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Book a cottage break in Chepstow, Monmouthshire, Wales

Showing all properties across the UK. Select a destination from the list to refine your search.
24 holiday rentals
Chepstow 10 miles away

High Cloud,

Monmouth, Monmouthshire, Wales
sleeps  24 sleeps 24
10 bedrooms 10 bedrooms
7 bathrooms 7 bathrooms
 3 dogs welcome  multi-dogs (up to 3)
family friendly family friendly

Experience something special at High Cloud with stunning panoramic views of the Welsh countryside, an outdoor swimming pool, a private hot tub, a games room and a location close to Sugarloaf Mountain plus accommodation for up to 24 people, ideal for large groups and big families.

5 (1 reviews)
countryside views over fields and farmlands near local pub
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomindoor hot tub accessoutdoor heated poolfree WifigardenBBQParking
7 nights from £4500
Next available: 08 Dec - 7 nights
Online Booking Available
Viewed 31 times recently.
Chepstow 14 miles away

Monnow Valley Studio,

Rockfield, Monmouthshire, Wales
sleeps  24 sleeps 24
11 bedrooms 11 bedrooms
10 bathrooms 10 bathrooms
no dogs allowed No pets
family friendly family friendly

Fascinating 11 bedroom holiday house, once a recording studio and visited by A-listers, now a big group holiday house with superb riverside location, party room, games room and warm bubbly outdoor hot tub, this is a house fit for stars.

ground floor bedroomensuite bedroom(s)
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomoutdoor hot tub accessfree Wifigardenwood burning stoveBBQParking
7 nights from £5850
Next available: 06 Dec - 7 nights
book online online booking
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Chepstow 15 miles away

The Anchor,

Lydbrook, Gloucestershire, England
sleeps  20 sleeps 20
7 bedrooms 7 bedrooms
7 bathrooms 7 bathrooms
 2 dogs welcome  2 dogs welcome
family friendly family friendly

Looking to rent a large holiday house in the Wye Valley? This 7/8 bedroom property in the Forest of Dean with its capacity to sleep up to 22 people, its pet-friendly policy, games room with table tennis, table football and pool table plus inviting warm bubbly private hot tub could be perfect for your group getaway.

ensuite bedroom(s) near local pub
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomoutdoor hot tub accessfree Wifienclosed gardenwood burning stoveBBQParking
7 nights from £4250
Next available: 07 Dec - 7 nights
Chepstow 15 miles away

Rockstowes House,

Dursley, Gloucestershire, England
sleeps  12 sleeps 12
6 bedrooms 6 bedrooms
5 bathrooms 5 bathrooms
 2 dogs welcome  2 dogs welcome
family friendly family friendly

Rockstowes House, a Grade II-listed holiday home in Gloucestershire's Cotswolds, sleeps 12, offers stunning countryside views, a hot tub, tennis courts, and is ideal for family gatherings; sorry, no pets allowed.

ground floor bedroomensuite bedroom(s)
Facilities, Features & Awards:
dishwasher in kitchenindoor hot tub accessfree WifigardenfireplaceParking
7 nights from £2258
Next available: 27 Mar - 6 nights
book online online booking
View
Romantic Retreat
Viewed 30 times recently.
no booking fee
Chepstow 19 miles away

Owl Cottage at Coombe Barn Cottages,

Bath, Somerset, England
sleeps  2 sleeps 2
1 bedrooms 1 bedroom
1 bathrooms 1 bathroom
no dogs allowed No pets

Idyllic couple’s no pets rural retreat, featuring stunning country views over the Somerset countryside, just 10 minutes’ drive from Bath.

ground floor bedroom near local pub
Facilities, Features & Awards:
TVmicrowave in kitchenfree WifiParking
7 nights from £445
Next available: 08 Dec - 3 nights
Online Booking Available
Viewed 31 times recently.
Chepstow 14 miles away

Wye Rapids House,

Symonds Yat, Herefordshire, England
sleeps  30 sleeps 30
13 bedrooms 13 bedrooms
12 bathrooms 12 bathrooms
 4 dogs welcome  multi-dogs (up to 4)
family friendly family friendly

