Search
Best rentals
Tips
FAQs
Map

Chepstow vacation rentals

KAYAK searches hundreds of travel sites at once for vacation home deals in Chepstow

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Best Chepstow vacation rentals

Most recommended vacation rentals in Chepstow

Show all
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
$229+
Check availability
Broadrock Accommodation - Clock Cottage - Chepstow - Bedroom
Broadrock Accommodation - Clock Cottage
Chepstow, WLS, United Kingdom
8.8Very good(71)
Parking
Free Wi-Fi
$219+
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
$219+
Check availability
Cider Mill Lodge - Hw7420 - Chepstow - Pool
Cider Mill Lodge - Hw7420
Chepstow, WLS, United Kingdom
9.1Wonderful(8)
Free Wi-Fi
Spa
$616+
Check availability
The Honey Pot - Chepstow - Bedroom
The Honey Pot
Chepstow, WLS, United Kingdom
10Wonderful(8)
Free Wi-Fi
Spa
$318+
Check availability
Welsh Marches - Blorenge - Chepstow - Living room
Welsh Marches - Blorenge
Chepstow, WLS, United Kingdom
Free Wi-Fi
$159+
Check availability
Welsh Marches - Skirrid - Chepstow - Living room
Welsh Marches - Skirrid
Chepstow, WLS, United Kingdom
Free Wi-Fi
$188+
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
$94+
Check availability
Wye Valley Countryside Retreat - Chepstow - Dining room
Wye Valley Countryside Retreat
Chepstow, WLS, United Kingdom
9.7Wonderful(86)
$125+
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
$252+
Check availability
Carpenters Cottages - Chepstow
Carpenters Cottages
Chepstow, WLS, United Kingdom
8.1Very good(152)
Parking
Free Wi-Fi
Pet friendly
$234+
Check availability
The Snug - Chepstow
The Snug
Chepstow, WLS, United Kingdom
8.0Very good(2)
Free Wi-Fi
Pet friendly
$190+
Check availability
Welsh Apple Barn - Chepstow
Welsh Apple Barn
Chepstow, WLS, United Kingdom
9.4Wonderful(53)
Parking
Free Wi-Fi
$182+
Check availability
Wye View - Chepstow
Wye View
Chepstow, WLS, United Kingdom
9.1Wonderful(136)
Parking
Free Wi-Fi
$126+
Check availability
Gardener's Cottage - Chepstow
Gardener's Cottage
Chepstow, WLS, United Kingdom
9.6Wonderful(25)
Parking
Free Wi-Fi
$281+
Check availability
The Stables Trap Farm - Chepstow
The Stables Trap Farm
Chepstow, WLS, United Kingdom
8.3Very good(27)
Parking
Free Wi-Fi
$274+
Check availability
Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

$0 - $450$450 - $899$899 - $1,349$1,349 - $1,798$1,798+ per night

Property Types

ApartmentCottageHomestayHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

KAYAK's top tips for finding Chepstow vacation rental deals

  • Vacation rentals in Chepstow are around 52% more expensive than hotels on average. Search here to compare prices for all accommodation types in Chepstow.
  • The best vacation 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 travelers.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Chepstow for 2 days.

FAQs when booking a vacation home in Chepstow

  • What types of vacation rentals are available in Chepstow?

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

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

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

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

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

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 vacation rental.

Everything you need to know for your stay in Chepstow

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

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.