10 Best Vacation Rentals in Chepstow - Holiday Lettings - Cabins

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12 Vacation rentals

(24) Excellent 

5

Itton Vacation barn rental

Chepstow / Itton

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
Dolly's Barn is a light airy recently converted single storey small barn with lovely views to the surrounding countryside. An open plan roomy lounge/kitchen which has stripped wooden floors and kemin rugs, contemporary furnishings and wood-burning stove. It's also ce …see more

from $104 / night

$439 - $542 / week

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from $104 / night

(59) Excellent 

8

Itton Vacation cottage rental

Chepstow / Itton

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Clare's Cottage is pet friendly with a home from home atmosphere. It has the country 'must have' of a wood-burning stove together with eco friendly central heating. There is a separate fully fitted kitchen with small breakfast table with views to the garden and bird f …see more

from $110 / night

$465 - $678 / week

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from $110 / night

35

Vacation home in Chepstow

Monmouthshire / Chepstow

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
If you have ever fancied staying in an old Manor House then you will love this place. Roaring log fires in the winter and a walled garden in the summer, it is a real find. Split into two separate homes this historic house would suit business travellers and /or families …see more

from $387 / night

$2709 / week

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from $387 / night

(13) Excellent 

Certificate of Excellence

24

Vacation cottage in Brockweir

Chepstow / Brockweir

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 90 mi
  • Private garden
This four star detached stone cottage provides a rural retreat as a base for relaxing and enjoying outdoor activities. Tastefully and thoughtfully converted it is perfectly suited to two people. The accommodation comprises one bedroom, an open plan lounge-diner, and …see more

Certificate of Excellence

from $97 / night

$452 - $568 / week

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Responds fast!
avg. 2 hours 44 minutes

from $97 / night

(11) Excellent 

19

Vacation cottage in Gaerllwyd

Chepstow / Gaerllwyd

3 4 2 nights min

  • 3 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
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 (shared with one other cottage), large play area and games room. It is the perfect location to explore the attractions and …see more

from $181 / night

$772 - $1114 / week

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Responds fast!
avg. 3 hours 34 minutes

from $181 / night

(14) Very Good 

19

Vacation cottage in Brockweir

Chepstow / Brockweir

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 100 mi
  • Child friendly
  • Pet friendly
Spring Cottage enjoys a beautiful setting surrounded by indigenous forest set above the River Wye, only 5 minutes from Tintern. Visit Wales accredited with 5 stars, the cottage features two spacious bedrooms, kitchen with dining area, lounge with wood burner, detached c …see more

from $92 / night

$600 - $924 / week

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Responds fast!
avg. 2 hours 17 minutes

from $92 / night

(9) Very Good 

21

Vacation cottage rental

Chepstow / Gaerllwyd

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Maes y Felin is a Holiday Cottage with a shared 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. It is the perfect location to explore the attractions and sights …see more

from $181 / night

$772 - $1114 / week

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Responds fast!
avg. 3 hours 34 minutes

from $181 / night

(57) Excellent 

17

Vacation tower with golf nearby in Mathern

Chepstow / Mathern

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
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 fairy tale castle. Stay …see more

from $213 / night

$633 / week

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from $213 / night

(2) Very Good 

19

Chepstow Vacation home rental

Monmouthshire / Chepstow

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Car not necessary
BroadRock holiday let is located in a unique position, the Offa's Dyke footpath runs through the garden with the house nestled on top of the Wye Valley cliffs. Located 1 mile outside of Chepstow town this is the perfect house to explore this area of outstanding natural …see more

from $323 / night

$1935 - $2838 / week

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from $323 / night

26

Chepstow Vacation b&b rental

Monmouthshire / Chepstow

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden
Ty’r Castell - (Welsh for ‘House of the Castle’) is a Grade II listed town house in Bridge Street, which leads from Chepstow (Welsh: Cas-gwent) town centre to the famous bridge crossing the River Wye between Wales and England. This three storey recently renovated town …see more

from $194 / night

$1290 / week

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from $194 / night

(58) Excellent 

19

Chepstow Vacation cottage rental

Monmouthshire / Chepstow

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Pet friendly
Detached 2 bed-roomed cottage sleeps up to 4 set in its own delightful lovingly tended garden with fabulous views to the surrounding Welsh countryside. Perfectly placed for exploring Wye Valley, Vale of Usk, Royal Forest of Dean and yet only 3 miles from the popular bo …see more

from $117 / night

$516 / week

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Responds fast!
avg. 1 hour 53 minutes

from $117 / night

(23) Excellent 

12

Home rental in Chepstow

Monmouthshire / Chepstow

1 2 6 nights min

  • 1 bedroom
  • Sleeps 2
  • 6 nights min
  • Child friendly
  • Pet friendly
A lovely light and airy property which has recently been converted from a stone outbuilding. Situated in a paddock presently being restored to a wild flower meadow. It has stunning views from each window. The open plan fully fitted kitchen/iiving room has stripped woode …see more

from $117 / night

$504 / week

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Responds fast!
avg. 1 hour 53 minutes

from $117 / night