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Holiday Rentals in Chepstow

67 available vacation rental offers

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Best Holiday rentals and Airbnb offers in Chepstow

Anne's Hut Monmouthshire - Chepstow
Chepstow
2 1
SG$252/nighttotal: SG$1764 (7 )

Anne's Hut Monmouthshire

house - Saint Arvans
This one-bedroom holiday cottage in Saint Arvans, Monmouthshire, is situated 26 kilometres from Bristol Parkway Station and within a 34-kilometre radius of Bristol's key attractions.
This dwelling offers a fully equipped kitchen, a fireplace, a garden with a barbecue area, and WiFi, accommodating up to two guests with a 10:00 AM check-out.
The Willow - Studio 17 - Chepstow
Chepstow
2 1
SG$96/nighttotal: SG$14400 (150 )

The Willow - Studio 17

studio - Patchway
This self-contained studio apartment in North Bristol offers convenient access to major employment centres, with Aerospace and Airbus approximately 5 kilometres away and Aztec West just 2 kilometres distant.
This modern studio, ideal for two guests, features a 60 square metre floor area, a well-equipped kitchenette including a fridge, and access to communal laundry facilities, all within a 7-kilometre drive of The Mall at Cribbs Causeway.
Stone Cottage With A Splendid Wye Valley View - Chepstow
9.9 111 reviews
Chepstow
4 2
SG$394/nighttotal: SG$1970 (5 )

Stone Cottage With A Splendid Wye Valley View

cottage - Hewelsfield and Brockwear
This charming cottage is located just a short distance from the village of Brockweir, offering stunning views of the River Wye and the surrounding countryside. It has received excellent ratings for its location, cleanliness, and overall experience.
The cottage has two bedrooms and one bathroom, accommodating up to four guests. It features a well-equipped kitchen, a private balcony and garden, and a wood-burning stove for cosy evenings.
Broadrock Accommodation - Clock Cottage - Chepstow
9.7 153 reviews
Chepstow
2 1
SG$283/nighttotal: SG$1132 (4 )

Broadrock Accommodation - Clock Cottage

apartment - Chepstow
This apartment is located in Chepstow, within the Wye Valley, a 40-minute drive from Bristol and Cardiff. It's rated excellent for location, cleanliness, and user experience, making it a great choice for travellers.
The apartment is self-catering, with a kitchen equipped with a fridge, microwave, and dishwasher. It also has a terrace or balcony, a garden, a restaurant, a fitness centre, a tennis court, parking, and internet access.
Home In Bradley Stoke, Bristol - Chepstow
8.7 3 reviews
Chepstow
4 2
SG$274/nighttotal: SG$1370 (5 )

Home In Bradley Stoke, Bristol

apartment - Bristol
This Bradley Stoke flat in Bristol is conveniently located 2.6 kilometres from Bristol Parkway Station, with Cabot Circus 11.1 kilometres away.
This two-bedroom apartment offers private parking, air conditioning, and complimentary WiFi, accommodating up to 11 guests.
Luxurious Severn Chalet With Hot Tub - Chepstow
9.5 99 reviews
Chepstow
4 2
SG$254/nighttotal: SG$1270 (5 )

Luxurious Severn Chalet With Hot Tub

cabin
This Woolaston lodge offers uninterrupted panoramic views of the Severn Estuary, with the Severn Bridge and Prince of Wales Bridge visible on clear days, and is situated a short 5-kilometer drive from Lydney.
This serene two-bedroom, two-bathroom lodge accommodates up to four guests and features a kitchen, Wi-Fi, a jacuzzi, and parking, providing a tranquil base for exploring the Forest of Dean.
Hopewell Barn - Chepstow
Chepstow
2 3
SG$299/nighttotal: SG$2093 (7 )

Hopewell Barn

house - Hewelsfield
Hopewell Barn, a detached house in Hewelsfield, is situated approximately 32 to 42 kilometres from Bristol Parkway Station and Bristol Cathedral, offering a countryside retreat.
This property accommodates up to 9 guests in 3 bedrooms and 2 bathrooms, featuring a dishwasher, fireplace, garden, and private parking with an electric vehicle charging point.
3 Bedroom Home In The Heart Of Caldicot - Chepstow
8.9 17 reviews
Chepstow
4 3
SG$297/nighttotal: SG$1485 (5 )

