Holiday Rentals in Chepstow

28 available vacation rental offers

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Chepstow holiday rentals
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28 Holiday Rentals and Airbnb in Chepstow

Best family friendly Chepstow holiday rentals

Among the 28 accommodations in Chepstow, here are the 4 best family friendly rentals

Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chepstow
Chepstow
24/07 – 27/07
NZ$864/nighttotal: NZ$2592 (3 )

Cottage ∙ 3 Bedrooms ∙ 6 Guests

3 5
cottage
This Vale of Usk cottage, situated 11km from shops and 1.6km from restaurants and pubs, offers stunning views and is close to Monmouth, Chepstow, and Ross-on-Wye.
The three-bedroom, three-bathroom dwelling sleeps six, features a fully equipped kitchen with dishwasher, private parking, and an enclosed courtyard with barbecue, ideal for families.
Bilsham Meadows - Chepstow
9.6 21 reviews
Chepstow
01/07 – 02/07
NZ$3422/nightfor 1 night

Bilsham Meadows

5 1
house , Bristol
This five-bedroom Bristol house, situated in Bilsham Meadows, is approximately 19 kilometres from Bristol Parkway Station and within easy reach of attractions including Bristol Cathedral and Ashton Court.
The 160 square metre property boasts three bathrooms with walk-in showers and hot tubs, a fully equipped kitchen, a swimming pool, a jacuzzi, a garden, and parking; golfing and cycling are nearby.
Cottage ∙ 3 Bedrooms ∙ 5 Guests - Chepstow
Chepstow
27/06 – 04/07
NZ$403/nighttotal: NZ$2821 (7 )

Cottage ∙ 3 Bedrooms ∙ 5 Guests

3 2
cottage , Hewelsfield
This pet-friendly barn conversion in Hewelsfield, Wye Valley and Forest of Dean, offers panoramic views and direct access to Offa's Dyke and the Wye Valley Walk, located 2.75 kilometers from the nearest restaurant and 1.6 kilometers from Tintern Abbey.
This luxury cottage sleeps five guests, featuring three bedrooms, two bathrooms with underfloor heating on the ground floor, a dishwasher, Wi-Fi, an enclosed garden with a BBQ, and is ideally situated for exploring nearby attractions like Chepstow Castle and the Forest of Dean.
Large Detached House In Almondsbury, North Bristol - Chepstow
9.9 35 reviews
Chepstow
27/06 – 04/07
NZ$1720/nighttotal: NZ$12040 (7 )

Large Detached House In Almondsbury, North Bristol

4 2
apartment , Almondsbury
This four-bedroom house in North Bristol is just a short drive from the Cotswolds and the Wave surfing park, offering easy access to Bristol and the M4/M5 interchange. The property has received excellent ratings for location, cleanliness, and user experience, making it a great choice for families and groups.
The house has a spacious open-plan kitchen diner, a separate snug with a real fire, and a dedicated office space, comfortably accommodating up to seven guests. Amenities include a modern kitchen with a dishwasher and washing machine, a family bathroom, a garden, and off-street parking for two cars.

Best Chepstow holiday rentals with parking

4 Bed Luxury Home, Sauna, Hot Tub, Sleeps 9 - Chepstow
10 1 review
Chepstow
24/07 – 27/07
NZ$1407/nighttotal: NZ$4221 (3 )

4 Bed Luxury Home, Sauna, Hot Tub, Sleeps 9

1 5
house , Chepstow
This Chepstow dwelling is situated 21 kilometres from Bristol Parkway Station and within 29 kilometres of Bristol's Cabot Circus and Clifton.
This 30 square metre holiday home offers accommodation for 9 guests, featuring a kitchen with a dishwasher and oven, a private sauna, a hot tub, and a terrace with garden views.
Beautiful 1-bed Cottage In Trellech - Chepstow
9.2 140 reviews
Chepstow
29/08 – 30/08
NZ$254/nightfor 1 night

Beautiful 1-bed Cottage In Trellech

1 2
house , Trelleck
This charming cottage is located in the picturesque village of Trellech, just 23 miles from Bristol Parkway Station and 27 miles from Cabot Circus in Bristol, offering a peaceful escape from the city. It has received excellent ratings for location, cleanliness, and overall user experience.
The cottage has one bedroom and one bathroom, offering comfortable accommodation for up to two guests. It features a private patio, free parking, free Wi-Fi, and a comfortable living space, perfect for a relaxing getaway in the Welsh countryside.
Luxury 4 House,hot Tub,sleeps 9,wi-fi - Chepstow
10 1 review
Chepstow
13/08 – 16/08
NZ$1407/nighttotal: NZ$4221 (3 )

