List your home
Apply filters
£ to

10 Holiday homes in Chepstow

Reset search

Show results on map

Filter your search

Price per night

£ to

Bedrooms

Location

  • Wales Clear
  • Southern Wales Clear
  • Monmouthshire Clear
  • Chepstow Clear
  • All locations
  • Brockweir (2)
  • Gaerllwyd (2)
  • Llanishen (2)
  • Mathern (2)

more +

less -

Property type

more +

less -

Also consider

Coastal Cottages
222 properties
Pet Friendly Cottages
26,614 properties
Brecon
115 properties
Tenby
115 properties
Conwy
78 properties
Trearddur Bay
75 properties
Llangollen
57 properties
Benllech
49 properties
Harlech
49 properties
Aberdyfi (Aberdovey)
48 properties
Llandudno
47 properties
Freshwater East
45 properties
Criccieth
44 properties
Rhosneigr
44 properties
Dyffryn Ardudwy
40 properties
Machynlleth
40 properties
Abergavenny
39 properties
Solva
39 properties
Aberaeron
38 properties
Llandovery
38 properties

Filters applied: Garden (10)

To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
10 Results  |  
24 Photos

Cottage | 1 Bedroom | sleeps 2

Excellent 5/5 

Short stays welcome

Add to shortlist

from £53 /night

£365 - £420 / week

View

Key info:

  • Nearest beach 90 km
  • Not suitable for children
  • Car essential
  • No pets allowed
  • Private garden
Hillside rural location near Chepstow & Monmouth. Forest of Dean and Wye Valley. Self catering holiday cottage. Birdwatching, badgers activity holidays. Cycling walking kyaking coastal surfing diving rock climbing fishing golf festivals historic castles Offas Dyke Short Breaks min 3 nights on request. Cooking facilities comprise a combination oven/microwave/grill & hob  …see more

19 Photos

Cottage | 2 Bedrooms | sleeps 4

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £65 /night

£450 - £650 / week

View

Key info:

  • Nearest beach 100 km
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Restored characterful cottage in the Wye Valley Area of Outstanding Natural Beauty. Set within extensive woodland only 5 minutes from Tintern and the River Wye. Sleeps 4 in 2 pretty bedrooms. Cosy lounge with wood burner. Fully equipped kitchen with modern appliances. Sunny conservatory. Cottage garden with outdoor seating and barbecue Visit Wales Accredited - 5 Stars  …see more

14 Photos

Cottage | 1 Bedroom | sleeps 2

6 Nights min stay

Add to shortlist

from £40 /night

£275 - £395 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
1 bedroom dog friendly holiday cottage in a peaceful rural location with magnifent views  …see more

Featured properties

17 Photos

Tower | 1 Bedroom | sleeps 2

Excellent 5/5 

1 night min stay

Add to shortlist

from £70 /night

£490 - £721 / week

View

Key info:

  • Not suitable for children
  • Car advised
  • No pets allowed
A luxury award winning period property, built in the time of Edward I, (we think it was built approx 1270). This Grade II* medieval hideaway boasts seven hundred years of history - and with its towers it feels like you are living in a fairytale castle!! The perfect couples retreat, a great base for exploring South Wales! Stay for 1 night or 1 week.  …see more

17 Photos

Cottage | 3 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

Add to shortlist

from £78 /night

£540 - £650 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • Pets welcome
Set in 126 acres of beautiful open meadows, woodland and rolling hills on a working farm, Maes y Gwy Holiday Cottage in Monmouthshire has a hot tub, large play area and games room. Weekly lets from £540 / Short breaks from £190  …see more

20 Photos

House | 9 Bedrooms | sleeps 20

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £1372 /night

£9600 - £9800 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Wyelands House is a large, elegant Regency style villa. The house and spacious grounds are available to rent exclusively for private house parties, corporate entertaining, business meetings, management training, team building weekends and photo shoots.  …see more

31 Photos

House | 2 Bedrooms | sleeps 4

Short stays welcome

Add to shortlist

from £42 /night

£292 - £628 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Sleeping four people in two bedrooms, this quality ground floor apartment is next to the owners country pub/restaurant in the small village of Llanishen, 7 miles from Chepstow.  …see more

31 Photos

House | 2 Bedrooms | sleeps 4

Short stays welcome

Add to shortlist

from £42 /night

£292 - £574 / week

View

Key info:

  • Suitable for children over 5
  • Car advised
  • No pets allowed
  • Private garden
Sleeping four people in two bedrooms, this quality first floor apartment is next to the owners country pub/restaurant in the small village of Llanishen, 7 miles from Chepstow.  …see more

24 Photos

Barn | 2 Bedrooms | sleeps 4

Short stays welcome

Add to shortlist

from £63 /night

£435 - £860 / week

View

Key info:

  • Suitable for children over 5
  • Car advised
  • Pets welcome
  • Private garden
stylish detached barn with private garden and hot tub this newly converted barn is situated in beautiful countryside between the wye valley and the forest of dean overlooking the river severn and just over 2 miles from chepstow adjacent to the a48. Nestling in the southwest corner of gloucestershire with direct access across the owners land there are walks in all directions to explore the area including the offa s dyke path. It is close to wye valley brecon beacons and family attractions in the forest of dean. The national diving and activity centre are also nearby enjoy zip wire rides water walking fly boarding as well as diving for all abilities. An equestrian centre is opposite the house for guests wishing to go horse riding. For those looking for quieter activities take a look at chepstow castle and bridge which sits above the wye or a round of golf at the nearby golf course. Lastly a visit to chepstow would not be complete without a visit to the racecourse home to the welsh national each year. The accommodation all on the ground floor with exposed a frame beams floor to ceiling picture windows and under floor heating throughout offers two bedrooms both with en-suite wet room showers and wc s: 1 zip and link double which can be made into a twin on request and 1 double room. Lounge/kitchen/diner: open plan and well equipped with tv/dvd double sofa bed and wi-fi. Kitchen area: with washing machine dishwasher fridge/freezer electric oven/hob and microwave. Outside: private lawn area with hot tub. Amenities: ample allocated parking for 2 cars. Bed linen towels electric heating and wi-fi included. 2 dogs welcome. Regret no smoking. Location: pubs shops and restaurants in chepstow 2 miles. Farm shop/deli within walking distance. Any property identified with increased accessibility may have different levels of provision it is therefore advisable you contact us before you book to ensure the property meets your specific needs and requirements.  …see more

16 Photos

Cottage | 3 Bedrooms | sleeps 5

Very Good 4.5/5 

1 night min stay

Add to shortlist

from £78 /night

£540 - £650 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • Pets welcome
Maes y Felin is a Holiday Cottage with a hot tub and is located on a working farm set in 126 acres of beautiful open meadows, woodland and rolling hills. There is a large playground and games room. Weekly lets from £540 / Short breaks from £190  …see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page