Fabulous 13 bedroom pet-friendly riverside holiday home with games room and hot tub in Symonds Yet, sleeps 30.

ground floor bedroom river views
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomfree WifigardenBBQParking
7 nights from £5250
Next available: 07 Dec - 3 nights
book online online booking
View
Romantic Retreat
Viewed 28 times recently.
no booking fee
Chepstow 19 miles away

Badger at Coombe Barn Cottages,

Bath, Somerset, England
sleeps  2 sleeps 2
1 bedrooms 1 bedroom
1 bathrooms 1 bathroom
no dogs allowed No pets

Charming sleeps 2 romantic retreat in rural Somerset, set in idyllic countryside on a working farm, just 10 minutes’ drive from Bath.

ensuite bedroom(s) near local pub
Facilities, Features & Awards:
TVmicrowave in kitchenfree WifiPatio GardenParking
7 nights from £445
Next available: 07 Dec - 4 nights
Chepstow 17 miles away

Pencraig Court,

Pencraig, Herefordshire, England
sleeps  36 sleeps 36
11 bedrooms 11 bedrooms
11 bathrooms 11 bathrooms
 5 dogs welcome  multi-dogs (up to 5)
family friendly family friendly

Elegant 11 bedroom country house set in beautiful gardens in the Wye Valley AONB, complete with games room with pool, table tennis and table football, just 6 miles from Ross on Wye.

ensuite bedroom(s) river views
Facilities, Features & Awards:
smart TVdishwasher in kitchenmicrowave in kitchengames roomfree Wifigardenwood burning stoveBBQParking
7 nights from £5750
Next available: 07 Dec - 5 nights
book online online booking
View
Chepstow 18 miles away

Ingleside Family Cottage, Cotswolds,

Adsett, Gloucestershire, England
sleeps  14 sleeps 14
6 bedrooms 6 bedrooms
4 bathrooms 4 bathrooms
no dogs allowed No pets
family friendly family friendly

Large family-friendly 6 bedroom holiday cottage and beautiful mature garden, nestled in a rural hamlet near to the Forest of Dean and within easy reach of the Cotswold Hills and Area of Outstanding Natural Beauty.

ensuite bedroom(s)
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomfree Wifigardenwood burning stovefireplaceParking
7 nights from £1855
Next available: 08 Jan - 4 nights
book online online booking
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Chepstow 14 miles away

Holly Tree House,

Symonds Yat, Herefordshire, England
sleeps  22 sleeps 22
9 bedrooms 9 bedrooms
8 bathrooms 8 bathrooms
 3 dogs welcome  multi-dogs (up to 3)
family friendly family friendly

With wonderful views over the River Wye, a superb location in the Wye Valley, spacious stylish accommodation and a warm bubbly outdoor private hot tub, this 9 bedroom country house has to be one of the best places for large groups of friends or family to holiday altogether close to Ross on Wye.

ensuite bedroom(s) river views
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomoutdoor hot tub accessfree WifigardenfireplaceBBQParking
7 nights from £4500
Next available: 06 Dec - 6 nights
no booking fee
Chepstow 19 miles away

Trevase Granary,

Hereford, Herefordshire, England
sleeps  18 sleeps 18
8 bedrooms 8 bedrooms
8 bathrooms 8 bathrooms
no dogs allowed No pets
family friendly family friendly

Choose from two award winning 5 star rated luxury barn conversions, each sleeping up to 18 guests, close to the Wye Valley and with stunning countryside views, a private garden, games room and hot tub for relaxing holidays.

