Chepstow holiday lettings

We found 223 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
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.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

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:

  • Chepstow Racecourse (1 mi / 1.6 km)
  • St. Pierre Country Club (2.4 mi / 3.9 km)
  • The Wave (7.3 mi / 11.7 km)
  • Puzzlewood (9.8 mi / 15.8 km)
  • Coldra Woods (11.4 mi / 18.4 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:

  • Symonds Yat Rock (0.7 mi / 1.1 km)
  • Wye Valley (7.9 mi / 12.8 km)
  • Aztec West Business Park (8.1 mi / 13.1 km)
  • Puzzlewood (9.8 mi / 15.8 km)
  • Slimbridge Wildfowl and Wetlands Centre (13.5 mi / 21.7 km)
  • Forest of Dean (13.6 mi / 21.9 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?

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 rental accommodation in Chepstow?

Based on our data, cottages are the most popular holiday rental type in Chepstow. But as you'd expect, everyone's idea of an epic stay isn't going to be the same. Vrbo 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 rental 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 Vrbo holiday rentals 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 Vrbo. 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 rentals in Chepstow?

With nine holiday rentals that welcome pets, your furry buddy can join in on your Chepstow getaway. Use our filter tool to search our pet-friendly holiday rentals and find a holiday home that'll set tails wagging on Vrbo.

What are popular rental amenities in Chepstow?

Some of the most popular rental 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, Vrbo holiday homes provide the best amenities for beginning new traditions with the people you cherish the most.

Are there large group holiday rentals in Chepstow?

Take your pick of three Vrbo 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 rentals 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 rentals in Chepstow?

Chepstow has three one-bedroom rentals on offer. Typically located in prime areas because of their smaller size, a one-bedroom rental 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 rentals in Chepstow?

Select from five two-bedroom holiday rentals 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 rentals with WiFi in Chepstow?

Chepstow has two holiday rentals 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 Vrbo homes make it a cinch to go online.

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