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Chepstow holiday rentals

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Best Chepstow holiday rentals

Most recommended holiday rentals in Chepstow

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Welsh Marches at Upper Glyn Farm - Chepstow - Living room
Welsh Marches at Upper Glyn Farm
Chepstow, WLS, United Kingdom
9.3Wonderful(86)
Free Wi-Fi
Pet-friendly
£171+
Check availability
Broadrock Accommodation - Clock Cottage - Chepstow - Bedroom
Broadrock Accommodation - Clock Cottage
Chepstow, WLS, United Kingdom
8.8Very Good(71)
Parking
Free Wi-Fi
£163+
Check availability
Clock Cottage - Luxury 2 bed Holiday Let - Chepstow - Bedroom
Clock Cottage - Luxury 2 bed Holiday Let
Chepstow, WLS, United Kingdom
Free Wi-Fi
£163+
Check availability
Cider Mill Lodge - Hw7420 - Chepstow - Pool
Cider Mill Lodge - Hw7420
Chepstow, WLS, United Kingdom
9.1Wonderful(8)
Free Wi-Fi
£459+
Check availability
The Honey Pot - Chepstow - Bedroom
The Honey Pot
Chepstow, WLS, United Kingdom
10Wonderful(8)
Free Wi-Fi
£237+
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Welsh Marches - Blorenge - Chepstow - Living room
Welsh Marches - Blorenge
Chepstow, WLS, United Kingdom
Free Wi-Fi
£119+
Check availability
Welsh Marches - Skirrid - Chepstow - Living room
Welsh Marches - Skirrid
Chepstow, WLS, United Kingdom
Free Wi-Fi
£140+
Check availability
Chateau Terrace Georgian House - Chepstow - Bedroom
Chateau Terrace Georgian House
Chepstow, WLS, United Kingdom
8.4Very Good(80)
Free Wi-Fi
Pet-friendly
£70+
Check availability
Wye Valley Countryside Retreat - Chepstow - Dining room
Wye Valley Countryside Retreat
Chepstow, WLS, United Kingdom
9.7Wonderful(86)
£93+
Check availability
Welsh Gatehouse, Historic Castle which can cater for Electric Vehicle - Chepstow - Living room
Welsh Gatehouse, Historic Castle which can cater for Electric Vehicle
Chepstow, WLS, United Kingdom
9.3Wonderful(42)
Parking
Free Wi-Fi
£188+
Check availability
Carpenters Cottages - Chepstow
Carpenters Cottages
Chepstow, WLS, United Kingdom
8.1Very Good(152)
Parking
Free Wi-Fi
Pet-friendly
£175+
Check availability
The Snug - Chepstow
The Snug
Chepstow, WLS, United Kingdom
8.0Very Good(2)
Free Wi-Fi
Pet-friendly
£142+
Check availability
Welsh Apple Barn - Chepstow
Welsh Apple Barn
Chepstow, WLS, United Kingdom
9.4Wonderful(53)
Parking
Free Wi-Fi
£136+
Check availability
Wye View - Chepstow
Wye View
Chepstow, WLS, United Kingdom
9.1Wonderful(136)
Parking
Free Wi-Fi
£94+
Check availability
Gardener's Cottage - Chepstow
Gardener's Cottage
Chepstow, WLS, United Kingdom
9.6Wonderful(25)
Parking
Free Wi-Fi
£210+
Check availability
The Stables Trap Farm - Chepstow
The Stables Trap Farm
Chepstow, WLS, United Kingdom
8.3Very Good(27)
Parking
Free Wi-Fi
£204+
Check availability
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£0 - £336£336 - £670£670 - £1,006£1,006 - £1,341£1,341+ per night

Property Types

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Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

April

High season

February

Average price (weeknight)

£99

Average price (weekend night)

£102
Cheapest month to stay with an average 21% drop in price.
Most expensive month to stay with an average 44% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Chepstow holiday rental deals

  • Holiday rentals in Chepstow are around 51% more expensive than hotels on average. Search here to compare prices for all accommodation types in Chepstow.
  • The best holiday rental properties in Chepstow are Modern, Two Double Bedroom House With Fr (9.8, 33 reviews), Wye Valley Countryside Retreat (9.7, 86), and Gardener's Cottage (9.6, 25), based on ratings and reviews from real travellers.
  • If you’re looking for a cheap holiday rental in Chepstow, you should consider visiting during the low season. The cheapest holiday homes in Chepstow can be found in April and July.
  • The cheapest night for renting a holiday home in Chepstow is Thursday. In contrast, the most expensive is Friday.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Chepstow for 2 days.
See more tips

FAQs when booking a holiday home in Chepstow

  • What types of holiday rentals are available in Chepstow?

    There are loads of different property types that you can make your holiday home in Chepstow. You’ll find apartments, campgrounds, castles, cottages, houses, campsites, homestays and luxury tents.

  • What are some of the most-loved holiday rentals available in Chepstow?

    If you’re looking for something special, the holiday rental most loved by KAYAK users is Wye View.

  • What are the most popular Chepstow holiday rentals for a large group?

    If you’re a large group then you’ll need plenty of space. The highest rated holiday home that can sleep 6 people or more by KAYAK users is Wye View.

  • Are there any pet-friendly holiday rentals in Chepstow?

    There are a number of dog and pet-friendly Chepstow holiday rentals, with around 17% allowing you to bring your pet along with you.

  • How can I find holiday rentals near me in Chepstow?

    Take a look at our holiday rentals map to find the best holiday rental homes near you.

See more FAQs

Where to stay in Chepstow?

Our map will help you find the perfect place to stay in Chepstow by showing you the exact location of each holiday rental.

Everything you need to know for your stay in Chepstow

Chepstow holiday rental deals. Search for holiday homes, apartments, condos, cabins, cottages, villas and more in Chepstow. Find cheap holiday homes to rent in Chepstow. KAYAK searches hundreds of travel sites to help you find and book a holiday rental in Chepstow that suits you best.

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