3 Bedroom Home In The Heart Of Caldicot

apartment
This 3-bedroom flat is located in Caldicot, Monmouthshire, 500 meters from Caldicot Castle and close to local amenities and major transport links.
This property accommodates up to 6 guests and features a fully equipped kitchen with a fridge, freezer, and microwave, along with free Wi-Fi and heating for a comfortable stay.
The Potting Shed At Mathern Palace - Chepstow
9.7 48 reviews
Chepstow
2 2
SG$324/nighttotal: SG$1296 (4 )

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.
Anne's Hut - Chepstow
10 4 reviews
Chepstow
2 1
SG$252/nighttotal: SG$1764 (7 )

Anne's Hut

cabin
Anne's Hut is a secluded shepherd's hut retreat located in a meadow on the edge of a wood near the ancient settlement of Penterry, just 5km from Chepstow and 10km from Tintern. The accommodation has received excellent ratings from previous guests for its cleanliness, location and overall experience.
The charming hut comprises two linked shepherd's huts, providing a comfortable space for two guests. The hut features a wood-burning stove, a well-equipped kitchen, a comfortable super-king size bed, a luxurious bathroom with a double-ended bath and rain shower, a decking patio area, and a fire pit and barbecue for outdoor cooking and relaxation.
Gardeners Cottage At Mathern Palace - Chepstow - Chepstow
10 2 reviews
Chepstow
4 2
SG$283/nighttotal: SG$1415 (5 )

Gardeners Cottage At Mathern Palace - Chepstow

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.
Welsh Countryside Lodge Fully Accessible Sleeps 6 - Chepstow
9.9 129 reviews
Chepstow
2 3
SG$421/nighttotal: SG$2947 (7 )

Welsh Countryside Lodge Fully Accessible Sleeps 6

bungalow
This charming bungalow is located in the peaceful hamlet of Llanfihangel-Tory-Mynydd, just 10km from the historic town of Chepstow and within easy reach of the Wye Valley. It has received excellent ratings for its location, cleanliness, and overall experience.
The property offers comfortable accommodation for up to 6 guests, with 3 bedrooms and 2 bathrooms. It includes a well-equipped kitchen with a freezer, microwave, and dishwasher, a private garden with a table and chairs, and parking for two vehicles.

Best family friendly Chepstow holiday rentals

Among the 67 accommodations in Chepstow, here are the 4 best family friendly rentals

The Old Rectory With Swimming Pool - Chepstow
9.7 38 reviews
Chepstow
2 5
SG$881/nighttotal: SG$6167 (7 )

The Old Rectory With Swimming Pool

apartment
This five-bedroom country house near Oldbury-on-Severn, Gloucestershire, offers a tranquil escape less than 60km from Bath and 45km from Bristol.
Sleeping up to ten guests, the property boasts a heated swimming pool (open May-September), tennis court, two acres of private gardens, a well-equipped kitchen, and ample parking.
Large Modern Home, Free Parking, Families And Contractors Welcome - Chepstow
8.6 13 reviews
Chepstow
4 3
SG$590/nighttotal: SG$2950 (5 )

Large Modern Home, Free Parking, Families And Contractors Welcome

house - Bristol
This spacious Bristol house is situated 4.3km from Bristol Parkway Station and 11km from Clifton, offering easy access to both the station and the Clifton Suspension Bridge.
The 95 square metre property sleeps up to 11 guests in three bedrooms, two bathrooms, and boasts free Wi-Fi, parking, a garden, and a fully equipped kitchen including a microwave and dishwasher.
Modern 2-bedroom Apartment - Chepstow
8.6 176 reviews
Chepstow
4 2
SG$291/nighttotal: SG$1455 (5 )

