offer, The Apple Loft is an idyllic getaway popular with honeymooners, walkers, cyclists and those just wishing to escape the hustle and bustle of everyday life. With panoramic views across Mork Valley, guests can walk our grassy tracks, explore the old lime kilns, picnic in our fields, say ‘hello’ to the pet sheep and enjoy the sights and sounds of nature, stars and sunsets in this magical and relaxing retreat.

Apr 14 – 21

R3,363 ZAR per night

Guest suite in Tockington

4.95 out of 5 average rating, 329 reviews

The Dairy - Quaint village stay

The Dairy is a quaint self-contained annex at the side of our detached property in the picturesque village of Tockington just north of Bristol. There is a bedroom on a mezzanine over an open plan living/dining/kitchen area and shower room. The accommodation is situation on the approach to the village, accessed from a private driveway with parking at the front. You have the use of a private veranda with views of the countryside and the opportunity to take in the village atmosphere.

Dec 24 – 31

R1,664 ZAR per night

Cottage in Brockweir

4.99 out of 5 average rating, 176 reviews

Peaceful, 3 bedroom woodland cottage, large space

Hidden away on the edge of the ancient Forest of Dean, in the beautiful Wye Valley. Set in a large secluded garden, accessed by a long narrow lane. It is a fabulous place for walkers and romantic escapees. Originally a woodman’s cottage, with a cosy-but-spacious interior, fully equipped kitchen, log burner, lovely, comfortable king sized beds, everything you need for a relaxing break. The large cottage garden is not suitable for young children 1-12, it has a pond and steep terracing

Nov 2 – 9

R2,956 ZAR per night

Cottage in Trelleck

4.96 out of 5 average rating, 185 reviews

The Old Cider Mill

The Old Cider Mill is a beautifully converted old cider barn set in the wonderfully peaceful monmouthshire countryside. The cottage is a fabulous romantic and tranquil retreat set in one acre of meadow and adjoining spinney. Perfectly situated to explore all the wye valley, and nearby forest of dean, has to offer. This cosy cottage sleeps two guests and has an open plan living area with a woodburning stove. Outside is lovely gravelled courtyard with furniture and off road parking.

Oct 18 – 25

R2,606 ZAR per night

Bungalow in Caldicot

4.98 out of 5 average rating, 172 reviews

Yeomans Lodge - Chepstow, Newly renovated.

Located within the grounds of the owners house, Yeomans Lodge is a newly renovated, quirky, self-contained, compact bungalow. It is a perfect location if you’re looking to escape to the countryside. The historic town of Chepstow and magnificent Wye Valley is a short drive away. Please note that the airbnb is in Crick, Chepstow, on some occasions the airbnb g00gle link takes you to Yeomans Acre in Gloucester which is the wrong location. Trying to sort the issue with Airbnb.

Jan 3 – 10

R2,025 ZAR per night

Condo in Earlswood

5.0 out of 5 average rating, 160 reviews

Luxurious homely and cosy 1st floor apartment.

The Folly first floor apartment is part of a contemporary country house set in four acres of gardens and paddocks. Whilst being part of the main house it is self-contained, fully furnished to a high standard and private. Open plan with dual aspect, lovely views to front and rear with balcony and seating overlooking the garden. King size and single bedrooms with immaculate shower room. Perfect rural location to escape to the country to re-charge and relax.

Sep 18 – 25

R1,907 ZAR per night

Cottage in Chepstow

4.9 out of 5 average rating, 104 reviews

Chepstow, Forest of Dean | Sleeps 4 | Dog Friendly

This warm and cosy cottage is based on the edge of the quiet village of Tutshill (the childhood home of JK Rowling) on the English side of the Welsh border. It is the perfect location if you are looking to escape to the country and explore the beautiful Forest of Dean but still be close to amenities. Walking distance to Chepstow. *10% discount for +7 night stays* *To book 12 months ahead or more please use the Airbnb website rather than the app*

Mar 10 – 17

R3,635 ZAR per night

Apartment in Gloucestershire

5.0 out of 5 average rating, 108 reviews

Idyllic Country Retreat in the Forest of Dean

Set in the grounds of a magnificent country home with far reaching stunning views over the River Severn and beyond. This is a perfect place to escape and unwind from the daily hustle and bustle of life. Near to Chepstow and with easy access to the M4 & M5 Motorways and only 2 hours drive from London, 30 minutes from Bristol and 40 minutes from Cheltenham. This cosy studio apartment has only recently been completed to an exceptionally high standard.

Oct 23 – 30

R2,032 ZAR per night

Vacation rentals for every style

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Cottages

Quaint homes, peaceful surroundings

Hotels

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Unique stays

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Popular amenities for Chepstow vacation rentals

Free parking on premises

Air conditioning

Stay near Chepstow's top sights

Panevino Italian Restaurant18 locals recommend

Coffee#1 Chepstow3 locals recommend

The Three Tuns6 locals recommend

Lime Tree5 locals recommend

M&S Chepstow Foodhall6 locals recommend

Stone Rock Pizza15 locals recommend

Other great vacation rentals in Chepstow

Cottage in Llandogo

4.93 out of 5 average rating, 174 reviews

Gorgeous Stone Cottage in the Lower Wye Valley

Mar 19 – 26

R2,344 ZAR per night

Guesthouse in Magor

4.95 out of 5 average rating, 360 reviews

Private Annex with gated parking close to M4.

Jan 30 – Feb 6

R1,436 ZAR per night

Hut in Chepstow

4.95 out of 5 average rating, 154 reviews

Chestnut Lodges - Luxury Glamping Pod Hazel Lodge

Jan 10 – 17

R2,770 ZAR per night

Cottage in Gwehelog

4.96 out of 5 average rating, 134 reviews

Cosy Stable @ Oak Farm

Sep 12 – 19

R1,745 ZAR per night

Cottage in Monmouthshire

4.98 out of 5 average rating, 126 reviews

Peaceful Stone Cottage among fabulous gardens

Jul 24 – 31

R3,025 ZAR per night

Bungalow in Chepstow

4.87 out of 5 average rating, 101 reviews

Pet friendly barn with views and green credentials

Apr 15 – 22

R2,143 ZAR per night

Condo in Thornbury

4.99 out of 5 average rating, 322 reviews

Delightful, comfortable, warm home away from home

May 25 – Jun 1

R1,619 ZAR per night

Home in Llanvaches

4.99 out of 5 average rating, 173 reviews

The Sheiling, stylish bungalow in quiet village

Jul 19 – 26

R3,110 ZAR 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
1.6K reviews
Nightly prices starting at
R188 ZAR before taxes and fees

Destinations to explore