Chepstow Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

675 Houses

(58) Excellent 

17

Pet friendly Clares Holiday Cottage with stunning views & green credentials

Monmouthshire / Chepstow

Chepstow cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children
  • Pet Friendly
“Great holiday in a fantastic cottage” Clare's cottage is just simply fantastic. We had a very warm welcome from Helen the owner when we arrived. Who gave us some great advice on the best walks nearby and details of all the local amenities. The cottag
…see more

Price per night from

$87

Price per night from

$87

26

Ty'r Castell Band B, Chepstow, Monmouthshire

Monmouthshire / Chepstow

Chepstow b and b

2 4 1 night min

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

Price per night from

$189

Price per night from

$189

31

No8 CHEPSTOW, luxury interior, en-suite bedrooms, cinema room, Ref 977746

Monmouthshire / Chepstow

Chepstow house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Private garden

Price per night from

$82

Price per night from

$82

(23) Excellent 

8

Dog friendly Dolly's Barn Barn with stunning views & green credentials

Monmouthshire / Chepstow

Chepstow house

1 2 6 nights min

  • 1 bedroom
  • sleeps 2
  • 6 nights min
  • Child Friendly
  • Pet Friendly
“Fantastic cottage, great little bolt-hole, excellent walking cou” Cottage is superbly equipped with all you need for cosy dinners in. Great location for a whole range of walks. Very comfortable, comes highly recommended.
…see more

Price per night from

$114

Price per night from

$114

(30) Excellent 

10

Dolly's Barn with stunning views and green credentials

Chepstow / Itton

Itton barn

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Pet Friendly
“Fantastic cottage, great little bolt-hole, excellent walking cou” Cottage is superbly equipped with all you need for cosy dinners in. Great location for a whole range of walks. Very comfortable, comes highly recommended.
…see more

Price per night from

$76

Price per night from

$76

(61) Excellent 

11

Clare's Cottage home from home in the country

Chepstow / Itton

Itton cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Pet Friendly
“Great holiday in a fantastic cottage” Clare's cottage is just simply fantastic. We had a very warm welcome from Helen the owner when we arrived. Who gave us some great advice on the best walks nearby and details of all the local amenities. The cottag
…see more

Price per night from

$86

Price per night from

$86

(18) Excellent 

24

Oakgrove Cottage

Chepstow / Brockweir

Brockweir cottage

1 2 min stay varies

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

Price per night from

$75

Responds fast!
avg. 1 hour 57 minutes

Price per night from

$75

(69) Excellent 

17

The Welsh Gatehouse (Book for more nights and the price will decrease)

Chepstow / Mathern

Mathern tower

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min

Price per night from

$151

Responds fast!
avg. 17 minutes

Price per night from

$151

(2) Very Good 

19

BroadRock holiday let

Monmouthshire / Chepstow

Chepstow house

3 6 3 nights min

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

Price per night from

$315

Price per night from

$315

(16) Very Good 

19

Spring Cottage

Chepstow / Brockweir

Brockweir cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 100 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$91

Responds fast!
avg. 3 hours 14 minutes

Price per night from

$91

5

Bunce’s Balter B&B

Monmouthshire / Chepstow

Chepstow log cabin

1 3 1 night min

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

Price per night from

$114

Price per night from

$114

Great rentals within 20 miles that match your search

Distance approx 12.64 km from Chepstow

(10) Excellent 

7

ARLES BARN, WiFi, patio with furniture, on the edge of the Forest of Dean, Ref 9

Coleford / Christchurch

Christchurch house

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Pet Friendly
  • Private garden

Price per night from

$51

Price per night from

$51

Distance approx 16.1 km from Chepstow

(3) Very Good 

19

THE STABLE, barn conversion, garden, river fishing available in Marstow, Ref 532

Ross-on-Wye / Goodrich

Goodrich house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$57

Price per night from

$57

Distance approx 9.82 km from Chepstow

16

SQUIRREL LODGE AT WOODLANDS VIEW, all ground floor, lawned garden with patio, Wi

Forest of Dean / Coleford

Coleford house

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Child Friendly
  • Private garden

