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688 Holiday homes

(30) Excellent 

10

Itton holiday barn let

Chepstow / Itton

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly
  • Pet friendly

from £98 / night

£418 - £498 / week

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from £98 / night

(61) Excellent 

11

Itton holiday cottage rental

Chepstow / Itton

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Pet friendly

from £98 / night

£470 - £613 / week

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from £98 / night

(18) Excellent 

24

Holiday cottage in Brockweir

Chepstow / Brockweir

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 90 km
  • Private garden

from £81 / night

£430 - £510 / week

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Responds fast!
avg. 1 hour 57 minutes

from £81 / night

35

Holiday home in Chepstow

Monmouthshire / Chepstow

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £401 / night

£2,806 / week

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Responds fast!
avg. 44 minutes

from £401 / night

(16) Very Good 

19

Holiday cottage in Brockweir

Chepstow / Brockweir

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 100 km
  • Child friendly
  • Pet friendly

from £84 / night

£556 - £829 / week

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Responds fast!
avg. 3 hours 27 minutes

from £84 / night

(2) Very Good 

19

Chepstow holiday home rental

Monmouthshire / Chepstow

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
  • Car not necessary

from £287 / night

£1,718 - £2,519 / week

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from £287 / night

(70) Excellent 

17

Holiday tower with golf nearby in Mathern

Chepstow / Mathern

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies

from £228 / night

£836 / week

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Responds fast!
avg. 17 minutes

from £228 / night

5

Chepstow holiday log cabin rental

Monmouthshire / Chepstow

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Nearest beach 50 km
  • Car not necessary
  • Air conditioning

from £103 / night

£722 / week

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from £103 / night

(58) Excellent 

17

Chepstow holiday cottage rental

Monmouthshire / Chepstow

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask owner if suitable for children
  • Pet friendly

from £109 / night

£453 - £613 / week

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from £109 / night

31

Chepstow holiday home rental

Monmouthshire / Chepstow

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Private garden

from £62 / night

£1,232 / week

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from £62 / night

26

Chepstow holiday b&b rental

Monmouthshire / Chepstow

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

from £172 / night

£1,145 / week

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from £172 / night

(23) Excellent 

8

Home rental in Chepstow

Monmouthshire / Chepstow

1 2 6 nights min

  • 1 bedroom
  • sleeps 2
  • 6 nights min
  • Child friendly
  • Pet friendly

from £103 / night

£447 / week

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from £103 / night

Great rentals within 20 miles that match your search

Distance approx 18.07 miles from Chepstow

15

Holiday lodge letting

Gloucestershire / Longhope

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Pet friendly

from £144 / night

£573 / week

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from £144 / night

Distance approx 17.37 miles from Chepstow

(6) Excellent 

7

Nympsfield holiday barn rental

Gloucestershire / Nympsfield

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Pet friendly

from £81 / night

£458 - £705 / week

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from £81 / night

Distance approx 18.07 miles from Chepstow

(29) Excellent 

Certificate of Excellence

24

Holiday cottage in Longhope

Gloucestershire / Longhope

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 67 km
  • Child friendly
  • Pet friendly

Certificate of Excellence

from £172 / night

£567 - £1,025 / week

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from £172 / night

Distance approx 19.79 miles from Chepstow

(2) Excellent 

19

Cottage rental in Bridstow

Ross-on-Wye / Bridstow

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min

from £69 / night

£315 / week

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from £69 / night

Distance approx 10.19 miles from Chepstow

(26) Very Good 

20

Holiday cottage in Lydney

Forest of Dean / Lydney

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 50 km
  • Child friendly
  • Private garden

from £269 / night

£1,068 / week

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Responds fast!
avg. 1 hour 43 minutes

from £269 / night

Distance approx 19.47 miles from Chepstow

(24) Excellent 

10

Abergavenny holiday townhouse rental

Monmouthshire / Abergavenny

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Child friendly
  • Private garden