Modern 2-bedroom Apartment

apartment - Bristol
This modern two-bedroom flat is located in Bristol, just 3.7 kilometres from Bristol Parkway Station and 9.3 kilometres from Bristol Zoo, in a quiet area convenient for exploring the city. The property has received excellent ratings for cleanliness, user experience, and location, making it a great choice for travellers.
The flat offers 59 square metres of space, comfortably accommodating up to five guests. It comes equipped with a fully fitted kitchen, free Wi-Fi, and parking, as well as a comfortable living room with a flat-screen TV, ensuring a pleasant and convenient stay.
Cottage ∙ 1 Bedroom ∙ 2 Guests - Chepstow
Chepstow
2 1
SG$198/nighttotal: SG$792 (4 )

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage - Brockweir
Ferryman's Lodge, an idyllic wooden lodge, is situated on the outskirts of Brockweir village, offering countryside views and direct access to walks within the Wye Valley National Landscape, with Chepstow a short drive away. This family-friendly cottage for two features an open-plan living space with a woodburning stove, a double bedroom with an en-suite, a kitchen with a fridge and microwave oven, and a garden with a raised veranda, all within easy reach of Brockweir's pubs, convenience store, and riverside.

Best Chepstow holiday rentals with parking

The Dairy Cottage With Garden And Parking - Chepstow
9.3 32 reviews
Chepstow
2 1
SG$152/nighttotal: SG$22800 (150 )

The Dairy Cottage With Garden And Parking

apartment
The Dairy Cottage apartment is situated in Tockington, a village near Bristol, offering convenient access to the city's attractions (distance unspecified).
This one-bedroom self-catering flat sleeps two guests and includes a fully equipped kitchen, private garden with seating, parking, Wi-Fi, and a bathroom with a bathtub.
Sunny Modern House With Garden - Chepstow
Chepstow
4 2
SG$243/nighttotal: SG$1215 (5 )

Sunny Modern House With Garden

apartment - Bristol
This 2-bedroom house in Bradley Stoke offers convenient access to Bristol city centre, Cribbs Causeway, and major motorway networks, with The Mall at Cribbs Causeway located approximately 2.5 kilometers away.
This property provides Wi-Fi, parking for two vehicles, a private garden, and accommodates up to five guests with a king-size bed, single bed, and sofa bed, ideal for families or small groups visiting Bristol.
14 Birchwood Road, Family Friendly, With Open Fire In Woolaston - Chepstow
10 2 reviews
Chepstow
4 5
SG$511/nighttotal: SG$2555 (5 )

14 Birchwood Road, Family Friendly, With Open Fire In Woolaston

cottage - Lydney
This five-bedroom holiday home, located at 14 Birchwood Road in Woolaston, near Lydney, Gloucestershire, is situated 0.64 km from Tintern Abbey and Gate House, offering easy access to the Wye Valley and Caldicot Castle.
The 160 square metre property sleeps nine guests comfortably, boasting two bathrooms, a well-equipped kitchen with modern appliances, a garden, parking, and WiFi, plus a wood-burning stove.
Chepstow 4br Retreat | Gated, Garden & Parking - Chepstow
Chepstow
2 4
SG$520/nighttotal: SG$78000 (150 )

Chepstow 4br Retreat | Gated, Garden & Parking

apartment
Bloomery Gardens 3 is a spacious 4-bedroom house located in Chepstow, Monmouthshire, providing easy access to the Wye Valley and the town of Chepstow itself.
This contemporary residence offers accommodation for up to 8 guests, featuring a private garden, Wi-Fi, a fully equipped kitchen, and parking for three vehicles, making it an ideal base for exploring the region.

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.

Popular destinations

Best Chepstow holiday rentals with a balcony

Welsh Gatehouse: Historical Castle With Ev Charger - Chepstow
9.9 210 reviews
Chepstow
2 1
SG$280/nighttotal: SG$1120 (4 )

Welsh Gatehouse: Historical Castle With Ev Charger

castle
This castle is located just 1.5 kilometres from St. Pierre Country Club, and within 5 kilometres of both the River Wye and Chepstow Castle, making it a great base for exploring the area. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience.
This one-bedroom castle offers 55 square metres of space, comfortably accommodating up to 2 guests. Enjoy a peaceful retreat with a garden, barbecue facilities, and a terrace, perfect for soaking up the Welsh sunshine.
Bertha Shepherd's Hut - Chepstow
9.8 4 reviews
Chepstow
2 1
SG$245/nighttotal: SG$1715 (7 )

