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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Top Guest favourite
Apartment in Monmouthshire
4.91 out of 5 average rating, 121 reviews

Cromwell House, Central Chepstow

Flat 1 is a cosy first floor flat in Cromwell House steeped in history and named after Oliver Cromwell having stayed here when invading the famous Chepstow Castle. We have recently refurbished the property to create a warm and welcoming place to enjoy all that Chepstow and the surrounding areas has to offer. This special place is close to everything and central to Chepstow making it easy to plan your visit. The flat is fully equipped with every thing you would need for your stay along with Wi-Fi

Guest favourite
A spacious garden showcases blooming flowers, including tulips and bluebells, framed by a stone wall. Lush greenery fills the background, featuring tall trees and scattered shrubs. A decorative stone feature stands centrally, surrounded by vibrant plant life under a clear blue sky.
Cottage in Tidenham Chase
4.89 out of 5 average rating, 149 reviews

Goldcrest-Lodge-Forest-of-Dean

Take it easy at this unique and tranquil getaway. Set in the Wye Valley, an area of outstanding natural beauty. You can walk/cycle for miles without touching a road. Collect eggs, milk and delicious ice cream from the farm next door Tintern Abbey with its pubs and restaurants is a walk away (an hour); the races, music at the Castle, Clearwell Caves, Puzzlewood, steam train.. and more. Travelling with friends/family? Check our other listing within the same grounds airbnb.com/h/wyevalleydairy-uk

Top Guest favourite
The exterior of Pineapple Cottage is shown, featuring a gray facade and a teal front door. Two potted plants sit beside the doorway. A cobbled street leads upward, lined with traditional buildings and a lantern light adding a touch of character to the scene.
Cottage in Chepstow
4.87 out of 5 average rating, 505 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.

Superhost
Hut in Sedbury
4.8 out of 5 average rating, 114 reviews

Offas Dyke Cabin Garden Cottage Sedbury NP167EY

Offas Dyke Cabin is set on a hill surrounded by organic countryside. The views of the Severn Estuary are spectacular, withThe Severn Bridge standing proud amongst it . . We are lucky to be located at the start or finnish of the historic Offas Dyke Path which offers beautiful walks and scenery. The cabin is walking distance to the local village pub which offers a hearty Sunday lunch. Chepstow Town centre with its quirky shops , restaurants and beautiful historical Castle are 5 minutes away .

Top Guest favourite
A row of colorful terraced houses is showcased, featuring distinct facades in shades of white, gray, green, and yellow. A bright pink door is prominent, complemented by a charming window with lace curtains. The scene captures the character of the street in Chepstow.
Townhouse in Chepstow
4.95 out of 5 average rating, 272 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.

Top Guest favourite
The historic Welsh Gatehouse features an imposing stone exterior with two prominent towers. Architectural details include ancient windows and a large, arched entrance. Surrounding greenery adds to the charm of this medieval structure, set against a clear blue sky.
Castle in Chepstow
4.94 out of 5 average rating, 188 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.

Top Guest favourite
A charming cottage emerges from a lush garden, framed by vibrant green foliage and blooming flowers. The warm wooden windows of the cottage are partially obscured by the surrounding greenery, creating a peaceful and inviting atmosphere in this natural setting.
Cottage in Saint Briavels
4.99 out of 5 average rating, 352 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.

Top Guest favourite
A bright lounge area features a green sofa adorned with patterned cushions. Nearby, a small drum set is positioned next to a vibrant red wall art piece. Natural light enters through the windows, and decorative elements add a creative touch to the space.
Guest suite in Southville
4.97 out of 5 average rating, 170 reviews

Your own space in colourful Southville!

Hello! Our home is in the vibrant and colourful area of Southville, just a short 15 minute walk from Bristol city centre. Southville is a very popular part of Bristol and home to Upfest, which is Europe’s biggest street art festival. The accommodation itself is a self-contained part of our home with its own private entrance. Inside, you’ll find a bright and spacious bedroom with en suite shower room. Directly beneath in the basement is a lounge area with kitchenette.