Luxury 4 House,hot Tub,sleeps 9,wi-fi

1 4
house , Chepstow
This Chepstow holiday home is located 20.9 kilometres from Bristol Parkway Station and 27.4 kilometres from Cabot Circus, offering convenient access to city amenities.
This 30 square meter cottage provides accommodation for up to 9 guests in a 1-bedroom layout, featuring a kitchen with a fridge, microwave oven, and dishwasher, a Jacuzzi, terrace, garden, and parking.
Modern Three Bedroom House Free Parking Wifi - Chepstow
9.6 12 reviews
Chepstow
29/08 – 30/08
NZ$457/nightfor 1 night

Modern Three Bedroom House Free Parking Wifi

3 2
house , Bristol
This 2-bedroom property in Bristol is situated 3.2 kilometres from Bristol Parkway Station, 12.2 kilometres from Clifton, and 12.4 kilometres from Bristol Temple Meads Station.
This detached house offers parking, WiFi, and a kitchen equipped with a fridge and microwave, accommodating up to 9 guests with 3 bathrooms and a 10:00 AM check-out.

Frequently asked questions about holiday rentals in Chepstow

  • What are some interesting places to visit in or near Chepstow?

    Chepstow Castle is a must-see, it's a Norman castle with a rich history. If you want something a bit different, the Wye Valley is just a short drive away, and it's a beautiful area with lots of walking trails and stunning views. And for something a bit more modern, the Chepstow Racecourse is a great place to catch a horse race.
  • What are the best Airbnb and holiday rentals in Chepstow?

    Broadrock Accommodation - Clock Cottage, Chepstow Town - Welsh Cottage and Sedbury Farm Cottages #2 are among the best Airbnb and holiday rentals in Chepstow.

  • Which walking or cycling routes are the best in Chepstow?

    The Offa's Dyke Path runs right through Chepstow, it's a long-distance trail that follows the border between England and Wales, and there are some great shorter walks you can do right in town. If you're into cycling, the Wye Valley Cycle Path is a great option. It's a traffic-free route that follows the River Wye.
  • What are the most popular Airbnbs in Chepstow?

    Among the Airbnbs in Chepstow, Chepstow Town - Welsh Cottage, Sedbury Farm Cottages #2 and Peaceful - Rural Apartment With River Views are the most popular ones.

  • What sports or outdoor activites can visitors enjoy in and around Chepstow?

    Chepstow is a great place for outdoor activities. You can go kayaking or canoeing on the River Wye, or go for a hike in the Wye Valley. There's also a great golf course at Chepstow Golf Club, and the Chepstow Racecourse hosts horse racing events throughout the year.
  • What are the best holiday rentals with a pool in Chepstow?

  • What other towns or cities can be easily accessed from Chepstow?

    Chepstow is well-connected, you can easily get to Bristol, Newport, and Cardiff by car or train. If you're looking for a day trip, Tintern Abbey is a beautiful historic site just a short drive away.
  • What are the best rentals for families and kids in Chepstow?

    The best rentals for families and kids in Chepstow are Broadrock Accommodation - Clock Cottage, Chepstow Town - Welsh Cottage and Sedbury Farm Cottages #2.

  • What amenities are commonly available in vacation rentals in Chepstow?

    Most vacation rentals in Chepstow will have the basics like a kitchen, bathroom, and bedrooms. But you can also find places with extras like a garden, a patio, or even a hot tub. Many rentals also offer Wi-Fi and parking.
  • What are the best rentals or Airbnbs with a jacuzzi in Chepstow?

    The best holiday rentals or Airbnb with a jacuzzi in Chepstow are 5 Bed Luxury House With Swimming Pool, 5br Luxury House With Swimming Pool Chepstow Town and Court Park Barn.

  • What time of year is best to rent a vacation rental Chepstow?

    The best time to visit Chepstow really depends on what you're looking for. If you want to enjoy the warm weather and outdoor activities, then summer is a great time to visit. But if you want to avoid the crowds and enjoy the beautiful autumn colours, then late September or October is a good option.

Destinations nearby

Best Chepstow holiday rentals with a balcony

Olli's Cottage-terrace & Jacuzzi Optional - Chepstow
9.7 99 reviews
Chepstow
29/08 – 30/08
NZ$436/nightfor 1 night

Olli's Cottage-terrace & Jacuzzi Optional

1 2
house , Bristol
Olli's Cottage is conveniently located in Bristol, just a short distance from Bristol Parkway Station and Bristol Zoo. The property enjoys excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The cottage offers a comfortable and modern stay for two guests, with one bedroom and one bathroom in a 70 square metre space. The property boasts a private patio, free parking, a well-equipped kitchen, a walk-in shower, a flat-screen TV, and a swimming pool and jacuzzi for ultimate relaxation.
Baker's Bun - Sleeps 7 - Spacious Home - Parking & Garden - Bradley Stoke Bristol - Chepstow
Chepstow
08/08 – 10/08
NZ$796/nighttotal: NZ$1592 (2 )

