Holiday Rentals in Chepstow

28 available vacation rental offers

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Chepstow holiday rentals
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Best Holiday rentals and Airbnb offers in Chepstow

Best family friendly Chepstow holiday rentals

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

3 Bedroom Accommodation In Devauden, Near Chepstow - Chepstow
9.8 10 reviews
Chepstow
24/07 – 27/07
SG$645/nighttotal: SG$1935 (3 )

3 Bedroom Accommodation In Devauden, Near Chepstow

3 5
cottage , Devauden, near Chepstow
This three-bedroom, three-bathroom cottage near Chepstow, in Devauden, boasts stunning Vale of Usk views and is situated 11km from shops and 1.6km from local pubs and restaurants.
The self-catering property, part of a barn conversion, sleeps six guests and features an open-plan living area with a fully equipped kitchen, dishwasher, Freeview TV, and a private enclosed courtyard with barbecue; private parking for two cars is also available.
Cottage ∙ 4 Bedrooms ∙ 10 Guests - Chepstow
10 4 reviews
Chepstow
01/07 – 02/07
SG$2329/nightfor 1 night

Cottage ∙ 4 Bedrooms ∙ 10 Guests

4 1
cottage , Pilning
Hidden Well, a luxurious barn conversion in Aust, South Gloucestershire, offers easy access to the Severn Bridges and is approximately 10km from Pilning, placing guests within reach of Bristol's attractions including the Clifton Suspension Bridge and SS Great Britain.
This three-bedroom property sleeps up to ten guests and boasts a swimming pool, hot tub, and fully equipped kitchen including a dishwasher, alongside a garden perfect for alfresco dining; nearby attractions include the Aust Wetlands and Wild Place Project.
Cottage ∙ 3 Bedrooms ∙ 5 Guests - Chepstow
Chepstow
27/06 – 04/07
SG$301/nighttotal: SG$2107 (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.
Cottage ∙ 1 Bedroom ∙ 3 Guests - Chepstow
10 1 review
Chepstow
29/08 – 30/08
SG$519/nightfor 1 night

Cottage ∙ 1 Bedroom ∙ 3 Guests

1 2
cottage , Llanvair-Discoed
The Snug, a single-storey cottage, is situated on the outskirts of Llanvair Discoed, Monmouthshire, 5km from Caerwent with its Roman ruins and farmer's market.
This 90 square metre self-catering studio offers a king-size bed and sofa bed sleeping up to three guests, boasting a private patio and easy access to attractions like Caldicot and Chepstow Castles.

Best Chepstow holiday rentals with parking

The Nook - Chepstow
10 1 review
Chepstow
27/06 – 04/07
SG$343/nighttotal: SG$2401 (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.
The Dairy - Chepstow
9.8 153 reviews
Chepstow
01/07 – 02/07
SG$180/nightfor 1 night

The Dairy

1 1
apartment , Tidenham Chase
This charming stone cottage is located just a short walk from Tintern Abbey and its pubs and restaurants, and is situated within the peaceful Gloucestershire countryside, just 3 km from the Forest of Dean. The cottage features a unique upside-down design, with a double bedroom and shower room on the ground floor and an open-plan living area and fully equipped kitchenette on the first floor, and can accommodate up to 2 guests. The cottage has a private garden, a sunny gravelled courtyard, and parking, and is perfect for exploring the surrounding area, with easy access to the Offa's Dyke Path, and is pet-friendly.
Laurel Cottage By Stae-homes - Chepstow
9.2 5 reviews
Chepstow
24/07 – 27/07
SG$356/nighttotal: SG$1068 (3 )

Laurel Cottage By Stae-homes

2 5
house , Magor
This detached cottage in Undy offers a convenient base with free Wi-Fi, on-site parking, and garden access, situated approximately 1.2 kilometers from the village centre and local countryside walks. The 80 square meter property accommodates up to 7 guests, featuring a fully equipped kitchen with a dishwasher, two bathrooms, and provided towels and bed linen for a comfortable stay.
Landau House - Chepstow
8.1 18 reviews
Chepstow
24/07 – 27/07
SG$427/nighttotal: SG$1281 (3 )

Landau House

2 5
apartment , Bristol
Landau House, a family-friendly apartment in Bristol, is situated a short drive from Bristol Parkway station and further from central Bristol attractions such as Bristol Temple Meads and Bristol Cathedral.
This 50 square metre flat offers two bedrooms, one bathroom, sleeps five guests, and includes free private parking, Wi-Fi, and a fully equipped kitchenette; a nearby coffee shop adds convenience.

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 stunning Norman castle with a rich history. The town itself is lovely, with independent shops and pubs. If you're looking for something a little further afield, Tintern Abbey is only a short drive away and is worth a visit.
  • What are the best Airbnb and vacation rentals in Chepstow?

    Broadrock Accommodation - Clock Cottage, Chepstow Town - Welsh Cottage and Sedbury Farm Cottages #2 are the most popular Airbnb and vacation rentals in Chepstow among travelers.

