Chepstow holiday rentals

We found 344 holiday rentals — enter your dates for availability
Select from 13 homes, 33 cottages and other holiday rentals in Chepstow to find one that's 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

  • Chepstow Castle: Explore one of the oldest stone castles in Britain, steeped in history and offering stunning views of the Wye Valley.
  • Chepstow Museum: Discover local heritage and fascinating exhibits that showcase the town's rich history and culture.
  • Riverside Walks: Enjoy picturesque strolls along the River Wye, perfect for nature lovers and outdoor enthusiasts.
  • Historic Churches: Visit the impressive St. Mary’s Church, known for its beautiful architecture and serene atmosphere.
  • Chepstow Racecourse: Experience the excitement of horse racing at this vibrant venue, hosting a variety of events throughout the year.

Popular types of accommodation in Chepstow

If you're exploring Chepstow, Wales for your next getaway, our holiday rentals offer a range of accommodation options to suit every traveller. Enjoy the charm of Chepstow with popular choices like apartments, cottages, private holiday homes, and even unique storey holiday rentals or a shepherd's hut. Discover ideal accommodation and immerse yourself in local attractions, landmarks, and experiences that make Chepstow a perfect destination for a relaxed, memorable break.

  • Apartments: Highly sought-after urban flats, offering modern conveniences and central locations for a quintessential Chepstow stay.
  • Cottages: Charming rural retreats, providing a cosy, traditional ambiance in the heart of the countryside.
  • Private Holiday Homes: Secluded residences ideal for families or groups, ensuring privacy and a home-away-from-home experience.
  • Cabins: Quaint, rustic lodgings perfect for a serene escape, blending simplicity with comfort.
  • Guest Houses: Welcoming, intimate lodgings that offer a personal touch and homely atmosphere.**

Top attractions in and around Chepstow

Chepstow in Wales offers a rich blend of history and natural beauty. Visitors can explore its renowned castle, historic church, and urban parks, all set against a scenic backdrop perfect for outdoor adventures and cultural exploration. Highlights include the Chepstow Museum, the lively racecourse, and the captivating Chepstow Castle, ensuring a memorable holiday experience steeped in romance and local charm.

  • Tintern Abbey: Explore the evocative ruins that echo centuries of history and cultural tales in Chepstow, perfect for contemplative walks.
  • Chepstow Castle: Discover this majestic fortress, a romantic emblem of the town's medieval past, offering scenic vistas and historic intrigue.
  • Wye Valley: Venture into this vibrant valley 13km away, renowned for its outdoor pursuits and adventurous spirit, inviting nature enthusiasts to explore its rugged beauty.

Things to do recommended for couples

Experience a romantic escape in Chepstow; wander hand in hand through historic streets and enjoy a cosy riverside walk. Delight in local cuisine and embrace the charm of Wales on your couple's retreat.

Things to do recommended for families

Families visiting Chepstow can explore the stunning Chepstow Castle, enjoy a fun day at the nearby Puzzlewood with its enchanting woodland, and take a leisurely walk along the Wye Valley, where kids can spot wildlife and enjoy picnics amidst beautiful scenery.

Things to do recommended for groups

Groups visiting Chepstow can experience thrilling adventures at Go Ape in the Forest of Dean, located 18km away, or at Forest of Dean Adventure Ropes, 19km away, both offering outdoor escapades and invigorating rope courses.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're travelling with a group, family, pets, or planning an extended stay, be sure to refine your search based on your specific needs. Here are some helpful booking tips for using Stayz.

  • Traveling to Chepstow with a group: Think about how many bedrooms you'll require, as well as any amenities like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Stayz.
  • Traveling to Chepstow with young kids: Travelling with young children can present its difficulties. It’s essential to prioritise their comfort and safety, as well as ensure access to suitable facilities, like a private swimming pool. Additionally, it's wise to consider 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 you can relate, take a look at Stayz properties that welcome pets. Most of these pet-friendly accommodations come equipped with 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 that offer special deals for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding amenities such as a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay in and around Chepstow

Chepstow, a charming town in Monmouthshire, offers a blend of history and scenic riverside walks. Stroll the historic streets, visit the impressive local landmarks, and immerse yourself in the friendly, relaxed atmosphere. Ideal for outdoor adventures, Chepstow provides a range of leisurely activities, from riverside explorations to historical site visits, ensuring a memorable and budget-friendly experience.

  • Bristol: Bristol is a vibrant metropolis located 21km away from Chepstow. It is renowned for offering travellers an impressive blend of outdoor pursuits, adventure, and scenic views. Visitors can enjoy diverse activities ranging from exploring expansive shopping centres and educational venues to immersing themselves in the natural splendour of nearby national parks and state monuments. The city’s urban energy and cultural vibrancy provide a unique setting for both relaxation and exploration.
  • Monmouth: Monmouth is a charming city situated 19km away from Chepstow. It is celebrated for its picturesque landscapes and outdoor adventures, making it a popular destination for those seeking both relaxation and excitement. The city offers a variety of recreational experiences, including leisurely strolls through well-maintained golf courses and tranquil recreational areas. Its proximity to national parks and valleys enriches the travel experience with a touch of natural beauty and historical intrigue.
  • Tidenham: Tidenham is a quaint village located within the Chepstow area. Known for its inviting outdoor and adventure spirit, it provides a serene escape with scenic vistas and ample opportunities for leisurely pursuits. Visitors can explore local recreational areas, enjoy refined golfing experiences, and discover the historic charm of nearby castles and valleys. Tidenham offers a peaceful retreat that is both culturally enriching and immersed in nature’s splendour.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 Stayz is simple

If you’re aiming to save on your upcoming journey, you might want to consider being flexible with your travel dates as prices can vary. Additionally, booking a longer stay typically offers significant savings. To find the ideal Stayz property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz's Trip Board provides a convenient space for you to plan new adventures, refine your existing arrangements, or manage your bookings effortlessly. Your saved or reserved properties are thoughtfully categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.stayz.com.au/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)
  • Clearwell Caves (9.3 mi / 14.9 km)
  • Puzzlewood (9.8 mi / 15.8 km)
  • Clifton Down (12.3 mi / 19.7 km)
  • Slimbridge Wildfowl and Wetlands Centre (13.5 mi / 21.7 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.
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.
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 Stayz.
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.
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.
Are all fees included in the Chepstow holiday homes prices shown on Stayz?
Stayz 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.
Are there any Chepstow holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Chepstow holiday homes?
You can find great discounts on holiday homes in Chepstow on Stayz, 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.
Can I change or cancel my Chepstow holiday home booking on Stayz?
To find Chepstow holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chepstow?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Chepstow holiday home?
Book your Chepstow holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chepstow?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chepstow to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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