Villas and Holiday homes in Chepstow

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Chepstow holiday homes
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25 Villa rentals in Chepstow

Find Holiday Homes in the City Centre of Chepstow

Stay near top-rated restaurants and major sights with central holiday homes in Chepstow city centre.

Chepstow Town. Welsh Cottage. - Chepstow
9.9 302 reviews

Chepstow Town. Welsh Cottage.

house
This charming house is located in the centre of Chepstow, just a short walk from the castle, Priory Church, and the River Wye. It has received excellent ratings for its location, cleanliness, and overall user experience.
The house is ideal for families, with two bedrooms and a guest capacity of four. It offers a spacious living area, a fully equipped kitchen, and a private garden, perfect for enjoying the beautiful surroundings.
Self-contained Annexe, Chepstow - Chepstow
9.8 64 reviews

Self-contained Annexe, Chepstow

house
This private annexe is located in central Chepstow, just 700 metres from the town centre and close to the racecourse, the Wye Valley, the River Wye, and Chepstow Castle. The property has received excellent ratings for its location, cleanliness, and overall experience.
The annexe is a modern and refurbished one-bedroom self-catering accommodation with an ensuite shower room, sleeping up to two guests. It offers essential amenities like a small fridge, tea and coffee making facilities, a DAB radio, and Wi-Fi access via a personal hotspot. Free on-street parking is available within a 3-minute walk.
Richmond House Apt 2 - Chepstow
9.1 15 reviews

Richmond House Apt 2

house, Chepstow
Apartment 2, a Chepstow holiday home, is conveniently located 22.5km from Bristol Parkway Station and 27.4km from Cabot Circus, offering easy access to both Bristol and Chepstow's historic town centre.
This self-catering property boasts a 20 square metre floor area with one bedroom, one bathroom, and sleeps three guests, featuring a fully equipped kitchen, free Wi-Fi, free parking, and a flat-screen TV.
Number 10 - Chepstow
8.8 67 reviews

Number 10

house, Chepstow
This 3-bedroom house in Chepstow is conveniently located just 17 miles from Bristol Zoo and 18 miles from Bristol Temple Meads Station, making it a great base for exploring both the beautiful Welsh countryside and the bustling city of Bristol. Guests consistently rate the property as excellent for its cleanliness, location and overall experience.
The house can comfortably accommodate up to six guests and comes equipped with a fully equipped kitchen, a relaxing garden, and free private parking. Enjoy the modern amenities, including free Wi-Fi, a flat-screen TV and a washing machine, and take advantage of the house's proximity to Chepstow's historic castle, the River Wye, and the town's charming shops and restaurants.

Best family friendly Chepstow villas and holiday home

Among the 25 accommodations in Chepstow, here are the 4 best family friendly villas and holiday homes

La Villa Olli -Natural Pool & Jacuzzi - Chepstow
9.9 75 reviews

La Villa Olli -Natural Pool & Jacuzzi

house, Bristol
La Villa Olli is a spacious house in Bristol, situated close to the city's attractions, making it an ideal base for exploring. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This four-bedroom property comfortably accommodates up to eight guests. The house offers a range of amenities and activities for a relaxing and enjoyable stay, including a swimming pool, a jacuzzi, a garden, a bar, a tennis court, and a games room with a pool table and ping-pong table.
40 M² House ∙ 1 Bedroom ∙ 1 Guest - Chepstow
No reviews

40 M² House ∙ 1 Bedroom ∙ 1 Guest

house
This detached property is located in Devauden, Great Britain, offering a peaceful retreat with straightforward access to regional attractions.
This 40 square meter cottage provides one bedroom and one bathroom, equipped with a fridge, microwave, hob, oven, kettle, and freezer, along with internet access, parking, and complimentary linen and towels.
Medieval Manor For Group Stays! - Chepstow
9.9 107 reviews

Medieval Manor For Group Stays!

castle
The Medieval Manor is located in the historic village of Caldicot, just 200 metres from the local castle pub, offering a convenient base for exploring the area. This charming manor has consistently received excellent ratings for its cleanliness, location, and overall guest experience.
The manor provides spacious accommodation for up to 12 guests, with five bedrooms, additional sofa beds and mattresses, and exclusive access to the first and second floors. Guests can enjoy a range of amenities, including a fully equipped kitchen, a garden, air conditioning, and parking, as well as the option to arrange catering and entertainment services.
House ∙ 1 Bedroom ∙ 2 Guests - Chepstow
10 3 reviews

House ∙ 1 Bedroom ∙ 2 Guests

house, Saint Briavels
This single-storey holiday home is located near St Briavels, Gloucestershire, 8.8km from Lydney and the River Severn, and 15.3km from Monmouth, offering easy access to Tintern Abbey (9.7km), Ragland Castle (28.2km), Goodrich Castle (19.3km), and Symonds Yat (21km).
The 45 square metre self-catering property features one bedroom sleeping two, a super-king size bed, a shower room, an open-plan lounge/kitchen/diner with a partly vaulted ceiling, private parking for two cars, Wi-Fi, and stunning Wye Valley views from a private deck; optional private yoga classes can be arranged with the owner.

