Chepstow holiday lettings

We found 255 holiday rentals — enter your dates for availability

Discover a selection of 9 homes and other holiday rentals in Chepstow that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you expect for your stay, which might include Wi-Fi and a washer and dryer. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

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Why visit Chepstow

  • Historic Castle: Explore the iconic Chepstow Castle, which boasts a rich history and stunning architecture.
  • Outdoor Adventures: Enjoy various outdoor activities in the beautiful countryside surrounding Chepstow, perfect for nature lovers.
  • Charming Accommodation: Choose from a variety of cosy cottages and holiday homes for a delightful stay.
  • Friendly Atmosphere: Experience the welcoming spirit of the local community as you stroll through shops and parks.
  • Picturesque Surroundings: Discover nearby towns and breathtaking landscapes for a relaxing escape.

Popular types of accommodation in Chepstow

If you're considering a getaway in Chepstow, you're in for a treat with a variety of charming accommodation options. Our most popular choices include apartments, cosy cottages, and houses. Whether you're seeking properties from private landlords, ground floor bungalows, or spacious bedroom flats, we have a range of available rentals to suit your needs. Enjoy your stay with transparency and reassurance as you explore this picturesque town.

  • Apartments: The top choice for holidaymakers in Chepstow, offering modern comforts and convenient locations.
  • Cottages: A delightful option, these quaint homes provide a charming and homely atmosphere for a relaxing getaway.
  • Houses: Ideal for families or groups, these fully-equipped homes offer privacy and space.
  • Cabins: Perfect for those seeking a rustic escape, nestled in nature for a peaceful retreat.
  • Caravan Parks: A popular choice for a fun and affordable camping experience, ideal for families and outdoor enthusiasts.**

Top attractions in and around Chepstow

Chepstow is an ideal destination for outdoor enthusiasts, offering a range of adventures and sports. Visitors can explore notable attractions such as the historic castle, modern colleges, and urban parks, making it a perfect blend of culture and nature. Whether you seek a vibrant city experience or tranquil outdoor pursuits, Chepstow has something to delight every traveller.

  • Tintern Abbey: Explore the stunning ruins of this 12th-century Cistercian monastery, surrounded by lush greenery. Its rich cultural history and serene atmosphere offer a perfect setting for reflection and photography.
  • Wye Valley: Embark on an adventure in this picturesque valley, renowned for its breathtaking scenery and outdoor activities, including hiking, cycling, and kayaking along the River Wye.
  • Chepstow Castle: Discover the impressive medieval architecture of this castle, which boasts romantic views of the Wye River and a fascinating history dating back to the 11th century.

Things to do recommended for couples

Chepstow offers delightful couple experiences! Enjoy thrilling water sports at The Wave, just 4.3km away, or indulge in romance at Parva Farm Vineyard, right in Chepstow. For a lively night, head to the O2 Academy, 8.1km away, for unforgettable music and entertainment.

Things to do recommended for families

During your family vacation in Chepstow, enjoy the tranquility of Dewstow Gardens & Hidden Grottoes, just 3.1km away. For adventure, head to West Country Water Park, 5.6km distant, or explore the entertaining Clifton Downs and Observatory, located 8.1km from Chepstow.

Things to do recommended for groups

In Chepstow, groups can enjoy a day at The Mall at Cribbs Causeway for shopping and entertainment, catch a show at the Bristol Hippodrome Theatre for a cultural experience, and explore the enchanting outdoor beauty of Puzzlewood for a unique adventure.

What do I need to keep in mind when booking a vacation in 'Chepstow

If you’re travelling with a group, family, or pets, or if you’re seeking extended stays, be sure to apply the appropriate filters based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chepstow with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Chepstow with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chepstow: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chepstow: If you're in search of holiday rentals with special offers for stays of a month or more, you’ve come to the perfect place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Chepstow

Chepstow, a charming city in Monmouthshire, offers a delightful blend of historical sites and outdoor adventures. Nestled in the stunning countryside, visitors can explore local shops and enjoy a friendly atmosphere. Just a short distance away, the picturesque towns and breathtaking landscapes provide a relaxing escape for families and budget-conscious travellers alike. Whether you're seeking adventure or a peaceful retreat, Chepstow and its surrounding areas promise an unforgettable experience.

  • Bristol: Bristol is a vibrant city located approximately 8.1km from Chepstow. Known for its rich maritime history and cultural diversity, it offers an exciting blend of outdoor adventures and urban experiences. Visitors can explore the expansive parks and scenic views along the Avon Gorge, while the city centre boasts a variety of shopping centres and educational venues. Notable attractions include the iconic Clifton Suspension Bridge and Bristol Zoo Gardens, providing a delightful mix of history and nature for all ages.
  • Tintern: Nestled within the picturesque Wye Valley, Tintern is a charming village that lies close to Chepstow. It is renowned for its stunning natural surroundings and the historic Tintern Abbey, which attracts numerous visitors. Outdoor enthusiasts can enjoy various recreational areas and scenic walks through the lush landscape, while the village offers quaint shops and local golf facilities. The tranquil beauty of the valley and the proximity to the national park make Tintern an idyllic spot for relaxation and exploration.
  • Tidenham: Tidenham, a quaint village situated near Chepstow, is a hidden gem for those seeking outdoor delights. Surrounded by beautiful valleys and nature trails, it provides ample opportunities for hiking and outdoor pursuits. Visitors can enjoy local shopping centres and recreational areas, making it a convenient base for exploring the surrounding countryside. Close to the scenic beach and national park, Tidenham is perfect for those looking to immerse themselves in nature while enjoying the charm of a small village.

