Chepstow holiday rentals

We found 343 holiday rentals — enter your dates for availability
Select from 11 homes, 34 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)
  • Cattle Country Adventure Park (10.4 mi / 16.8 km)
  • Celtic Manor Resort Golf Club (11.4 mi / 18.4 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 home?
Tidenham is one of the most popular areas to get a holiday home in Chepstow. Take a look at our collection of comfortable stays and then get ready to discover this destination like a local.
What is the most popular type of holiday home accommodation in Chepstow?
Based on our data, cottages are the most popular holiday home type in Chepstow. But as you'd expect, everyone's idea of an epic stay isn't going to be the same. Stayz has holiday homes of all shapes and sizes, so you're sure to discover the perfect match.
How much does it cost to rent a holiday home in Chepstow?
Length of stay, property type and time of year are some of the conditions that can determine the price of a holiday home. Simply add your travel dates to find your ideal fit. From comfy cabins to plush villas, all Stayz holiday homes offer terrific value.
How much does it cost to rent a beach house in Chepstow?
When you travel and the size and style of the property will influence the cost of your beachside escape. Type in your Chepstow travel dates to view your available options on Stayz. Can't live without a hot tub? Use the filters to select the features and amenities you want in your beach house.
Are there pet-friendly holiday homes in Chepstow?
With nine holiday homes that welcome pets, your furry buddy can join in on your Chepstow getaway. Use our filter tool to search our pet-friendly holiday homes and find a holiday home that'll set tails wagging on Stayz.
What are popular home amenities in Chepstow?
Some of the most popular home amenities people are searching for in Chepstow are tennis, a barbecue grill and a fireplace. Whether you're on the road with family, friends or even pets, Stayz holiday homes provide the best amenities for beginning new traditions with the people you cherish the most.
Are there large group holiday homes in Chepstow?
Take your pick of three Stayz properties in Chepstow that can accommodate a group of five or more guests. You'll get all the space and privacy you need to spend time with your nearest and dearest — and nobody else.
Are there holiday homes in Chepstow that welcome kids?
Gather your whole family for a memorable adventure in Chepstow at one of our nine family-friendly properties. These stays offer conveniences that are perfect for getaways with the little ones, such as laundries, bunk beds and swimming pools. Just click on the "Properties good for families" filter box and pick your favourite.
What are the top attractions for families in Chepstow?
You'll find loads of fabulous things to do and see with the family in Chepstow, such as:

  • Chepstow Castle
  • The Wave
  • Caldicot Castle

Are there one-bedroom holiday homes in Chepstow?
Chepstow has three one-bedroom homes on offer. Typically located in prime areas because of their smaller size, a one-bedroom home is great if you're travelling with your partner or a pal. And with plenty of home comforts like kitchens and more privacy than a standard hotel, you'll be able to relax while sightseeing around this exciting destination.
Can I find two-bedroom holiday homes in Chepstow?
Select from five two-bedroom holiday homes in Chepstow. Put your little ones in the second room or fill it with a couple of your nearest and dearest friends. There's space for whoever's lucky enough to be joining your adventure.
Are there holiday homes with WiFi in Chepstow?
Chepstow has two holiday homes with WiFi, so you can stay connected when you're away. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming TV shows with the family to catching up on social media, these Stayz homes make it a cinch to go online.
How old do you have to be to rent a holiday home in Chepstow?
The minimum age allowed can vary across properties on Stayz, so be sure to check the rules of the holiday home in Chepstow you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Chepstow for?
How long you can rent a holiday home in Chepstow varies according to the property. Just enter your desired dates to view a list of options offering extended stays. With tons of creature comforts such as washing machines and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find a terrific place to call your home away from home in Chepstow.