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Villas in Chepstow and Houses - Holiday Lettings - Holiday Rentals Chepstow

554 Holiday homes

Chepstow holiday b&b rental

Chepstow b&b

2 bedrooms • 4 bathrooms • sleeps 4

from £172 / night

£1,145 / week

1 / 26

Holiday cottage in Brockweir

Brockweir cottage

1 bedroom • 1 bathroom • sleeps 2

from £86 / night

£516 / week

1 / 24

Itton holiday barn let

Itton barn

1 bedroom • 1 bathroom • sleeps 2

“Felt like home” If you are looking for a retreat from the hussle and bussle of every day life then Dolly's Barn is the place to stay. Warm, cosy and full of character. Stunning views and beautiful scenery. The owner Helen was very welcoming and made me feel at home. There were so many great walks nearby for me and my dogs. After being out and about during the day, curling up in front of the wood burning stove of an evening was such a treat. I had such an amazing week that I have already booked again for next year!!! I would highly recommend Dolly's Barn to other people.

from £115 / night

£504 - £550 / week

1 / 10

Itton holiday cottage rental

Itton cottage

2 bedrooms • 1 bathroom • sleeps 4

“Amazing cottage with stunning garden and views to die for” Helen was the perfect 'host' she was there when we needed any information and was discreet when we were happy to stay 'at home'. The cottage was incredibly well equipped and cosy. The furnishings were wonderful and reminded us of family homes, a mixture of interesting and well loved pieces. A car would be required to stay at the cottage as it is set in countryside but parking is off road. Our two dogs, Ellie and Barney were made especially welcome which made the whole experience enjoyable without being anxious about them. The location of the property is close to some fantastic walks and Helen gave us easy directions to them. We couldn't fault the whole experience (apart from we could have had better weather) and look forward to booking again for next year.

from £132 / night

£619 - £682 / week

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Chepstow holiday cottage rental

Chepstow cottage

2 bedrooms • 1 bathroom • sleeps 4

“Amazing cottage with stunning garden and views to die for” Helen was the perfect 'host' she was there when we needed any information and was discreet when we were happy to stay 'at home'. The cottage was incredibly well equipped and cosy. The furnishings were wonderful and reminded us of family homes, a mixture of interesting and well loved pieces. A car would be required to stay at the cottage as it is set in countryside but parking is off road. Our two dogs, Ellie and Barney were made especially welcome which made the whole experience enjoyable without being anxious about them. The location of the property is close to some fantastic walks and Helen gave us easy directions to them. We couldn't fault the whole experience (apart from we could have had better weather) and look forward to booking again for next year.

from £126 / night

£642 / week

1 / 17

Holiday home in Chepstow

Chepstow house

2 bedrooms • 1 bathroom • sleeps 3

from £201 / night

£652 - £1,474 / week

1 / 22

Holiday home in Chepstow

Chepstow house

3 bedrooms • 3 bathrooms • sleeps 9

from £567 / night

£3,968 / week

1 / 35

Holiday tower with golf nearby in Mathern

Mathern tower

1 bedroom • 1 bathroom • sleeps 2

from £213 / night

£1,208 / week

1 / 17

Home rental in Chepstow

Chepstow house

1 bedroom • 1 bathroom • sleeps 2

“Felt like home” If you are looking for a retreat from the hussle and bussle of every day life then Dolly's Barn is the place to stay. Warm, cosy and full of character. Stunning views and beautiful scenery. The owner Helen was very welcoming and made me feel at home. There were so many great walks nearby for me and my dogs. After being out and about during the day, curling up in front of the wood burning stove of an evening was such a treat. I had such an amazing week that I have already booked again for next year!!! I would highly recommend Dolly's Barn to other people.

