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Vacation rentals in Caldicot

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Top-rated vacation rentals in Caldicot

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

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Top guest favorite
Apartment in Portishead
4.99 out of 5 average rating, 282 reviews

Ground Floor, 2-bed Marina Apartment

A beautiful ground-floor apartment set right on the water’s edge of the idyllic Portishead Marina — a perfect retreat for families, friends, or couples seeking a quality escape. Ideally located, you’re just a 2-minute stroll from a delicious local bakery, cosy cafés, excellent restaurants, and a convenient mini supermarket. With scenic walking routes right on your doorstep — including the marina, coastal path, lake grounds, and nearby nature reserve. A relaxing and well located base to stay.

Guest favorite
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, 483 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.

Top guest favorite
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, 260 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 favorite
A cozy sleeping area features a spacious bed with white bedding and patterned pillows. A plaid throw drapes over the side. Light fills the room through two open windows, revealing expansive views of the lush countryside and rolling hills beyond.
Shepherd’s hut in Usk
4.98 out of 5 average rating, 165 reviews

Bespoke/Shower/L-burn/Wc/Stars/Dog/WiFi

Our hand built bespoke huts offer a luxurious and spacious living space to relax. Quality fixtures and fittings feature throughout. Located in beautiful countryside, stunning views and its amazing wildlife can be appreciated in the daytime and star gazing at night. An internal bathroom with double size power shower will ensure a luxurious experience. Its character wood stove will keep you cosy all year round. Luxury items: Handmade kitchen, Dab/Bluetooth radio, DVD / TV and Nespresso machine.

Guest favorite
A spacious lodge interior features a comfortable double bed with a premium mattress, set against a backdrop of artistic wall decor. Large glass doors provide natural light and lead to a garden area, while a wall-mounted smart TV and a kitchenette are visible in the background.
Home in Patchway
4.94 out of 5 average rating, 641 reviews

BEAUTIFUL Tiny House: Whitsun Lodge

Tiny little lodge/House in Bristol. Detached from our house with access to the garden. 10 minutes drive from THE WAVE. 30 seconds walk from Aerospace Bristol (Concorde museum) Great links to the City Centre Comprising of full kitchen, En-suite bathroom and shower, comfy double bed (premium mattress) Smart TV already connected to Netflix/NowTV/Disney+ Use of the washing machine if you need Me, My wife Charlee, My baby son Finley and our little Dog Louie look forward to welcoming you 😄

Superhost
The exterior of the Garden Cottage features a charming stone wall, a sloped roof with red tiles, and a wooden door painted in a soft grey. A small window allows natural light into the space, surrounded by lush greenery and a well-kept garden area.
Guest suite in Magor
4.84 out of 5 average rating, 157 reviews

Charming Welsh cottage with pretty garden.

Garden Cottage is a lovely contemporary addition to an 18th century Welsh long house. With separate access & pretty private garden area, it consists of a double bedroom with ensuite shower, spacious open plan kitchen/living room & separate utility area with washing machine. Additionally, there is an outside table and chairs for alfresco dining. Free wifi and gas central heating ensures guests' comfort and convenience. The property is not suitable for small children, as there is a deep pond.

Guest favorite
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
4.93 out of 5 average rating, 184 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 favorite
A feature arched window frames panoramic views of rolling hills and fields, with sunlight illuminating the stone wall and wooden shutters. A vase of fresh flowers sits on a round table, enhancing the inviting atmosphere of the open living space.
Cottage in Saint Briavels
5 out of 5 average rating, 334 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.

Guest favorite
An open-plan living area features a cozy gray sofa, a small TV mounted on the wall, and a dining table. Shelves display books and decorative items. Large windows allow natural light to fill the space, with a view of the outdoor landscape. A staircase with wooden steps leads to the mezzanine.
Guest suite in Tockington
4.96 out of 5 average rating, 418 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.

Top guest favorite
The living space features a combination of natural wood finishes and modern decor. A cozy seating area with a blue sofa complements a light wood dining table and chair. Sliding wooden doors separate the sleeping area, where a spacious bed is visible in the background.
Bungalow in Caldicot
4.98 out of 5 average rating, 225 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.

Top guest favorite
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
4.94 out of 5 average rating, 466 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.

Guest favorite
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, 462 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 Caldicot vacation rentals

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