Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
Start your search
Location
Homes in Chepstow
Check in / Check out
Any week
Guests
Add guests
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Type of place
Show map
Search results; Over 1,000 homes
Over 1,000 homes
Top guest favourite
Guest favourite
Apartment in Chepstow
Luxurious homely and cosy 1st floor apartment.
2 bedrooms
,
·
2 beds
,
·
1 private bathroom
21–26 Sept
21–26 Sept
$954 SGD
$835 SGD
Show price breakdown
for 5 nights
,
·
5.0 out of 5 average rating, 314 reviews
5.0 (314)
Top guest favourite
Guest favourite
Home in Tutshill
A most unusual Manor House
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
7–12 Nov
7–12 Nov
$2,420 SGD
$2,155 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 41 reviews
5.0 (41)
Top guest favourite
Guest favourite
Cottage in Saint Arvans
Cheerful 3 bedroom cottage a walkers Parìdice!
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
7–12 Sept
7–12 Sept
$1,205 SGD
Show price breakdown
for 5 nights
$1,205 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 178 reviews
4.97 (178)
Top guest favourite
Guest favourite
Cottage in Brockweir
3 bedroom, peaceful, secluded, & large garden
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
9–14 Sept
9–14 Sept
$1,963 SGD
$1,733 SGD
Show price breakdown
for 5 nights
Free cancellation
4.99 out of 5 average rating, 287 reviews
4.99 (287)
Top guest favourite
Guest favourite
Home in Tidenham
Country Farmhouse | Hamlet Views & Walks from Door
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
14–20 Sept
14–20 Sept
$4,321 SGD
$3,807 SGD
Show price breakdown
for 6 nights
4.97 out of 5 average rating, 31 reviews
4.97 (31)
Guest favourite
Guest favourite
Home in Devauden
Large Countryside House with Hot Tub, sleeps 17.
7 bedrooms
7 bedrooms
,
·
12 beds
12 beds
,
·
3 bathrooms
3 bathrooms
2–7 Sept
2–7 Sept
$7,555 SGD
Show price breakdown
for 5 nights
$7,555 SGD for 5 nights
5.0 out of 5 average rating, 25 reviews
5.0 (25)
Top guest favourite
Guest favourite
Bus in Llanvair-Discoed
The Bothy Bus
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$992 SGD
$869 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 30 reviews
5.0 (30)
Top guest favourite
Guest favourite
Cottage in Wales
Birdsong Cottage
2 bedrooms
2 bedrooms
,
·
2 king beds
2 king beds
,
·
2 bathrooms
2 bathrooms
4–9 Sept
4–9 Sept
$2,063 SGD
$1,807 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 84 reviews
5.0 (84)
Top guest favourite
Guest favourite
Barn in Monmouthshire
Craigo Barn Nature Retreat
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$1,291 SGD
Show price breakdown
for 5 nights
$1,291 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 15 reviews
4.93 (15)
Top guest favourite
Guest favourite
Guest house in Monmouthshire
The coachouse.
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2.5 bathrooms
2.5 bathrooms
6–11 Sept
6–11 Sept
$1,308 SGD
$1,150 SGD
Show price breakdown
for 5 nights
Free cancellation
4.96 out of 5 average rating, 180 reviews
4.96 (180)
Top guest favourite
Guest favourite
Home in Trellech
The Lodge
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
21–26 Sept
21–26 Sept
$1,446 SGD
$1,274 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 56 reviews
5.0 (56)
Top guest favourite
Guest favourite
Flat in Gloucestershire
Idyllic Country Retreat in the Forest of Dean
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
21–26 Sept
21–26 Sept
$860 SGD
$755 SGD
Show price breakdown
for 5 nights
4.99 out of 5 average rating, 140 reviews
4.99 (140)
Top guest favourite
Guest favourite
Cottage in Chepstow
Pineapple Cottage - Chepstow Town Centre (Wales)
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
$924 SGD
$818 SGD
Show price breakdown
for 5 nights
Free cancellation
4.88 out of 5 average rating, 548 reviews
4.88 (548)
Guest favourite
Guest favourite
Farm stay in Chepstow
Sugar Loaf - @ Welsh Marches
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
2–7 Sept
2–7 Sept
$2,582 SGD
Show price breakdown
for 5 nights
$2,582 SGD for 5 nights
4.93 out of 5 average rating, 58 reviews
4.93 (58)
Top guest favourite
Guest favourite
Cottage in Chepstow
Character cottage, stroll to town, Wye Valley base
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
18–23 Nov
18–23 Nov
$2,277 SGD
Show price breakdown
for 5 nights
$2,277 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 114 reviews
4.97 (114)
Top guest favourite
Guest favourite
Apartment in Monmouthshire
Castle House Apartment 3 Georgian town house
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
2–7 Sept
2–7 Sept
$1,286 SGD
$1,131 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 77 reviews
4.95 (77)
Top guest favourite
Guest favourite
Cabin in Gloucestershire
Coppice Cabin - Private Hot Tub & Panoramic Views
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
21–27 Sept
21–27 Sept
$2,296 SGD
$2,066 SGD
Show price breakdown
for 6 nights
Extended stay discount
4.99 out of 5 average rating, 86 reviews
4.99 (86)
Top guest favourite
Guest favourite
Room in Pwllmeyric
King size room in quiet village location
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
17–22 Sept
17–22 Sept
$649 SGD
Show price breakdown
for 5 nights
$649 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 87 reviews
4.98 (87)
Top guest favourite
Guest favourite
Rooms in Portskewett
Converted Forge in the centre of a village.
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Nov
1–6 Nov
$682 SGD
Show price breakdown
for 5 nights
$682 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 294 reviews
4.98 (294)
1
2
3
4
…
15