Best time to go to Chepstow

If you're planning a trip to Chepstow, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and July to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.6°F (4.8°C)Light RainMostly CloudyAverageSlightly Low
February41.5°F (5.3°C)Light RainMostly CloudyAverageSlightly Low
March43.9°F (6.6°C)Light RainMostly CloudyAverageAverage
April47.8°F (8.8°C)Light RainMostly CloudySlightly HighAverage
May53.2°F (11.8°C)Light RainMostly CloudyAverageAverage
June58.6°F (14.8°C)Light RainMostly CloudyAverageAverage
July62.1°F (16.7°C)Light RainMostly CloudySlightly HighSlightly High
August61.2°F (16.2°C)Light RainMostly CloudySlightly HighSlightly High
September57.7°F (14.3°C)No Rain (Dry)Mostly SunnyAverageAverage
October52.7°F (11.5°C)Light RainMostly CloudySlightly LowAverage
November46.4°F (8.0°C)Light RainMostly CloudySlightly LowSlightly Low
December42.8°F (6.0°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, refine your existing arrangements, or manage your bookings. Your saved or booked properties are neatly categorised into Potential, Upcoming, or Current Trips. To delve into your Trip Boards, simply head over to: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Explore the riverfront setting in Chepstow

The area's history and cathedral are just some of the reasons to come on holiday to Chepstow. Travellers especially like the golfing, spas and bars in this welcoming and relaxing city. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Chepstow

Are you searching for attractions to see in the area? Venture out of your holiday home and experience everything that Chepstow has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • St. Pierre Country Club (2.4 mi / 3.9 km)
  • The Wave (7.3 mi / 11.7 km)
  • Bristol Zoo Project (8 mi / 12.9 km)
  • Puzzlewood (9.8 mi / 15.8 km)
  • Celtic Manor Resort Golf Club (11.4 mi / 18.4 km)
  • Noah's Ark Zoo Farm (13.3 mi / 21.3 km)

Exploring the natural landscape of Chepstow

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Chepstow is a great place to get outside. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Wye Valley (7.9 mi / 12.8 km)
  • Aztec West Business Park (8.1 mi / 13.1 km)
  • Lydney Harbour (8.1 mi / 13.1 km)
  • Clearwell Caves (9.3 mi / 14.9 km)
  • Puzzlewood (9.8 mi / 15.8 km)
  • Leigh Woods (12.4 mi / 20 km)

Travelling to and around Chepstow

The nearest airport is in Bristol International Airport (BRS), located 17.8 mi (28.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Cardiff International Airport (CWL), which is 33.2 mi (53.4 km) away.

If you prefer train travel, you can make your way to Chepstow Station.

Frequently asked questions

What is the best area to stay in Chepstow when booking a holiday rental?
When considering a holiday rental in Chepstow, a popular area to stay is near the town centre. This vibrant locality offers a charming blend of historic architecture and modern conveniences. Staying here places you within walking distance of top attractions such as the impressive Chepstow Castle, which dates back to the 11th century, and the scenic Wye Valley, known for its stunning landscapes and outdoor activities.

The town centre is home to a variety of properties, ranging from quaint cottages to more contemporary apartments, ensuring there is something to suit every taste and budget. Additionally, being centrally located means you can easily explore the local shops, cafes, and restaurants, enhancing your overall experience in this picturesque area.

Another lovely option is to consider properties in the vicinity of the River Wye, where you can enjoy beautiful views and easy access to riverside walks. This area is great for those looking to immerse themselves in nature while still being close to the town's amenities and attractions.
How much does it cost to rent a holiday home in Chepstow?
Prices for holiday rentals in Chepstow vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chepstow to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chepstow holiday house rentals?
You can find great discounts on house rentals in Chepstow on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Chepstow?
In Chepstow, cottages are the most popular holiday rental option, with around 87 available throughout the charming town. These cottages typically feature traditional Welsh architecture and provide a cosy atmosphere, complete with fully equipped kitchens, comfortable living areas, and often a garden or outdoor space for enjoying the picturesque surroundings.

For those seeking additional space, there are about 18 holiday houses that cater to larger groups or families, offering multiple bedrooms and more extensive amenities. There are also several apartments and villas available, which provide modern comforts and convenient access to local attractions such as Chepstow Castle and the scenic Wye Valley.
Are there any family house rentals in Chepstow?
In Chepstow, there are numerous family-friendly house rentals available, with around 18 options to choose from. This charming town, situated near the beautiful Wye Valley, offers a fantastic base for families looking to explore the area. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and enjoy the fresh air.