Price per night from

$58

Price per night from

$58

Distance approx 18.37 km from Chepstow

(7) Very Good 

6

THE BYRE, romantic, luxury holiday cottage, with a garden in Llanddewi Skirrid,

Monmouthshire / Llanvetherine

Llanvetherine house

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Child Friendly
“a quiet romantic luxury cottage on a quiet farm!” Excellent cottage , very well stocked for 2 people. Very comfy and warm! Would be more tricky for 2 couples as bathroom,, loo an en suite to main bedroom. family very welcoming. Even the peacock dis
…see more

Price per night from

$53

Price per night from

$53

Distance approx 16.54 km from Chepstow

(11) Excellent 

9

BROOKBANK FOLLY, romantic, character holiday cottage, with a garden in Mitchelde

Forest of Dean / Mitcheldean

Mitcheldean house

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
“The most relaxing stay we have had at a cottage.” We chose this cottage for its quirkiness and also because of other very positive reviews.We loved every minute of our stay and could have stayed another week.Plenty to do in the daytime.We visited cave
…see more

Price per night from

$56

Price per night from

$56

Distance approx 13.03 km from Chepstow

(7) Very Good 

18

Felix Lodge Apartments, Bijou 1 Bed with Kitchen & Sky TV, Near City Centre

England / Bristol

Bristol apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Nearest beach 56 mi
  • Child Friendly
  • Car not necessary

Price per night from

$97

Responds fast!
avg. 2 hours 18 minutes

Price per night from

$97

Distance approx 11.45 km from Chepstow

11

KYMIN VIEW, close to amenities, enclosed lawned garden, WiFi, Monmouth, Ref 9335

Monmouthshire / Monmouth

Monmouth house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Private garden

Price per night from

$55

Price per night from

$55

Distance approx 13.44 km from Chepstow

(30) Excellent 

18

CHIPPING HOUSE, family-friendly, luxury, hot tub, with a garden in Wotton-under-

Stroud District / Wotton-under-Edge

Wotton-under-Edge house

6 16 3 nights min

  • 6 bedrooms
  • sleeps 16
  • 3 nights min
  • Child Friendly
  • Private garden
“Excellent place for a 50th birthday” 10 of us went to Chipping House to celebrate two 50th birthdays. The house was ideal for this purpose - lots of room, masses of crockery, glasses, books, games etc, an excellent village location in a lovely part of
…see more

Price per night from

$339

Price per night from

$339

Distance approx 17.67 km from Chepstow

(28) Very Good 

21

INGLESIDE, family friendly, character holiday cottage, with a garden in Adsett,

Forest of Dean / Westbury on Severn

Westbury on Severn house

6 14 3 nights min

  • 6 bedrooms
  • sleeps 14
  • 3 nights min
  • Child Friendly
“Great” With family ages ranging from 18 months to 78 we were worried about how we would all fit in. But thanks to the layout, and several sitting areas, the whole week went without a hitch. The lovely house was in excellent condition, with the kitch
…see more

Price per night from

$222

Price per night from

$222

Distance approx 17.37 km from Chepstow

(6) Excellent 

7

Nympy barn cottage

Gloucestershire / Nympsfield

Nympsfield barn

2 4 min stay varies

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

Price per night from

$89

Price per night from

$89

Distance approx 15.19 km from Chepstow

(6) Very Good 

33

Aqueduct Cottage

Monmouthshire / Abergavenny

Abergavenny cottage

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Suitable for children age 5+
  • Pet Friendly

Price per night from

$183

Price per night from

$183

Distance approx 18.21 km from Chepstow

(23) Excellent 

17

Valley View Mews

Gloucestershire / Longhope

Longhope apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$76

Responds fast!
avg. 2 hours 40 minutes

Price per night from

$76

Distance approx 18.07 km from Chepstow

16

Mill Garden Lodge

Gloucestershire / Longhope

Longhope lodge

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Pet Friendly

Price per night from

$120

Price per night from

$120

Distance approx 14.55 km from Chepstow

(63) Very Good 

Certificate of Excellence

34

OneSpringBank

Stroud District / Dursley

Dursley cottage

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 20 mi
  • Child Friendly
  • Pet Friendly