Frequently asked questions about villa rentals in Chepstow

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Best Chepstow villas and holiday homes with a garden

The Potting Shed At Mathern Palace - Chepstow
9.0 2 reviews

The Potting Shed At Mathern Palace

cottage, Mathern
The Potting Shed is a restored 19th-century barn located on the grounds of Mathern Palace, a Grade I listed building dating back to 1408, just a short walk from the village of Mathern and its pub, The Millers Arms. The surrounding area offers picturesque countryside walks and is within easy reach of Caerwent Roman Town and Thornbury Castle.
This charming cottage has two bedrooms and can accommodate up to four guests. It features a spacious open-plan kitchen/diner, a separate lounge, a gravel front garden and a shared back garden, plus a Smart TV with Netflix and Prime Video apps, and a welcome pack with local recommendations.
Well Cottage By Cliftonvalley Apartments - Chepstow
9.7 3 reviews

Well Cottage By Cliftonvalley Apartments

house, Bristol
Well Cottage, near Clifton Valley, Bristol, offers spacious family accommodation 4.8km from Bristol Parkway Station and within a 16-20km radius of Cabot Circus and Bristol Cathedral.
This four-bedroom property boasts 75 square metres of floor space, sleeping up to 17 guests, and includes a fully equipped kitchen with dishwasher, private garden, parking, and free Wi-Fi.
Gorgeous 3 Bed House In Bristol - Chepstow
6.5 17 reviews

Gorgeous 3 Bed House In Bristol

house, Bristol
This three-bedroom house near Bristol Parkway station (3km), offers convenient access to Bristol city centre (11-13km) and Bristol Airport (31km).
The 10-square-metre property features a full kitchen, private parking, Wi-Fi, and accommodates up to 11 guests, with a garden and terrace adding to its appeal.
Spacious Detached House With Garden & Parking - Chepstow
No reviews

Spacious Detached House With Garden & Parking

house, Bristol
This five-bedroom detached property is located in Bristol, 2.6 kilometres from Bristol Parkway Station and within a 24 kilometre radius of Bristol Airport, offering convenient access to Clifton, Cabot Circus, Bristol Temple Meads, and Bristol Cathedral.
This spacious house provides accommodation for up to 15 guests with 3 bathrooms, a kitchen equipped with a fridge and microwave, a jacuzzi, a terrace, garden, and on-site parking, with room service and a concierge service available.

Best Chepstow villas and holiday homes with parking

Oak Tree Cottage, Countryside Retreat With River View - Chepstow
9.1 51 reviews

Oak Tree Cottage, Countryside Retreat With River View

house, Lydney
Oak Tree Cottage is situated in Lydney, Gloucestershire, just 31 kilometres from Bristol Parkway Station and 37 kilometres from Cabot Circus, offering a peaceful escape close to the River Severn.
This two-bedroom house, with a spacious 108 square metres of floor area, is ideal for families, with a fully equipped kitchen, garden, and patio, perfect for enjoying the outdoors.
The Honey Pot - Chepstow
9.9 34 reviews

The Honey Pot

house, Chepstow
The Honey Pot is a charming holiday home located in Chepstow, just 21 miles from Bristol Zoo and 22 miles from Bristol Temple Meads Station, making it a great base for exploring both the town and the surrounding countryside. Guests have consistently rated the property highly for its cleanliness, location, and overall experience.
The house has one bedroom and one bathroom, offering comfortable accommodation for up to two guests. It boasts a fully equipped kitchen, a private garden with a hot tub, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
Spacious Shepherds Hut In The Wye Valley - Chepstow
9.9 52 reviews

Spacious Shepherds Hut In The Wye Valley

cabin
The Shepherd's Delight is a charming shepherd's hut located in the tranquil Wye Valley, just two minutes from the Wye Valley Walk and a short drive from the Forest of Dean. This well-rated accommodation has received excellent reviews for its location, cleanliness, and overall experience.
The hut is perfect for a couple looking for a peaceful retreat, with one bedroom and one bathroom. It comes equipped with modern amenities, including a kitchen with a fridge and freezer, a private outdoor seating area with a fire pit and BBQ grill, and free Wi-Fi.
The Potting Shed At Mathern Palace - Chepstow
9.8 43 reviews

The Potting Shed At Mathern Palace

house, Chepstow
The Potting Shed is a charming holiday home located just 22 kilometres from Bristol Parkway Station and 29 kilometres from Bristol Zoo, offering a tranquil retreat in the heart of Chepstow. The property has received excellent ratings for its location, cleanliness and overall experience.
The cottage has two bedrooms and one bathroom, comfortably accommodating up to four guests. Guests can enjoy a well-equipped kitchen with a dishwasher, a private garden, and free parking and Wi-Fi.

Compare Holiday Homes with a Pool in Chepstow

A holiday home in Chepstow with a swimming pool makes enjoying a proper swim in the heart of the city remarkably convenient.

Cottage ∙ 4 Bedrooms ∙ 10 Guests - Chepstow
10 4 reviews

Cottage ∙ 4 Bedrooms ∙ 10 Guests

cottage, Pilning
The Old Rectory - Chepstow
9.7 3 reviews

The Old Rectory

house, Bristol

Find the Best Luxury Holiday Homes in Chepstow

A city-centre luxury holiday home in Chepstow guarantees a premium experience, offering 5-star comfort.

The Piggery - Chepstow
9.4 7 reviews

The Piggery

house, Woolaston

Browse Holiday Homes with a Hot Tub in Chepstow

Whether you prefer a jacuzzi or a hot tub, these holiday homes in Chepstow feature private facilities for a soak after a busy day.

The Honey Pot, Romantic, With Hot Tub In Chepstow - Chepstow
No reviews

The Honey Pot, Romantic, With Hot Tub In Chepstow

cottage, Chepstow
The Nook - Farm Stay With Hot Tub - Chepstow - Chepstow
10 8 reviews

The Nook - Farm Stay With Hot Tub - Chepstow

cabin, Chepstow
Willow Lodge - Chepstow
9.9 72 reviews

Willow Lodge

cabin
The Nook - Chepstow
10 1 review

The Nook

house, Tidenham
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