Superhost
A vibrant outdoor seating area features a circular table surrounded by four folding chairs. A striped umbrella provides shade, and a small potted plant sits at the center of the table. The green lawn enhances the inviting atmosphere.
Loft in Saint Briavels
4.75 out of 5 average rating, 220 reviews

Tuckers Lodge

We are situated less than a mile away from the village of St Briavels. We are fairly rural, so what 3 words is a great way to find us, they are: endlessly.balance.drummers Saint Briavels is a vibrant little village in the Forest of Dean, on the edge of the beautiful Wye Valley. It has an inn, a deli, a church and a castle. A monthly farmers' market is held in the village on the first Saturday morning of every month, where you can buy a whole range of local produce.

Top Guest favourite
A well-lit bedroom features a double bed with a simple, patterned duvet, flanked by two bedside tables with lamps. A comfortable black sofa is positioned nearby. Natural light enters through curtains that frame a window, enhancing the serene atmosphere of the space.
Guesthouse in Magor
4.95 out of 5 average rating, 491 reviews

Private Annex with gated parking close to M4.

Modern, light and homely annex on private land with gated parking situated in a lovely little village called Magor. The village shops, restaurants and pubs are a short five minute stroll away and are well worth a visit. Magor has fantastic links being 2 minutes from the M4. We are approx 30 minutes to centre of Bristol and 30 minutes to Cardiff, 20 minutes to centre of Newport and 10 minutes to the Celtic Manor Resort and ICC.

Top Guest favourite
Apartment in Saint Arvans
4.93 out of 5 average rating, 122 reviews

The Nursery Wing - Wyndcliffe Court

The Accommodation is just off the Wye Valley walk at Upper Wyndcliff, a spacious and comfortable self-contained first floor flat within a private family house and garden with fabulous views. Guests can explore the beautiful gardens - which they may have seen featured in the May 2022 edition of "The English Garden". There are also wonderful walks and cycle rides from the door to Tintern, Chepstow and the AONB of the Wye Valley.

Guest favourite
A bright kitchen area features wooden flooring and natural light from a window. A wooden dining table with four chairs is present, complemented by a potted plant in the corner. The kitchen is equipped with modern appliances and white cabinetry.
Cottage in Monmouthshire
4.89 out of 5 average rating, 471 reviews

Carpenters Cottage - Central Chepstow with parking

Carpenters Cottage is a quaint cosy one bedroom cottage at the bottom of Chepstow Town. It’s 2 minutes walk to the castle, town centre or the pubs on the river wye. The cottage is fully equipped with all your necessities for a wonderful home from home stay. Recently completely refurbished to a high standard it offers comfort, style and privacy with a 4* luxury finish. We hope you enjoy your stay and want to come again.

Popular amenities for Chepstow holiday rentals

When is the best time to visit Chepstow?

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Avg. price$206 NZD$209 NZD$214 NZD$219 NZD$223 NZD$228 NZD$243 NZD$246 NZD$243 NZD$228 NZD$221 NZD$241 NZD
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Frequently Asked Questions

  • Do house rentals in Chepstow have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Chepstow. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Chepstow?

    Chepstow has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Chepstow have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Chepstow. Enjoy a tailored experience with all the comforts you desire.

  • Where should I stay in Chepstow?

    Make yourself at home in Chepstow by choosing from our most frequently booked neighborhoods. We have over 70 vacation rentals in Chepstow, and over 70 vacation rentals in Pwllmeyric.

  • How much does it cost to stay in house rentals in Chepstow?

    Experience the best of Chepstow with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for House Rentals in Chepstow?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Chepstow

  • Total holiday rentals

    Explore 30 holiday rentals in Chepstow

  • Nightly prices starting at

    Chepstow holiday rentals start at $33 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,790 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Wi-Fi availability

    30 of Chepstow holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chepstow rentals

  • 4.9 Average rating

    Chepstow stays are highly rated by guests—averaging 4.9 out of 5!

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