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Chepstow Vacation Rentals

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50 rentals in Chepstow.
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The Welsh Gatehouse - Like living in your very own castle, vacation rental in Chepstow
The Welsh Gatehouse - Like living in your very own castle, vacation rental in Chepstow
The Welsh Gatehouse - Like living in your very own castle, vacation rental in Chepstow

The Welsh Gatehouse - Like living in your very own castle

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Pet friendly Clares  Holiday Cottage with stunning views & green credentials, vacation rental in Chepstow
Pet friendly Clares  Holiday Cottage with stunning views & green credentials, vacation rental in Chepstow
Pet friendly Clares  Holiday Cottage with stunning views & green credentials, vacation rental in Chepstow

Pet friendly Clares Holiday Cottage with stunning views & green credentials

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Oakgrove Cottage , vacation rental in Chepstow
Oakgrove Cottage , vacation rental in Chepstow
Oakgrove Cottage , vacation rental in Chepstow

Oakgrove Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Dog friendly Dolly's Barn Barn with stunning views & green credentials, vacation rental in Chepstow
Dog friendly Dolly's Barn Barn with stunning views & green credentials, vacation rental in Chepstow
Dog friendly Dolly's Barn Barn with stunning views & green credentials, vacation rental in Chepstow

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Ty'r Castell Band B, Chepstow, Monmouthshire, vacation rental in Chepstow
Ty'r Castell Band B, Chepstow, Monmouthshire, vacation rental in Chepstow
Ty'r Castell Band B, Chepstow, Monmouthshire, vacation rental in Chepstow

Ty'r Castell Band B, Chepstow, Monmouthshire

Private Room
2 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
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The Loft at BroadRock, vacation rental in Chepstow
The Loft at BroadRock, vacation rental in Chepstow
The Loft at BroadRock, vacation rental in Chepstow

The Loft at BroadRock

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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If you have ever fancied staying in an old Manor House  you will love it here, vacation rental in Chepstow
If you have ever fancied staying in an old Manor House  you will love it here, vacation rental in Chepstow
If you have ever fancied staying in an old Manor House  you will love it here, vacation rental in Chepstow

If you have ever fancied staying in an old Manor House you will love it here

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Clock Cottage - Luxury 2 bed Holiday Let, vacation rental in Chepstow
Clock Cottage - Luxury 2 bed Holiday Let, vacation rental in Chepstow
Clock Cottage - Luxury 2 bed Holiday Let, vacation rental in Chepstow

Clock Cottage - Luxury 2 bed Holiday Let

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Trewyn, Chepstow, vacation rental in Chepstow
Trewyn, Chepstow, vacation rental in Chepstow
Trewyn, Chepstow, vacation rental in Chepstow

Trewyn, Chepstow

Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Caradoc, Chepstow, vacation rental in Chepstow
Caradoc, Chepstow, vacation rental in Chepstow
Caradoc, Chepstow, vacation rental in Chepstow

Caradoc, Chepstow

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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The Outlook, vacation rental in Chepstow
The Outlook, vacation rental in Chepstow
The Outlook, vacation rental in Chepstow

The Outlook

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Welsh Gatehouse: Luxury 13th Century Medieval Historic Home, vacation rental in Chepstow
Welsh Gatehouse: Luxury 13th Century Medieval Historic Home, vacation rental in Chepstow
Welsh Gatehouse: Luxury 13th Century Medieval Historic Home, vacation rental in Chepstow

Welsh Gatehouse: Luxury 13th Century Medieval Historic Home

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Grand Georgian 3 Storey Home with Private Gardens and Parking, vacation rental in Chepstow
Grand Georgian 3 Storey Home with Private Gardens and Parking, vacation rental in Chepstow
Grand Georgian 3 Storey Home with Private Gardens and Parking, vacation rental in Chepstow

Grand Georgian 3 Storey Home with Private Gardens and Parking

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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The Honey Pot, CHEPSTOW, vacation rental in Chepstow
The Honey Pot, CHEPSTOW, vacation rental in Chepstow
The Honey Pot, CHEPSTOW, vacation rental in Chepstow

The Honey Pot, CHEPSTOW

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tintern Abbey Cottage, vacation rental in Chepstow
Tintern Abbey Cottage, vacation rental in Chepstow
Tintern Abbey Cottage, vacation rental in Chepstow

Tintern Abbey Cottage

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Traditional Country Cottage With Truly Amazing Views Over The River Wye

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Detached barn, with breathtaking views across the Wye Valley, vacation rental in Chepstow
Detached barn, with breathtaking views across the Wye Valley, vacation rental in Chepstow
Detached barn, with breathtaking views across the Wye Valley, vacation rental in Chepstow

Detached barn, with breathtaking views across the Wye Valley

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The Outlook at Underwood Farm with fantastic view and own private Hot Tub, vacation rental in Chepstow
The Outlook at Underwood Farm with fantastic view and own private Hot Tub, vacation rental in Chepstow
The Outlook at Underwood Farm with fantastic view and own private Hot Tub, vacation rental in Chepstow