Baker's Bun - Sleeps 7 - Spacious Home - Parking & Garden - Bradley Stoke Bristol

4 7
house , Bristol
This spacious 4-bedroom property is situated in Bradley Stoke, Bristol, 2.6 kilometres from Bristol Parkway Station and within 12.7 kilometres of Bristol Temple Meads Station and Cabot Circus.
This detached house offers accommodation for up to 7 guests, featuring a well-equipped kitchen with a dishwasher, a private garden with seating, a balcony, free private parking, and is close to cycling routes.
The Nook - Chepstow
10 1 review
Chepstow
27/06 – 04/07
NZ$459/nighttotal: NZ$3213 (7 )

The Nook

1 2
house , Tidenham
The Nook in Tidenham offers a peaceful countryside escape, situated approximately 27 kilometres from Bristol Parkway station and within easy reach of Bristol's attractions including Bristol Cathedral and Cabot Circus.
This self-catering cottage boasts a 10 square metre floor area, sleeping two guests in one bedroom with one bathroom, a private hot tub, and free Wi-Fi and parking.
2 Bed Barn, Open Living Space , Pet Friendly, Rural, With Easy Access From M4 - Chepstow
10 3 reviews
Chepstow
24/07 – 27/07
NZ$470/nighttotal: NZ$1410 (3 )

2 Bed Barn, Open Living Space , Pet Friendly, Rural, With Easy Access From M4

2 5
apartment , Usk Monmouthshire
This Monmouthshire holiday home is situated in a peaceful rural setting, within 14.5km of Usk Castle and the Wye Valley, offering easy access to other historic castles including Llangibby Motte and Castle, Caerleon Castle, and Raglan Castle.
The 120 square metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, private balcony, fireplace, free WiFi, and ample parking.

Best pet friendly Chepstow holiday rentals

Among the 28 accommodations in Chepstow, here are the 4 best pet friendly rentals

Gardeners Cottage At Mathern Palace - Chepstow - Chepstow
10 2 reviews
Chepstow
13/08 – 16/08
NZ$406/nighttotal: NZ$1218 (3 )

Gardeners Cottage At Mathern Palace - Chepstow

2 4
cottage , Chepstow
This Chepstow holiday home is situated 1.3km from St Pierre Country Club, 3km from Chepstow Castle, and 5km from Chepstow Racecourse, offering easy access to local attractions.
Sleeping four guests in two bedrooms and one bathroom, the self-catering property includes a fully equipped kitchen with fridge, microwave, oven and washing machine, plus a Smart TV and peaceful garden with parking.
The Snug, Pet Friendly, With A Garden In Caerwent - Chepstow
10 1 review
Chepstow
29/08 – 30/08
NZ$697/nightfor 1 night

The Snug, Pet Friendly, With A Garden In Caerwent

1 2
cottage , Chepstow
The Snug is a single-storey cottage located in Llanvair Discoed, a village near Caerwent, about 8km west of Chepstow. It's a peaceful escape in a quiet village setting, close to several attractions.
The cottage has a studio-style living space with a king-size bed, a sofa bed, and a fully equipped kitchen, making it ideal for a couple or a small family. It provides amenities such as WiFi, off-road parking, a side patio, electric heating, and a pub within walking distance.
The Potting Shed At Mathern Palace - Chepstow
10 37 reviews
Chepstow
13/08 – 16/08
NZ$547/nighttotal: NZ$1641 (3 )

The Potting Shed At Mathern Palace

1 4
apartment , Mathern
The Potting Shed is a beautifully restored 19th-century hay barn located on the historic grounds of Mathern Palace, just a short walk from the village pub and within easy reach of Bristol. The cottage has received excellent user ratings for its location, cleanliness, and overall experience.
The Potting Shed is a comfortable cottage with two bedrooms and one bathroom, sleeping up to four guests. It features a modern open-plan kitchen/diner, a separate lounge, a generous gravel front garden, and access to a shared large garden, perfect for relaxing and enjoying the peaceful Welsh countryside.
The Elements Residence - Chepstow
Chepstow
13/08 – 16/08
NZ$2090/nighttotal: NZ$6270 (3 )

The Elements Residence

10 4
apartment , Chepstow
This luxury residence in Chepstow offers a secluded setting within a walled garden, located just 500 meters from the town centre and Chepstow railway station, with Chepstow Castle and riverside walks also within easy reach.
This versatile property, ideal for groups, accommodates up to 26 guests across 10 bedrooms and 8 bathrooms, featuring a large kitchen, spacious living areas, and private parking for 4 vehicles, with additional free parking available.
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