5 (5 reviews)
ensuite bedroom(s) countryside views over fields and farmlands
Facilities, Features & Awards:
gold award winning cottageTVdishwasher in kitchenmicrowave in kitchengames roomoutdoor private hot tubfree Wifienclosed gardenBBQParking
7 nights from £3360
Next available: 08 Dec - 4 nights
book online online booking
View
Chepstow 14 miles away

Symonds Yat Lodge,

Symonds Yat, Herefordshire, England
sleeps  57 sleeps 57
25 bedrooms 25 bedrooms
25 bathrooms 25 bathrooms
 7 dogs welcome  multi-dogs (up to 7)
family friendly family friendly

Large group holiday home in the Wye Valley with 25 ensuite bedrooms, a games room, party room and bar, ideal for special celebrations like hen parties and even weddings! Licensed wedding venue.

ensuite bedroom(s) river views
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomfree Wifigardenwood burning stovefireplaceBBQParking
7 nights from £7500
Next available: 07 Dec - 3 nights
Family-Friendly
Viewed 49 times recently.
Chepstow 11 miles away

Forest House,

Coleford, Gloucestershire, England
sleeps  26 sleeps 26
11 bedrooms 11 bedrooms
11 bathrooms 11 bathrooms
 3 dogs welcome  multi-dogs (up to 3)
family friendly family friendly

Large group holiday house on edge of Forest of Dean and close to the Wye Valley, complete with 11 bedrooms, hot tub, bar and large sociable living spaces.

ground floor bedroomensuite bedroom(s)
Facilities, Features & Awards:
smart TVdishwasher in kitchenmicrowave in kitchengames roomfree Wifigardenwood burning stoveBBQParking
7 nights from £4950
Next available: 06 Dec - 5 nights
Romantic Retreat
Viewed 30 times recently.
no booking fee
Chepstow 19 miles away

Hare Romantic Retreat,

Bath, Somerset, England
sleeps  2 sleeps 2
1 bedrooms 1 bedroom
1 bathrooms 1 bathroom
no dogs allowed No pets

No pets sleeps 2 Cotswolds rural retreat just 4 miles from Bath, with veranda with fabulous countryside views.

ground floor bedroom countryside views over fields and farmlands
Facilities, Features & Awards:
TVmicrowave in kitchenfree WifiParking
7 nights from £445
Next available: 08 Dec - 3 nights
Chepstow 13 miles away

The Manor on the Monnow,

Monmouth, Monmouthshire, Wales
sleeps  24 sleeps 24
11 bedrooms 11 bedrooms
9 bathrooms 9 bathrooms
 3 dogs welcome  multi-dogs (up to 3)
family friendly family friendly

Spacious 11 bedroom country house rental on outskirts of Monmouth with warm bubbly indoor hot tub, games room with table tennis, pool plus table football and 2 acres of gardens complete with children’s play facilities.

ensuite bedroom(s) rural views
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomindoor hot tub accessfree Wifigardenwood burning stoveBBQParking
7 nights from £4950
Next available: 07 Dec - 5 nights
* Price quoted is not inclusive of any applicable booking fees or local charges.

Do feel free to share your experience of a holiday in Chepstow with visitors to Country Cottages Online.

Any country cottages, chalets in Chepstow will be shown underneath. Click on the property photographs to read all about each holiday home, a description of the rental accommodation in terms of layout, the surrounding countryside and tourist attractions.

It may prove useful doing some research before your proposed holiday to Chepstow. Find out what is happening on the dates you plan to be there - there may be a regional show that you might wish to experience. Most people on holiday like to shop at the local markets, and perhaps enjoy meals out. Having tourist information about Chepstow at your fingertips means that you can get the most from your trip. Ask your hosts about the best walks and anything else you might need to know ?they have first-hand experience of living near Chepstow.

Sometimes it is good to take a chance and visit somewhere off the beaten track, that is not at all tourist driven. Have a wonderful time visiting Chepstow, best wishes for good weather and a safe holiday.

Whether you choose to book a holiday cottage in Chepstow, an apartment, a lodge or another type of self-catering holiday accommodation, we hope you have your best holiday yet in Monmouthshire.

Frequently Asked Questions about Chepstow

The best places to stay depend on your preferences, interests and the type of accommodation that best suits you. Country Cottages Online features a great selection of good quality rentals.
See our selection of pet-friendly rentals in Chepstow, or use the filters to refine your search.
See our selection of lodges and cabins in Chepstow, Monmouthshire.
Read the description of Chepstow to find out ideas and tips on the best things to see and do. Also see our area guides for more information on what Monmouthshire has to offer for holidaymakers.

Chepstow Holiday Rental Searches