The Outlook at Underwood Farm with fantastic view and own private Hot Tub

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Foxes Reach (Holiday Cottage  Nr Tintern, Wales) , vacation rental in Chepstow
Foxes Reach (Holiday Cottage  Nr Tintern, Wales) , vacation rental in Chepstow
Foxes Reach (Holiday Cottage  Nr Tintern, Wales) , vacation rental in Chepstow

Foxes Reach (Holiday Cottage Nr Tintern, Wales)

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Two bedroom Private cottage with an acre of garden in the Forest of Dean , vacation rental in Chepstow
Two bedroom Private cottage with an acre of garden in the Forest of Dean , vacation rental in Chepstow
Two bedroom Private cottage with an acre of garden in the Forest of Dean , vacation rental in Chepstow

Two bedroom Private cottage with an acre of garden in the Forest of Dean

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Studio Barn, vacation rental in Chepstow
The Studio Barn, vacation rental in Chepstow
The Studio Barn, vacation rental in Chepstow

The Studio Barn

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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800 Year Old Manor House, Holiday Home, Stay in Luxury., vacation rental in Chepstow
800 Year Old Manor House, Holiday Home, Stay in Luxury., vacation rental in Chepstow
800 Year Old Manor House, Holiday Home, Stay in Luxury., vacation rental in Chepstow

800 Year Old Manor House, Holiday Home, Stay in Luxury.

Rental Home
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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The Hudnalls Hideout - Luxury Wye Valley Treehouse, vacation rental in Chepstow
The Hudnalls Hideout - Luxury Wye Valley Treehouse, vacation rental in Chepstow
The Hudnalls Hideout - Luxury Wye Valley Treehouse, vacation rental in Chepstow

The Hudnalls Hideout - Luxury Wye Valley Treehouse

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Peaceful Cottage situated in the picturesque Forest of Dean, vacation rental in Chepstow
Peaceful Cottage situated in the picturesque Forest of Dean, vacation rental in Chepstow
Peaceful Cottage situated in the picturesque Forest of Dean, vacation rental in Chepstow

Peaceful Cottage situated in the picturesque Forest of Dean

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Retreat luxury Holiday Accommodation with Fantastic views and a Hot Tub, vacation rental in Chepstow
The Retreat luxury Holiday Accommodation with Fantastic views and a Hot Tub, vacation rental in Chepstow
The Retreat luxury Holiday Accommodation with Fantastic views and a Hot Tub, vacation rental in Chepstow

The Retreat luxury Holiday Accommodation with Fantastic views and a Hot Tub

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Welsh Marches - Skirrid, vacation rental in Chepstow
Welsh Marches - Skirrid, vacation rental in Chepstow
Welsh Marches - Skirrid, vacation rental in Chepstow

Welsh Marches - Skirrid

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Anne's Hut (Monmouthshire), vacation rental in Chepstow
Anne's Hut (Monmouthshire), vacation rental in Chepstow
Anne's Hut (Monmouthshire), vacation rental in Chepstow

Anne's Hut (Monmouthshire)

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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The Comfy Cow, Raglan, vacation rental in Chepstow
The Comfy Cow, Raglan, vacation rental in Chepstow
The Comfy Cow, Raglan, vacation rental in Chepstow

The Comfy Cow, Raglan

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Resilient Woodlands Retreat - Coppice Cabin, vacation rental in Chepstow
Resilient Woodlands Retreat - Coppice Cabin, vacation rental in Chepstow
Resilient Woodlands Retreat - Coppice Cabin, vacation rental in Chepstow

Resilient Woodlands Retreat - Coppice Cabin

Cabin
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Orchard Cottage (Monmouthshire), vacation rental in Chepstow
Orchard Cottage (Monmouthshire), vacation rental in Chepstow
Orchard Cottage (Monmouthshire), vacation rental in Chepstow

Orchard Cottage (Monmouthshire)

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Resilient Woodlands Retreat - Woodsman's Cabin, vacation rental in Chepstow
Resilient Woodlands Retreat - Woodsman's Cabin, vacation rental in Chepstow
Resilient Woodlands Retreat - Woodsman's Cabin, vacation rental in Chepstow

Resilient Woodlands Retreat - Woodsman's Cabin

Cabin
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Welsh Marches - Sugar Loaf, vacation rental in Chepstow
Welsh Marches - Sugar Loaf, vacation rental in Chepstow
Welsh Marches - Sugar Loaf, vacation rental in Chepstow

Welsh Marches - Sugar Loaf

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Welsh Marches - Blorenge, vacation rental in Chepstow
Welsh Marches - Blorenge, vacation rental in Chepstow
Welsh Marches - Blorenge, vacation rental in Chepstow

Welsh Marches - Blorenge

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Old Garden View - Delightful  Apartment in the Forest of Dean, vacation rental in Chepstow
Old Garden View - Delightful  Apartment in the Forest of Dean, vacation rental in Chepstow
Old Garden View - Delightful  Apartment in the Forest of Dean, vacation rental in Chepstow

