
Holiday rentals in Chepstow
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chepstow
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Chepstow holiday rentals
Other great holiday rentals in Chepstow
Top guest favourite

Home
5 out of 5 average rating, 14 reviewsOlive Barn at Cwmhir Court
ElizabethRating, 5 stars1 week ago
Great house, perfect for our group. Rebecca was a great host.
Top guest favourite

Farm stay
4.95 out of 5 average rating, 21 reviewsCotswolds Farm - Beautiful Hay Barn conversion
EllieRating, 5 stars1 month ago
We had a lovely stay for a few nights. It wasn't great weather, so the little games room on site was very useful to entertain the kids. Great, quiet, countryside location but not too far from pubs etc. The barn had everything we needed to make our stay enjoyable.
Guest favourite

Home
4.96 out of 5 average rating, 73 reviewsCosy House on the Edge of Brecon Beacons
CharleyRating, 5 stars5 days ago
We booked this for two of our gents working in the area. No complaints! Lovely home, easy check in & friendly hosts.
Superhost

Barn
4.87 out of 5 average rating, 439 reviewsThe Beach Barn
TomRating, 5 stars1 week ago
Myself and my partner stayed two nights, the location is perfect. Less than 5 meters from the front gate to the beach. Less than 3 minute walk through to a local pub/restaurant. The inside of the property is exactly as described. Overall we had a lovely time and would come back again. Thank you Austin.
Guest favourite

Cabin
4.91 out of 5 average rating, 44 reviewsWoodsman Cabin - Private Hot Tub & Panoramic Views
MeganRating, 5 stars2 weeks ago
Most incredible stay ever! We will be booking to come here every year from now on!! Couldn’t ask for a more beautiful place to stay
Superhost

Cottage
5 out of 5 average rating, 5 reviewsLovely Cottage on the edge of a small farm
SallyRating, 5 stars3 months ago
It was the perfect cosy cottage to spend Christmas together as a family gathering from Dorset, Gloucester and locally. Thank you!
Superhost

Flat
4.8 out of 5 average rating, 10 reviewsQuiet Eco Home - Parking - Wi-Fi - 3BR, Sleeps 8
BenRating, 5 stars4 weeks ago
We needed a place to stay last minute as having renovations in our home. The flexibility and response to this was great. The house was comfortable, warm and clean. Amos and Don were responsive in their communication. We felt at home and enjoyed our stay. 👍🏻
Guest favourite

Home
4.95 out of 5 average rating, 21 reviewsThe Warm Hearth: The Stables
SophieRating, 5 stars6 months ago
Amazing place for children, the outdoor space is magical and so much for them to do. Beautiful surroundings and the hosts were lovely. A few things in the house were a bit wonky but overall a great stay.
Quick stats about holiday rentals in Chepstow
Total rentals
30 properties
Nightly prices starting at
£8 before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
30 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Destinations to explore
- Bristol Holiday rentals
- Cotswolds Holiday rentals
- Cotswold District Holiday rentals
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- Brecon Beacons national park
- Principality Stadium
- Cardiff Castle
- Cheltenham Racecourse
- Stonehenge
- Sudeley Castle
- Bike Park Wales
- Puzzlewood
- Bute Park
- Kilve Beach
- Royal Porthcawl Golf Club
- Caerphilly Castle
- Porthcawl Rest Bay Beach
- Cabot Tower
- Bowood House and Gardens
- Astley Vineyard
- Lacock Abbey
- Zip World Tower
- Dyrham Park
- Manor House Golf Club
- Bryn Meadows Golf Hotel & Spa
- Aberavon Beach
- National Showcaves Centre for Wales
- Porthcawl Sea Front