from £115 / night

£516 / week

1 / 8

Holiday lodge in Chepstow

Chepstow lodge

1 bedroom • 1 bathroom • sleeps 2

from £98 / night

£676 / week

1 / 4

Great rentals within 20 miles that match your search

Holiday barn with golf nearby in Blakeney, Gloucestershire

Blakeney, Gloucestershire barn

1 bedroom • 1 bathroom • sleeps 2

from £126 / night

£1,088 / week

1 / 41

Holiday cottage rental

Blakeney, Gloucestershire cottage

3 bedrooms • 1 bathroom • sleeps 5

from £108 / night

£573 / week

1 / 13

Holiday cottage in Staunton

Staunton cottage

2 bedrooms • 2 bathrooms • sleeps 4

from £98 / night

£682 / week

1 / 21

Holiday cottage in Coed-Y-Paen

Coed-Y-Paen cottage

2 bedrooms • 1 bathroom • sleeps 4

from £109 / night

£745 / week

1 / 20

Holiday b&b in Redbrook

Redbrook b&b

3 bedrooms • 1 bathroom • sleeps 2

from £109 / night

£687 / week

1 / 13

Holiday cottage in Blakeney

Blakeney cottage

2 bedrooms • 1 bathroom • sleeps 4

from £138 / night

£1,088 / week

1 / 33

Nailsworth holiday barn rental

Nailsworth barn

2 bedrooms • 1 bathroom • sleeps 4

from £107 / night

£561 - £785 / week

1 / 32

Tetbury holiday home rental

Tetbury house

2 bedrooms • 1 bathroom • sleeps 4

from £161 / night

£802 / week

1 / 17

Farmhouse rental in Tetbury

Tetbury farmhouse

3 bedrooms • 1 bathroom • sleeps 5

from £184 / night

£974 / week

1 / 30

Cottage rental in Tetbury

Tetbury cottage

1 bedroom • 1 bathroom • sleeps 2

from £172 / night

£745 / week

1 / 18

Holiday barn in Tetbury

Tetbury barn

1 bedroom • 1 bathroom • sleeps 2

from £138 / night

£745 / week

1 / 29

Dyrham holiday home rental

Dyrham house

1 bedroom • 1 bathroom • sleeps 2

from £108 / night

£322 - £857 / week

1 / 9

Holiday cottage in Longhope

Longhope cottage

2 bedrooms • 2 bathrooms • sleeps 5

from £201 / night

£1,403 / week

1 / 16

Lydbrook holiday home let

Lydbrook house

5 bedrooms • 6 bathrooms • sleeps 11

from £739 / night

£5,170 / week

1 / 40

Holiday apartment in Monmouth

Monmouth apartment

1 bedroom • 1 bathroom • sleeps 4

from £58 / night

£401 - £642 / week

1 / 24

Bristol holiday home rental

Bristol house

4 bedrooms • 2 bathrooms • sleeps 7

from £201 / night

£1,374 / week

1 / 6

Holiday home in Symonds Yat

Symonds Yat house

2 bedrooms • 1 bathroom • sleeps 4

from £97 / night

£319 - £1,057 / week

1 / 14

Holiday lodge rental

Bristol lodge

1 bedroom • 1 bathroom • sleeps 4

from £86 / night

£481 - £802 / week

1 / 45

Holiday home in Tintern

Tintern house

1 bedroom • 1 bathroom • sleeps 2

from £111 / night

£331 - £858 / week

1 / 24

Holiday b&b in Whitminster

Whitminster b&b

1 bedroom • 1 bathroom • sleeps 2

from £86 / night

£504 / week

1 / 14

Whitchurch holiday home rental

Whitchurch house

8 bedrooms • 8 bathrooms • sleeps 20

from £520 / night

£1,559 - £6,157 / week

1 / 19

Bristol holiday home rental

Bristol house

2 bedrooms • 2 bathrooms • sleeps 5

from £149 / night

£1,042 / week

1 / 15

Clevedon holiday apartment rental

Clevedon apartment

1 bedroom • 1 bathroom • sleeps 2

from £86 / night

£602 / week

1 / 17

Holiday b&b rental

Monmouth b&b

1 bedroom • 1 bathroom • sleeps 2

from £86 / night

£602 / week

1 / 22

Rogerstone holiday cottage rental

Rogerstone cottage

4 bedrooms • 5 bathrooms • sleeps 8

from £126 / night

£745 / week

1 / 33

Mitcheldean holiday cottage rental

Mitcheldean cottage

2 bedrooms • 1 bathroom • sleeps 4

from £161 / night

£1,123 / week

1 / 51

Holiday home in Bitton

Bitton house

1 bedroom • 1 bathroom • sleeps 2

from £87 / night

£296 - £910 / week

1 / 14

Holiday tented camp in Abergavenny

Abergavenny tented camp

3 bedrooms • 2 bathrooms • sleeps 18

from £228 / night

£974 - £10,592 / week

1 / 34

Holiday cottage in Dundry

Dundry cottage

2 bedrooms • 2 bathrooms • sleeps 4

from £192 / night

£687 / week

1 / 43

Holiday cottage in Nailsworth

Nailsworth cottage

2 bedrooms • 1 bathroom • sleeps 4

from £109 / night

£659 / week

1 / 26

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Top Destination reviews

Dolly's Barn with stunning views and green credentials
Dolly's barn

Great accommodation, excellent access and dog managements. Very peaceful. We will return. Situated close to convenient stores /pub and close to nature and great walks. … see more
The Welsh Gatehouse: Decontamination between guests.
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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