Bertha Shepherd's Hut

house - Lydney
Bertha Shepherd's Hut, a self-catering cottage in Lydney, Gloucestershire, offers a peaceful countryside escape approximately 34-47km from Bristol, providing easy access to attractions like Bristol Parkway Station and Ashton Court.
This one-bedroom hut, sleeping up to three guests, boasts a 20 square metre floor area, a kitchenette with oven and microwave, free Wi-Fi, private parking, a terrace with garden views, and an outdoor fireplace; nearby cycling and hiking opportunities enhance the stay.
Welsh Gatehouse A Historic Castle Retreat That Welcomes Dogs And Electric Vehicles - Chepstow
Chepstow
2 1
SG$332/nighttotal: SG$1328 (4 )

Welsh Gatehouse A Historic Castle Retreat That Welcomes Dogs And Electric Vehicles

gîte - Chepstow
Gîte listing. Your accommodation will be based in Chepstow.
Facilities and services: a kitchen, an iron and free parking.
Welsh Gatehouse A Historic Castle Retreat That Welcomes Dogs And Electric Vehicles - Chepstow
9.5 47 reviews
Chepstow
2 1
SG$332/nighttotal: SG$1328 (4 )

Welsh Gatehouse A Historic Castle Retreat That Welcomes Dogs And Electric Vehicles

house - Mathern
Welsh Gatehouse is a charming cottage located in Mathern, just 23 kilometres from Bristol Parkway Station, offering a peaceful escape from the city. The property has received excellent ratings for its location, cleanliness, and overall experience.
The cottage provides comfortable accommodation for two guests, with one bedroom, one bathroom, and a floor area of 32 square metres. It features a well-equipped kitchen, a private garden with views, a balcony, and parking.

Best pet friendly Chepstow holiday rentals

Among the 67 accommodations in Chepstow, here are the 4 best pet friendly rentals

Charming, Historic Farm Cottage In The Wye Valley - Chepstow
9.9 29 reviews
Chepstow
2 2
SG$284/nighttotal: SG$1988 (7 )

Charming, Historic Farm Cottage In The Wye Valley

apartment
This charming cottage is situated on a 23-acre working farm in the southern Wye Valley, just a short drive from the picturesque village of Woolaston. The cottage is located close to the Forest of Dean, offering easy access to hiking trails and cycling routes.
The cottage sleeps up to four guests in two double bedrooms, one of which is located on the ground floor. The cottage is fully equipped with a modern kitchen, a cosy lounge with a log burner, and two bathrooms. The cottage is also fully accessible for wheelchair users and is ideal for families with pets.
The Elements Residence - Chepstow
Chepstow
2 10
SG$1566/nighttotal: SG$6264 (4 )

The Elements Residence

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.
Orchard Cottage Monmouthshire - Chepstow
10 1 review
Chepstow
2 1
SG$395/nighttotal: SG$1580 (4 )

Orchard Cottage Monmouthshire

house - Saint Arvans
This one-bedroom holiday cottage in Saint Arvans, Monmouthshire, is located approximately 25 kilometres from Bristol Parkway Station and 50 kilometres from Bristol Airport, offering access to Bristol Cathedral and Ashton Court.
This pet-friendly holiday home provides a private garden with a barbecue, a fully equipped kitchen, free WiFi, and is ideal for outdoor pursuits such as golfing, fishing, and cycling.
New, Modern Two Bedroom House, Open Plan Living. - Chepstow
10 1 review
Chepstow
2 2
SG$215/nighttotal: SG$32250 (150 )

New, Modern Two Bedroom House, Open Plan Living.

apartment
This two-bedroom flat in Portskewett offers a peaceful base with convenient access to local amenities and attractions, situated in a tranquil area of the town.
This self-catering accommodation comfortably sleeps four guests and features a fully equipped kitchen, a lounge with TV, an open-plan dining area, and private patio spaces, with parking and internet provided.
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