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Holiday houses in Chepstow

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Top-rated holiday 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, 355 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.

2–9 Jan

$181 NZD per night

Guest favourite

Townhouse in Chepstow

4.95 out of 5 average rating, 164 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.

17–24 Feb

$182 NZD per night

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.

14–21 Sep

$190 NZD per night

Guest favourite

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.

28 Feb – 7 Mar

$377 NZD per night

Guest favourite

Cottage in Saint Briavels

4.99 out of 5 average rating, 292 reviews

Set in 40 Acres of Private Countryside in AONB

Nestled in rolling hills with 40 acres of private tracks, fields, streams, woodland and ancient lime kilns to explore, this rural hideaway is popular with walkers, cyclists and those just wishing to escape the mass media or hustle and bustle of everyday life. Recharge your batteries and enjoy the great outdoors as you toast some marshmallows over the fire pit, say hello to the pet sheep and soak up the sights and sounds of birds, wildlife and sunsets in this peaceful relaxing retreat.

3–10 Feb

$217 NZD per night

Guest favourite

Cottage in Brockweir

4.99 out of 5 average rating, 175 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

25 Sep – 2 Oct

$265 NZD per night

Guest favourite

Guest suite in Tockington

4.95 out of 5 average rating, 326 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.

24–31 Mar

$147 NZD per night

Guest favourite

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.

25 Mar – 1 Apr

$186 NZD per night

Guest favourite

Condo in Earlswood

5.0 out of 5 average rating, 158 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.

3–10 Sep

$175 NZD per night

Guest favourite

Apartment in Caldicot

4.95 out of 5 average rating, 329 reviews

Cosy apartment

This is a first floor apartment with a large main bedroom containing a large super king bed or 2 singles, a small room with a settee and TV, a kitchen and a shower room. There's a small hallway downstairs leading to a private terrace. We are close to Caldicot Castle, St Pierre, Celtic Manor Resort, Brooms Event Centre, Wye Valley, Wales Coastal Path and Offa's Dyke. Caldicot is a small town close to the M4 & M5 motorways so easy reach of many locations.

6–13 Sep

$142 NZD per night

Guest favourite

Cottage in Chepstow

4.9 out of 5 average rating, 103 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*

4–11 Nov

$338 NZD per night

Guest favourite

Cottage in Llandogo

4.92 out of 5 average rating, 171 reviews

Gorgeous Stone Cottage in the Lower Wye Valley

Mill Cottage is a delightful stone cottage situated on a private lane in the heart of a pretty village located on the River Wye. The original cottage is over 150 years old and was the home of the sawmill manager, who ran the nearby sawmill, which has long since disappeared. It is now a lovely holiday cottage, that sleeps two couples and one well-behaved dog. It overlooks a pretty church and is very conveniently located for the village pub.

30 Oct – 6 Nov

$222 NZD per night

Holiday rentals for every style

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Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Chepstow holiday rentals

Free parking on premises

Air conditioning

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 holiday rentals in Chepstow

Guest favourite

Hut in Chepstow

4.95 out of 5 average rating, 152 reviews

Chestnut Lodges - Luxury Glamping Pod Hazel Lodge

23–30 Dec

$249 NZD per night

Guest favourite

Cottage in Monmouthshire

5.0 out of 5 average rating, 26 reviews

Historic cottage opposite Chepstow Castle

6–13 Nov

$237 NZD per night

Apartment in Monmouthshire

4.85 out of 5 average rating, 13 reviews

Cromwell House, Central Chepstow

21–28 Dec

$220 NZD per night

Guest favourite

Guesthouse in Monmouthshire

4.92 out of 5 average rating, 12 reviews

Self-contained Annexe, Chepstow

16–23 Jun

$126 NZD per night

Guest favourite

Guesthouse in Monmouthshire

4.99 out of 5 average rating, 78 reviews

The coachouse.

1–8 Oct

$259 NZD per night

Guest favourite

Condo in Monmouthshire

5.0 out of 5 average rating, 47 reviews

Castle House Apartment 2 Georgian town house

27 Sep – 4 Oct

$254 NZD per night

Guest favourite

Condo in Tidenham

4.96 out of 5 average rating, 90 reviews

Annexe with stunning views over the River Severn

24 Apr – 1 May

$154 NZD per night

Guest favourite

Holiday home in Monmouthshire

4.94 out of 5 average rating, 63 reviews

Spacious Chepstow home with private garden & patio

9–16 Oct

$333 NZD per night

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
1.6K reviews
Nightly prices starting at
$17 NZD before taxes and fees

Destinations to explore