Visitors will appreciate the proximity to local attractions such as Chepstow Castle, a historic site that provides insight into the area's rich heritage, and the scenic walking trails along the River Wye, superb for family outings. Additionally, the nearby Forest of Dean offers a wealth of outdoor activities, including cycling and hiking opportunities.
Can I rent a holiday home with a pool or hot tub in Chepstow?
In Chepstow, there are several holiday homes available for rent that feature pools or hot tubs, making it a great destination for those seeking relaxation and leisure. This charming town, located near the scenic Wye Valley, offers properties with a range of amenities. Many of these rentals come equipped with private swimming pools, inviting hot tubs, and outdoor spaces great for enjoying the beautiful Welsh countryside.

Travellers can also expect fully equipped kitchens, spacious living areas, and comfortable bedrooms, suiting families or groups looking for a home away from home.
Can I find long-stay holiday rentals in Chepstow?
A long-stay holiday rental in Chepstow is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Chepstow?
In Chepstow, there are numerous pet-friendly house rentals available, offering a range of options for travellers seeking a comfortable stay. Many of these properties come equipped with amenities such as fully furnished kitchens, spacious living areas, and private gardens, great for those travelling with pets.

The town itself is rich in history and boasts easy access to beautiful outdoor spaces. Nearby, the Wye Valley Area of Outstanding Natural Beauty provides stunning landscapes and numerous walking trails where pets are welcome, making it an ideal location for nature lovers. Additionally, Chepstow is close to the scenic Chepstow Castle, offering a fascinating glimpse into the region's heritage. See all pet-friendly rentals in Chepstow.
Are there any remote work holiday rentals in Chepstow?
In Chepstow, Wales, there are numerous options for remote work holiday rentals, with around 114 available throughout the area. This charming town, known for its historic castle and scenic location along the River Wye, provides a great backdrop for work and leisure. Many of the properties feature essential amenities such as reliable Wi-Fi, allowing for seamless connectivity during your stay.

Travellers can expect a variety of accommodations, from cosy apartments in the town centre to larger houses with dedicated workspaces. Many rentals also offer comfortable living areas, fully equipped kitchens for self-catering, and some may even provide outdoor spaces for a refreshing break during the workday. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chepstow holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chepstow with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chepstow?
In Chepstow, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties are pet-friendly, accommodating both pets and service animals, making it a great choice for those travelling with furry companions. Onsite parking is also a common feature, providing convenient access for visitors arriving by car. Additionally, several rentals include a fireplace, which adds a cosy touch for those chilly evenings.
When is the best time to visit Chepstow for a holiday rental?
The peak travel season in Chepstow is during the summer months, particularly from July to September. This vibrant period attracts families and outdoor enthusiasts keen to explore the scenic beauty of the Wye Valley and partake in various activities, including hiking and kayaking. The charming town comes alive with visitors enjoying its rich history, quaint streets, and the stunning Chepstow Castle, all while basking in the warmth of the British summer.

July stands out as the most popular month for travel to Chepstow, offering pleasant temperatures averaging between 15 to 25 degrees Celsius. This comfortable climate encourages outdoor adventures and leisurely strolls along the River Wye, where you can soak in the picturesque surroundings and perhaps spot some local wildlife. Festivals and events also abound in this season, providing a fantastic opportunity to engage with the local culture.

For those seeking a more budget-friendly option, November is an excellent choice. The town experiences fewer tourists during this low season, allowing for a more peaceful experience while exploring Chepstow's attractions. This time of year also offers a unique charm, with autumnal hues painting the landscape, superb for scenic walks and enjoying the local cuisine in a quieter atmosphere.

Ultimately, the best time to visit Chepstow for a holiday rental hinges on your preferences—whether you wish to revel in the lively summer atmosphere or enjoy the serene beauty of autumn.
How early should I book a Chepstow holiday rental?
Book your Chepstow holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chepstow?
In Chepstow, visitors can explore a variety of attractions that highlight the town's rich history and beautiful surroundings. A prominent feature is Chepstow Castle, one of the oldest surviving stone castles in Britain, which offers stunning views of the River Wye and an insight into medieval architecture. The nearby Chepstow Bridge, a historic structure that spans the river, is also worth a visit for its impressive design and scenic views.

The town's location makes it a gateway to the Wye Valley Area of Outstanding Natural Beauty, ideal for those who enjoy outdoor activities like hiking and cycling along the picturesque riverbanks. Just a short distance away is the Tintern Abbey, a stunning ruin that dates back to the 12th century, set against a backdrop of lush greenery.

For those interested in local culture, Chepstow hosts various markets and events throughout the year, providing a taste of Welsh traditions and community spirit. The town centre features quaint shops, cafes, and restaurants, making it a superb spot to relax after a day of exploration.
Can I change or cancel my Chepstow home rental booking on Vrbo?
To find Chepstow holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chepstow holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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