Old Garden View - Delightful Apartment in the Forest of Dean

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Netherend Inn, Woolaston, vacation rental in Chepstow
Netherend Inn, Woolaston, vacation rental in Chepstow
Netherend Inn, Woolaston, vacation rental in Chepstow

Netherend Inn, Woolaston

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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THE PIGGERY, 3 bedrooms and perfect for those with limited mobility, Lydney, vacation rental in Chepstow
THE PIGGERY, 3 bedrooms and perfect for those with limited mobility, Lydney, vacation rental in Chepstow
THE PIGGERY, 3 bedrooms and perfect for those with limited mobility, Lydney, vacation rental in Chepstow

THE PIGGERY, 3 bedrooms and perfect for those with limited mobility, Lydney

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Golden Valley Barn, Oldbury-On-Severn, vacation rental in Chepstow
Golden Valley Barn, Oldbury-On-Severn, vacation rental in Chepstow
Golden Valley Barn, Oldbury-On-Severn, vacation rental in Chepstow

Golden Valley Barn, Oldbury-On-Severn

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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The Piggery, WOOLASTON, vacation rental in Chepstow
The Piggery, WOOLASTON, vacation rental in Chepstow
The Piggery, WOOLASTON, vacation rental in Chepstow

The Piggery, WOOLASTON

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Birch Cottage - Eco Retreat, vacation rental in Chepstow
Birch Cottage - Eco Retreat, vacation rental in Chepstow
Birch Cottage - Eco Retreat, vacation rental in Chepstow

Birch Cottage - Eco Retreat

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Alvia, Portskewett, vacation rental in Chepstow
Alvia, Portskewett, vacation rental in Chepstow
Alvia, Portskewett, vacation rental in Chepstow

Alvia, Portskewett

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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The Honey Pot, Chepstow, vacation rental in Chepstow
The Honey Pot, Chepstow, vacation rental in Chepstow
The Honey Pot, Chepstow, vacation rental in Chepstow

The Honey Pot, Chepstow

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Luxury Cottage with hot tub in the Forest of Dean, vacation rental in Chepstow
Luxury Cottage with hot tub in the Forest of Dean, vacation rental in Chepstow
Luxury Cottage with hot tub in the Forest of Dean, vacation rental in Chepstow

Luxury Cottage with hot tub in the Forest of Dean

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Modern 1-Bed Apartment in Caldicot, self check in, vacation rental in Chepstow
Modern 1-Bed Apartment in Caldicot, self check in, vacation rental in Chepstow
Modern 1-Bed Apartment in Caldicot, self check in, vacation rental in Chepstow

Modern 1-Bed Apartment in Caldicot, self check in

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Luxury Cottage with hot tub in the Forest of Dean, vacation rental in Chepstow
Luxury Cottage with hot tub in the Forest of Dean, vacation rental in Chepstow
Luxury Cottage with hot tub in the Forest of Dean, vacation rental in Chepstow

Luxury Cottage with hot tub in the Forest of Dean

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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'La Villa Olli'-Natural Pool & Hot Tub, vacation rental in Chepstow
'La Villa Olli'-Natural Pool & Hot Tub, vacation rental in Chepstow
'La Villa Olli'-Natural Pool & Hot Tub, vacation rental in Chepstow

'La Villa Olli'-Natural Pool & Hot Tub

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Ferienhaus Catbrook für 1 - 6 Personen mit 4 Schlafzimmern - Ferienhaus, vacation rental in Chepstow
Ferienhaus Catbrook für 1 - 6 Personen mit 4 Schlafzimmern - Ferienhaus, vacation rental in Chepstow
Ferienhaus Catbrook für 1 - 6 Personen mit 4 Schlafzimmern - Ferienhaus, vacation rental in Chepstow

Ferienhaus Catbrook für 1 - 6 Personen mit 4 Schlafzimmern - Ferienhaus

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Netherend Inn, WOOLASTON, vacation rental in Chepstow
Netherend Inn, WOOLASTON, vacation rental in Chepstow
Netherend Inn, WOOLASTON, vacation rental in Chepstow

Netherend Inn, WOOLASTON

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Modern 1-Bed Apartment in Caldicot, self check in, vacation rental in Chepstow
Modern 1-Bed Apartment in Caldicot, self check in, vacation rental in Chepstow
Modern 1-Bed Apartment in Caldicot, self check in, vacation rental in Chepstow

Modern 1-Bed Apartment in Caldicot, self check in

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Peaceful country cottage with beautiful river views, family and dog friendly, vacation rental in Chepstow
Peaceful country cottage with beautiful river views, family and dog friendly, vacation rental in Chepstow
Peaceful country cottage with beautiful river views, family and dog friendly, vacation rental in Chepstow

Peaceful country cottage with beautiful river views, family and dog friendly

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Medieval Priory Grange, vacation rental in Chepstow
Medieval Priory Grange, vacation rental in Chepstow
Medieval Priory Grange, vacation rental in Chepstow

Medieval Priory Grange

Rental Home
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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