Certificate of Excellence

Price per night from

$80

Responds fast!
avg. 1 hour 15 minutes

Price per night from

$80

Distance approx 14.85 km from Chepstow

(1) Excellent 

10

T68 Dethleff Sunlight 4 Berth Motorhome

Gloucestershire / Pucklechurch

Pucklechurch camper van

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$114

Price per night from

$114

Distance approx 14.01 km from Chepstow

(58) Very Good 

Certificate of Excellence

22

Wyewood Cottage

Ross-on-Wye / Symonds Yat

Symonds Yat cottage

2 4 min stay varies

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

Certificate of Excellence

Price per night from

$70

Responds fast!
avg. 51 minutes

Price per night from

$70

Distance approx 19.48 km from Chepstow

(24) Excellent 

Certificate of Excellence

23

Swallows Rest beautiful spacious barn conversion

Stroud / Nailsworth

Nailsworth barn

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Pet Friendly
  • Private garden

Certificate of Excellence

Price per night from

$101

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$101

Distance approx 11.99 km from Chepstow

(21) Excellent 

25

Christmas Cottage Two Bed Beautiful vintage style

Forest of Dean / Blakeney

Blakeney cottage

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$114

Responds fast!
avg. 47 minutes

Price per night from

$114

Distance approx 13.04 km from Chepstow

(16) Excellent 

24

Oak View Cottage

Monmouthshire / Monmouth

Monmouth house

3 6 min stay varies

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

Price per night from

$240

Price per night from

$240

Distance approx 16.95 km from Chepstow

(3) Average 

25

Court House, Owlpen, circa 1620

Cotswolds / Tetbury

Tetbury house

3 4 min stay varies

  • 3 bedrooms
  • sleeps 4
  • min stay varies
  • Suitable for children age 5+
  • Private garden

Price per night from

$189

Price per night from

$189

Distance approx 10.94 km from Chepstow

(26) Excellent 

19

The Old Chapel

Lydney / Yorkley

Yorkley converted chapel

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Nearest beach 90 mi
  • Suitable for children age 5+
  • Private garden

Price per night from

$114

Price per night from

$114

Distance approx 17.8 km from Chepstow

(14) Excellent 

Certificate of Excellence

21

Tree Tops Woodpecker Annexe

Herefordshire / Ross-on-Wye

Ross-on-Wye studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Ask about children
  • Private garden

Certificate of Excellence

Price per night from

$76

Responds fast!
avg. 2 hours 6 minutes

Price per night from

$76

Distance approx 15.61 km from Chepstow

(19) Excellent 

Certificate of Excellence

32

Birch Tree Barn

Abergavenny / Penpergwm

Penpergwm barn

2 4 min stay varies

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

Certificate of Excellence

Price per night from

$126

Responds fast!
avg. 3 hours 55 minutes

Price per night from

$126

Distance approx 19.36 km from Chepstow

(13) Excellent 

7

Owl Cottage

Somerset / Bath

Bath cottage

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies

Price per night from

$60

Responds fast!
avg. 3 hours 3 minutes

Price per night from

$60

Distance approx 16.02 km from Chepstow

15

The Grange Cottage

Cotswolds / Frampton on Severn

Frampton on Severn cottage

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 75 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$372

Responds fast!
avg. 3 hours 15 minutes

Price per night from

$372

Distance approx 10.36 km from Chepstow

(3) Excellent 

17

My Forest Cottage

Lydney / Parkend

Parkend cottage

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$126

Responds fast!
avg. 1 hour 15 minutes

Price per night from

$126

Distance approx 15.14 km from Chepstow

5

Brayne Court Bed & Breakfast - Jacobean Suite

Forest of Dean / Littledean

Littledean b and b

1 4 1 night min

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

Price per night from

$126

Price per night from

$126