Best Holiday rentals and Airbnb offers in Chepstow
Chepstow
24/07 – 25/07
SG$1410/nightfor 1 night
Tawny Cottage
1 4
house , Usk
Tawny Cottage in Llandenny offers a peaceful base, located 38 kilometres from Bristol Parkway Station, 45 kilometres from Cabot Circus, and 46 kilometres from Cardiff's Motorpoint Arena and Cardiff University. This 130 square metre holiday cottage accommodates up to 9 guests with 3 bedrooms and 2 bathrooms, featuring a fully equipped kitchen with a dishwasher, complimentary WiFi, private parking, and a garden, with golfing, cycling, and fishing available nearby.
8.3 4 reviews
Chepstow
24/07 – 25/07
SG$1528/nightfor 1 night
Rose Cottage
2 4
house , Lydney
Rose Cottage is located in Lydney, just 35 kilometres from Kingsholm Stadium, 38 kilometres from Bristol Parkway Station, and 45 kilometres from Cabot Circus, offering a peaceful retreat in a charming town. The property has consistently received very good ratings for its location, cleanliness, and overall experience. The cottage features two bedrooms and two bathrooms, spanning 105 square metres and comfortably accommodating up to four guests. A fully equipped kitchen, a private garden, free Wi-Fi, and free parking are provided for your convenience.
Chepstow
29/08 – 30/08
SG$222/nightfor 1 night
The Willow - Studio 14
1 2
studio , Patchway
This self-contained studio apartment in North Bristol is conveniently situated within 5 kilometers of Aerospace, 2 kilometers of Aztec West, and a 7-minute drive from Cribbs Causeway shopping centre, with bus stops directly outside and Patchway Train Station a 15-minute walk away. This modern studio accommodates two guests, offering a kitchenette with a fridge, a double bed, private access, free WiFi, and access to communal laundry facilities, located near leisure attractions such as Wild Place and Bristol Golf Course.
Chepstow
08/08 – 10/08
SG$491/nighttotal: SG$982 (2 )
Entire Barn In Monmouthshire, United Kingdom
1 7
farm , Monmouthshire
This Monmouthshire property offers a rural retreat, situated near Wentwood Forest, the largest ancient woodland in Wales, with the Wye Valley, Vale of Usk, and historic castles at Chepstow, Caldicot, and Raglan within easy reach, and Abergavenny and the Brecon Beacons National Park a 30-minute drive away. This pet-friendly farmhouse accommodates up to seven guests, featuring two bathrooms, a kitchen with an Aga, and internet access, providing a peaceful escape for outdoor pursuits such as walking and cycling.
9.3 44 reviews
Chepstow
01/07 – 31/07
SG$232/nighttotal: SG$6960 (30 )
Orion Drive
1 3
apartment , Gloucestershire du Sud
This apartment is located in Little Stoke, a peaceful residential area just a short drive from the M5 motorway and a 15-minute drive from Bristol Airport. It has received excellent ratings for cleanliness, location and user experience. The apartment has three bedrooms and one bathroom, comfortably accommodating up to four guests. It comes equipped with a kitchen, internet access and is close to local amenities, including shops, restaurants and pubs.
Chepstow
27/06 – 04/07
SG$161/nighttotal: SG$1127 (7 )
Winnies Hut
1 2
cabin , Devauden
This cosy cabin is situated in the Welsh countryside, just 6km from Chepstow and 9km from Usk, offering a peaceful retreat amidst the beauty of the surrounding woodland and wildlife. The one-bedroom cabin comfortably sleeps two guests and features a fully equipped kitchen, providing everything you need for a self-catering stay. Enjoy the absence of Wi-Fi and TV, allowing you to fully immerse yourself in the tranquil surroundings and explore the nearby historical attractions.
Chepstow
21/08 – 30/08
SG$1354/nighttotal: SG$12186 (9 )
4 Bed Luxury Home,sauna,hot Tub,sleeps 9
4 2
house , Chepstow
This luxury 4-bedroom house in Moffat is located 21 kilometres from Bristol Parkway Station and 26 kilometres from Cabot Circus, with Edinburgh Airport situated 97 kilometres away. This 30 square metre property accommodates up to 17 guests and features two bedrooms, two bathrooms, a kitchen with a fridge, microwave oven, and dishwasher, a jacuzzi, garden, sauna, and parking, with check-out between 10:00 AM and 11:00 AM.
Chepstow
29/08 – 30/08
SG$222/nightfor 1 night
The Willow Studios - Flat 2
1 2
studio , Patchway
This self-contained studio flat in North Bristol is located 2 kilometres from Aztec West and 5 kilometres from Aerospace and Airbus, with Cribbs Causeway 7 kilometres away, and features convenient public transport links including bus stops directly outside and Patchway Train Station a 15-minute walk away. The 60 square meter studio offers a comfortable double bed, a kitchenette with a new hob and fridge, complimentary Wi-Fi, and access to communal laundry facilities, accommodating up to two guests.
9.9 123 reviews
Chepstow
21/08 – 30/08
SG$157/nighttotal: SG$1413 (9 )
The Nursery Wing - Wyndcliffe Court
1 2
apartment , St Arvans
This apartment is located just off the Wye Valley walk at Upper Wyndcliff, offering easy access to the beautiful scenery of the Wye Valley and nearby towns like Tintern and Chepstow, all within a 10-kilometer radius. It has consistently received excellent ratings for location, cleanliness, and user experience. The self-catering property has one bedroom and one bathroom, comfortably accommodating up to two guests. Guests can enjoy a modern kitchen, a garden with uneven steps and steep drops, and a relaxing bathroom with a freestanding roll-top bath, all included in the price.
9.9 35 reviews
Chepstow
13/08 – 16/08
SG$413/nighttotal: SG$1239 (3 )
Gardener's Cottage At Mathern Palace
1 4
apartment , Mathern
Gardener's Cottage is a beautifully restored 19th-century Hay Barn located on the grounds of Mathern Palace, a Grade I listed property, just a short walk from the village pub and its network of footpaths. The property has received excellent ratings for its location, cleanliness, and overall experience. The cottage has two bedrooms, one bathroom, and can comfortably accommodate up to four guests. Amenities include a fully equipped kitchen with a fridge and microwave, free parking, and a private garden with access to a shared larger garden.
9.2 140 reviews
Chepstow
29/08 – 30/08
SG$190/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.
Chepstow
21/08 – 30/08
SG$217/nighttotal: SG$1953 (9 )
Ferryman's Lodge
1 2
apartment , Brockweir
Ferryman's Lodge is a single-storey wooden lodge in Brockweir, Gloucestershire, located 200 meters from the River Wye and 200 meters from the village pub. This accessible lodge sleeps two guests, offering an open-plan living space with a woodburning stove, a well-equipped kitchen, a double bedroom with an en-suite shower, WiFi, gas central heating, and a veranda with furniture, with off-road parking available.
Best family friendly Chepstow holiday rentals
Among the 28 accommodations in Chepstow, here are the 4 best family friendly rentals
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.
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.
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.
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
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.
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.
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.
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?
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 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?
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?
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
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.
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.
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.
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
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.
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.
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.
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.