from £103 / night

£682 / week

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from £103 / night

Distance approx 11.78 miles from Chepstow

(34) Excellent 

23

Holiday barn in Wotton-under-Edge

Wotton-under-Edge / Huntingford, Gloucestershire

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly
  • Pet friendly

from £63 / night

£413 - £630 / week

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from £63 / night

Distance approx 16.7 miles from Chepstow

(78) Excellent 

Certificate of Excellence

21

Apartment rental in Ross-on-Wye

Herefordshire / Ross-on-Wye

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Private garden

Certificate of Excellence

from £92 / night

£390 / week

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Responds fast!
avg. 1 hour 32 minutes

from £92 / night

Distance approx 11.62 miles from Chepstow

13

Holiday shepherds hut rental

Forest of Dean / Blakeney, Gloucestershire

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 70 km
  • Child friendly
  • Pet friendly

from £86 / night

£602 / week

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from £86 / night

Distance approx 17.9 miles from Chepstow

(18) Very Good 

11

Leighterton holiday barn rental

Malmesbury / Leighterton

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Private garden

from £109 / night

£487 - £567 / week

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Responds fast!
avg. 2 hours 46 minutes

from £109 / night

Distance approx 13.23 miles from Chepstow

(42) Excellent 

Certificate of Excellence

20

Holiday lodge with golf nearby in Wotton-under-Edge

Stroud District / Wotton-under-Edge

7 20 2 nights min

  • 7 bedrooms
  • sleeps 20
  • 2 nights min
  • Nearest beach 60 km
  • Child friendly
  • Pet friendly

Certificate of Excellence

from £458 / night

£2,290 - £5,496 / week

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Responds fast!
avg. 2 hours 21 minutes

from £458 / night

Distance approx 16.12 miles from Chepstow

5

Holiday b&b in Whitchurch

Ross-on-Wye / Whitchurch

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden

from £58 / night

£401 / week

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from £58 / night

Distance approx 16.88 miles from Chepstow

(1) Excellent 

27

Tetbury holiday cottage rental

Cotswolds / Tetbury

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

from £132 / night

£516 - £899 / week

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from £132 / night

Distance approx 8.36 miles from Chepstow

(1) Excellent 

4

B&b rental in Bristol

England / Bristol

1 1 1 night min

  • 1 bedroom
  • sleeps 1
  • 1 night min
  • Child friendly

from £40 / night

£281 / week

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from £40 / night

Distance approx 16.92 miles from Chepstow

(1) Very Good 

28

Tetbury holiday home rental

Cotswolds / Tetbury

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Child friendly
  • Ask about pets
  • Private garden

from £201 / night

£974 / week

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from £201 / night

Distance approx 12.24 miles from Chepstow

(4) Excellent 

6

Holiday cottage in Caerleon

Newport / Caerleon

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £138 / night

£544 / week

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Responds fast!
avg. 3 hours 41 minutes

from £138 / night

Distance approx 12.09 miles from Chepstow

13

Holiday tented camp rental

Coleford / Newland

3 20 3 nights min

  • 3 bedrooms
  • sleeps 20
  • 3 nights min
  • Child friendly

from £752 / night

£5,258 / week

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from £752 / night

Distance approx 10.57 miles from Chepstow Show on Map

(1) Excellent 

12

Holiday apartment in Usk

Monmouthshire / Usk

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child friendly

from £69 / night

£481 / week

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from £69 / night

Distance approx 15.14 miles from Chepstow

5

Holiday b&b in Littledean

Forest of Dean / Littledean

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £115 / night

£802 / week

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from £115 / night

Distance approx 9.68 miles from Chepstow Show on Map

10

Apartment rental in Llandenny

Monmouthshire / Llandenny

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min

from £172 / night

£1,203 / week

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from £172 / night

Distance approx 9.68 miles from Chepstow Show on Map

12

Apartment rental in Llandenny

Monmouthshire / Llandenny

2 3 2 nights min

  • 2 bedrooms
  • sleeps 3
  • 2 nights min
  • Child friendly

from £138 / night

£962 / week

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from £138 / night

Distance approx 9.68 miles from Chepstow Show on Map

6

Apartment rental in Llandenny

Monmouthshire / Llandenny

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child friendly

from £144 / night

£1,002 / week

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from £144 / night

Distance approx 18.64 miles from Chepstow

16

Holiday home in Llantilio Pertholey

Monmouthshire / Llantilio Pertholey

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Pet friendly
  • Private garden

from £38 / night

£266 / week

Enquire View

from £38 / night

Distance approx 15.03 miles from Chepstow

19

Whitchurch holiday home rental

Ross-on-Wye / Whitchurch

8 20 1 night min

  • 8 bedrooms
  • sleeps 20
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £183 / night

