Holiday rentals in Chepstow

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chepstow

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

%{current} / %{total}1 / 1
Top guest favourite
A well-lit bedroom features a spacious metal-framed bed with a dark quilt and a decorative pillow. Two bedside tables with lamps flank the bed. Light grey curtains frame a window, while a full-length mirror is positioned against one wall, complementing the room's neutral tone.
Flat in Chepstow
4.91 out of 5 average rating, 122 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

Top guest favourite
A cozy living area is presented, featuring a blue sofa paired with a yellow armchair adorned with a decorative pillow. A coffee table sits in front, with a wood-burning stove on one side. Natural light filters through a multi-pane window, framed by dark curtains.
Cottage in Chepstow
4.87 out of 5 average rating, 508 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
An outdoor space features a wooden deck with a seating area. A cozy sofa adorned with colorful cushions complements a table and chairs. String lights are hung overhead, adding a charming touch to the cabin's entrance, which is framed by light blue doors.
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 modern A-frame house is framed by a vibrant garden featuring tall grass and clusters of purple flowers. Large glass windows provide a view into the warmly lit interior, showcasing a cozy ambiance. Surrounding trees create a natural backdrop to this inviting space.
Place to stay in Lympsham
5 out of 5 average rating, 210 reviews

Romantic Somerset hideaway

Hello! We are Rob and Kate and we have poured our heart and soul into our guest house. Tucked away on the outskirts of sleepy Lympsham, enjoy the countryside around you whilst resting your legs after walking the renowned mendips. Enjoy a glass of wine whilst watching the many birds in the surrounding trees or be a little more adventurous with the numerous local cycle routes. We look forward to meeting you on your stay. Shared driveway next to main house. Not suitable for children or pets.

Guest favourite
A charming stone cottage is set against a backdrop of lush greenery. The two-story structure features large windows, showcasing natural light. The surrounding area is accented by trees and plants, with a slight incline leading to the entrance.
Cottage in Monmouthshire
4.92 out of 5 average rating, 129 reviews

The Old Coach House at Tintern, the Wye Valley

The old coach House is a few minutes walk from the centre of Tintern on the banks of the river Wye, where you'll find the famous abbey, as well as places to eat and drink, and shops selling local crafts. The Wye Valley Walk passes the house, and the hourly bus between Chepstow and Monmouth stops just metres away. Staying at the historic Old Coach House in Tintern, you'll experience the unique charm of an early 1800s Welsh cottage, while enjoying modern comforts in a stylish and homely setting.

Top guest favourite
The sitting area features a comfortable sofa with accent pillows positioned around a decorative fireplace. A mirror above the fireplace reflects light, while a TV is mounted on the wall. Light wooden flooring creates a warm atmosphere, complemented by soft, neutral walls.
Townhouse in Chepstow
4.95 out of 5 average rating, 273 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 traditional cottage is partially obscured by lush greenery, featuring a white exterior and prominent chimneys. A conservatory is visible, and trees frame the surroundings, creating a tranquil and inviting setting in the heart of nature.
Home in Trelleck
5 out of 5 average rating, 103 reviews

Cute little Wye Valley cottage

Surrounded by woodland with hilltop views across the Wye Valley to Offa’s dyke, this eco friendly traditional Monmouthshire cottage is the perfect place to unwind and enjoy nature at its very best. Spend time in the garden listening to bird song and the gentle babbling of the stream or step out the gate to explore Cleddon Falls and beautiful view points along the Wye Valley walk. The medieval village of Trellech and Tintern Abbey are also within easy reach off or on road by foot, bike or car.

Top guest favourite
A quaint stone cottage is framed by lush greenery, featuring a large window that invites natural light inside. The well-maintained lawn includes neatly trimmed hedges and a comfortable seating area, creating a serene outdoor environment.
Cottage in Monmouthshire
4.97 out of 5 average rating, 191 reviews

Peaceful Stone Cottage among fabulous gardens

The Garden House is a peaceful stone cottage set in the historic gardens of High Glanau Manor, the home of H. Avray Tipping (1855-1933) the Architectural Editor of Country Life Magazine from 1907. High Glanau Manor is an important Arts & Crafts house set in 12 acres of gardens designed in 1922. The gardens retain many original features including formal terraces, octagonal pool, glasshouse, pergola and 100 ft long double herbaceous borders. There are spectacular views to the Brecon Beacons

Top guest favourite
The cottage is set amongst lush greenery, featuring a spacious lawn and a well-kept garden. Its exterior is painted white, with large windows and a welcoming entrance. A backdrop of trees adds to the tranquil atmosphere, creating a serene retreat in the countryside.
Cottage in Brockweir
4.99 out of 5 average rating, 261 reviews

3 bedroom, peaceful, secluded, & large garden

Hidden away on the edge of the ancient Forest of Dean, in the beautiful Wye Valley, with a large secluded garden, accessed by a mile long, narrow, single track lane, hanging with ferns in summer. It's is a fabulous place for walkers and town escapees. Once a woodman’s cottage, with a cosy, spacious interior, fully equipped kitchen, log burner, very comfortable beds, all you need for a relaxing break. Not suitable for young children 1-12, the large garden has a pond and steep terracing.

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 Mathern
4.94 out of 5 average rating, 189 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 Newland
4.99 out of 5 average rating, 353 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.

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 Chepstow
4.89 out of 5 average rating, 474 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?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price£92£94£96£98£100£102£109£110£109£102£99£108
Avg. temp4°C5°C7°C9°C12°C15°C17°C17°C14°C11°C7°C5°C

Frequently Asked Questions

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • Do house rentals in Chepstow have free parking?

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

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 £15 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 & child-friendly amenities

  • Wifi availability

    30 of Chepstow holiday rentals include wifi 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