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

    The Offa's Dyke Path runs right through Chepstow, offering stunning views of the Wye Valley. For a shorter walk, try the Chepstow Town Trail, which takes you past some of the town's historic landmarks. If you're a cyclist, the Wye Valley Cycle Path is a great option, with flat, scenic routes.
  • 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 Racecourse hosts horse racing throughout the year. There are also plenty of opportunities for kayaking and canoeing on the River Wye. For something more adventurous, try rock climbing at the Chepstow Climbing Centre.
  • What are the best vacation rentals with a pool in Chepstow?

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

    You're ideally located for exploring the area. You can easily reach the city of Bristol in under an hour, and Cardiff is about an hour and a half away. The historic town of Monmouth is just a short drive up the Wye Valley.
  • 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 offer basic amenities like Wi-Fi, TV, and a washing machine. Many also have private gardens, off-street parking, and a fully equipped kitchen. You'll find some with more luxurious features like hot tubs and swimming pools, depending on your budget.
  • What are the best rentals or Airbnbs with a jacuzzi in Chepstow?

    The best vacation 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?

    Spring and autumn are lovely times to visit Chepstow, with mild weather and fewer crowds. Summer is popular for outdoor activities, but it can get busy. Winter can be chilly, but the town is still charming and there are fewer tourists.

Destinations nearby

Best Chepstow holiday rentals with a balcony

Gorgeous 3 Bed House In Bristol - Chepstow
8.1 14 reviews
Chepstow
24/07 – 27/07
SG$387/nighttotal: SG$1161 (3 )

Gorgeous 3 Bed House In Bristol

1 5
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.
Olli's Cottage-terrace & Jacuzzi Optional - Chepstow
9.7 99 reviews
Chepstow
29/08 – 30/08
SG$326/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.
Luxury 4 House,hot Tub,sleeps 9,wi-fi - Chepstow
10 1 review
Chepstow
08/08 – 10/08
SG$887/nighttotal: SG$1774 (2 )

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

1 7
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.
4 Bed Luxury Stay,hot Tub,sleeps 9,private Parking - Chepstow
Chepstow
08/08 – 10/08
SG$879/nighttotal: SG$1758 (2 )

4 Bed Luxury Stay,hot Tub,sleeps 9,private Parking

1 7
house , Chepstow
This detached house in Chepstow is located 20.9 kilometres from Bristol Parkway Station and 27.4 kilometres from Cabot Circus.
This non-smoking property offers a private hot tub, WiFi, parking, a fully equipped kitchen, and terrace access, accommodating up to 17 guests with 1 bedroom and 2 bathrooms.

Best pet friendly Chepstow holiday rentals

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

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chepstow
9.7 14 reviews
Chepstow
29/08 – 30/08
SG$725/nightfor 1 night

Cottage ∙ 2 Bedrooms ∙ 4 Guests

2 2
cottage
Top Lodge is a two-bedroom holiday home located in the village of Llanvair-Discoed, 4.3 kilometres from Penhow, Monmouthshire, with easy access to the Wye Valley Area of Outstanding Natural Beauty and the coast.
This 105 square metre cottage offers a peaceful setting with a garden, swimming pool, jacuzzi, and parking, perfect for families or couples seeking a relaxing escape.
Six Person Glamping Tent - Chepstow
9.7 7 reviews
Chepstow
27/06 – 28/06
SG$500/nightfor 1 night

Six Person Glamping Tent

1 3
glamping , Old Down
The Six Berth Bell Tent is situated on the grounds of Old Down Estate, a 66-acre property with gardens, woodlands, and an adventure park, located near the River Severn and rolling hills, just 12 kilometres from the historic city of Bristol.
The spacious bell tent offers a glamping experience with a double bed and four single beds, a private garden, and access to the on-site facilities, including a spa, farm shop, and adventure park.
Delightful 3-bedroom Cottage With Log Burner - Chepstow
9.8 90 reviews
Chepstow
29/08 – 30/08
SG$1428/nightfor 1 night

Delightful 3-bedroom Cottage With Log Burner

1 2
apartment , Tutshill
This recently renovated 19th-century cottage is located in the peaceful village of Tutshill, just a 1 kilometre walk from Chepstow across the Welsh border via the old Wye Bridge. The property has excellent ratings for location, cleanliness, and user experience.
This charming house offers 3 bedrooms and 1 bathroom, comfortably accommodating up to 6 guests. The well-equipped kitchen, cosy living room with a wood-burning stove, and private enclosed garden with a summer house for storage provide everything you need for a relaxing and enjoyable stay.
The Old Farmhouse - Chepstow
9.5 25 reviews
Chepstow
08/08 – 10/08
SG$708/nighttotal: SG$1416 (2 )

The Old Farmhouse

4 7
house , Blakeney
The Old Farmhouse is situated in Blakeney, just 16 kilometres from Tintern Abbey and 30 kilometres from Bristol Zoo, offering a peaceful retreat in the beautiful countryside. The property has consistently received excellent ratings for cleanliness, location, and overall user experience.
This spacious house features four bedrooms, accommodating up to eight guests. A fully equipped kitchen, including a dishwasher, a private garden, and free parking are provided for your comfort and convenience.
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