£1,281 / week

Enquire View

from £183 / night

Distance approx 11.98 miles from Chepstow

11

Holiday cottage in Blakeney

Forest of Dean / Blakeney

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

from £98 / night

£682 - £831 / week

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from £98 / night

Distance approx 12.92 miles from Chepstow

21

Bristol holiday apartment rental

England / Bristol

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Ask owner if suitable for children

from £119 / night

£834 / week

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from £119 / night

Distance approx 12.42 miles from Chepstow

6

Bristol holiday home rental

England / Bristol

3 12 1 night min

  • 3 bedrooms
  • sleeps 12
  • 1 night min

from £40 / night

£281 / week

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from £40 / night

Distance approx 19.32 miles from Chepstow

13

Lea holiday cottage rental

Ross-on-Wye / Lea

2 3 min stay varies

  • 2 bedrooms
  • sleeps 3
  • min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

from £123 / night

£739 - £1,096 / week

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from £123 / night

Top Destination reviews

Spring Cottage
A beautiful find

I don't normally write reviews but felt I needed to. My friend and I booked this cottage as our yearly pre-summer holiday break...the wind down before having the kids at home for 6 weeks. We normally do Clovelly which we adore but I felt like a change. The drive to the cottage instantly relaxed you, down a lane that only fits one car but with properties and views so quaint I felt miles from all the world's stresses. We arrived at the gorgeous cottage and I have to say the photos on here are true to size. It was lovely to arrive to real coffee, fresh eggs and homemade bread. The little cottage garden with the willow Tree had a lovely bistro set underneath, and eating breakfast there in the mornings was a dream. It was so quiet...Yes the owners live in the house opposite, however you don't notice it and it's not overlooking you or intrusive. The walks were stunning. We walked up the steep hill through the woods, back along the river, through fields with horses...the amazing walk to tintern abbey down the old railway track, along the river, a pint in the local pub...it was truly a relaxing find a million miles from anywhere.... We both felt it was great value and beautifully done. Only wish we had longer to do more of the walks on offer.see more
Maes-y-Felin Monmouthshire farmstay cottage- 46322
Great place

I just needed somewhere to stay that was convenient for events in Abergavenny and Blaenavon but not too remote. This cottage was perfect for this. The facilities were great and we made full use of them. I cannot fault the cottage and we were made most welcome. I would love to go back and would recommend it to anyonesee more
The Welsh Gatehouse (Book for more nights and the price will decrease)
Magic. We just loved it....

We had a fantastic and really memorable stay. To say that it is unique is just not doing it justice, as it is sooooo romantic and so cosy that we would love to be there every weekend. We had intended to do lot's of sightseeing, but we found it hard to tear ourselves away from the place. The stairs up are different, but what do you expect in what is a property / castle built over 500 years ago! Highly recommend visiting Tintern Abbey, the other side of Chepstow.see more
Oakgrove Cottage
Relaxing oasis!

Just what we needed, we have a 3 month old baby and just wanted somewhere we could totally chill without worrying about neighbours etc if he cried which obviously they do! We had everything we needed in the property, when we arrived Gina met us and showed us how everything worked and recommended a few places to go and eat. The accomodation was clean and well looked after and we felt relaxed as soon as we unpacked. We had a couple of days just relaxing and sunbathing but we ate out every night at the local pubs and everyone was so friendly especially at the Anchor the food was amazing too. If you want to do lots there are plenty of places to visit and lots of walks but if you just want a lazy time like us then the accomodation suits that too as there is a lovely patio area where you can just relax and at nightime watch the local wildlife, we had a badger come right up to the window. Overall a total oasis from the busy city!see more

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