
Photo by Pam Brophy (CC BY-SA)
Holiday rentals near Chepstow Castle
We found 1,318 holiday rentals — enter your dates for availability
If you want to to stay within easy reach of Chepstow Castle, take a look at private holiday rentals to find the perfect home base for your trip. Whether you're staying in a holiday rental with friends, family or just with your pet, you'll find the amenities that you need and want, including air conditioning and Wi-Fi. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Chepstow Castle
Showing deals for:7 Nov - 14 Nov
Image gallery for Indoor heated swimming Pool, Hot tub sleeps up to 30..Amazing Riverside House

9.69.6 out of 10 rating
Exceptional
(19 reviews)
Indoor heated swimming Pool, Hot tub sleeps up to 30..Amazing Riverside House
Gloucester, ENG
14% off
Price is AU$23,936
AU$23,936
AU$3,419 per night
includes taxes & fees
Image gallery for HEATED OUTDOOR POOL(SEASONAL) /LUXURY HOT TUB -SLEEPS 18 + 8 FAMILIES ONLY

1010 out of 10 rating
Exceptional
(74 reviews)
HEATED OUTDOOR POOL(SEASONAL) /LUXURY HOT TUB -SLEEPS 18 + 8 FAMILIES ONLY
Dursley, DURSLEY
28% off
Price is AU$22,869
AU$22,869
AU$3,267 per night
includes taxes & fees
Image gallery for Wisteria View with Log Cabin sleeps 20 with hot tub

1010 out of 10 rating
Exceptional
(10 reviews)
Wisteria View with Log Cabin sleeps 20 with hot tub
Chippenham, England
14% off
Price is AU$15,553
AU$15,553
AU$2,222 per night
includes taxes & fees
Image gallery for Forest of Dean Romantic & Rustic Holiday Cottage

9.89.8 out of 10 rating
Exceptional
(41 reviews)
Forest of Dean Romantic & Rustic Holiday Cottage
Lydney, ENG
7% off
Price is AU$1,673
AU$1,673
AU$239 per night
includes taxes & fees
Image gallery for Central Bristol/Bath both 9 mins by train - by river, park in Conservation Area

1010 out of 10 rating
Exceptional
(5 reviews)
Central Bristol/Bath both 9 mins by train - by river, park in Conservation Area
Bristol, England
9% off
Price is AU$3,533
AU$3,533
AU$505 per night
includes taxes & fees
Image gallery for Charming, historic mill close to the Cotswold Way in North Nibley<br>

9.89.8 out of 10 rating
Exceptional
(91 reviews)
Charming, historic mill close to the Cotswold Way in North Nibley<br>
Dursley, England
13% off
Price is AU$5,798
AU$5,798
AU$828 per night
includes taxes & fees
Image gallery for Newly converted pigsty with amazing views. One small dog welcome.

1010 out of 10 rating
Exceptional
(42 reviews)
Newly converted pigsty with amazing views. One small dog welcome.
Dursley, England
9% off
Price is AU$2,484
AU$2,484
AU$355 per night
includes taxes & fees
Image gallery for Stunning 5 bedroom family home with unrivalled views

1010 out of 10 rating
Exceptional
(9 reviews)
Stunning 5 bedroom family home with unrivalled views
Pontypool, Wales
23% off
Price is AU$5,974
AU$5,974
AU$853 per night
includes taxes & fees
Image gallery for Luxury Mountain Holiday Property & Wellness Retreat with Sauna, Pool & Hot Tub.

9.89.8 out of 10 rating
Exceptional
(46 reviews)
Luxury Mountain Holiday Property & Wellness Retreat with Sauna, Pool & Hot Tub.
Abergavenny
9% off
Price is AU$12,386
AU$12,386
AU$1,769 per night
includes taxes & fees
Image gallery for Peaceful Quality 2 bedroom/2 bathrooms Country House Apartment:beautiful garden

1010 out of 10 rating
Exceptional
(48 reviews)
Peaceful Quality 2 bedroom/2 bathrooms Country House Apartment:beautiful garden
Ross-on-Wye, ENG
46% off
Price is AU$1,202
AU$1,202
AU$172 per night
includes taxes & fees
Image gallery for Luxury Self Catering Cottage in Historic Village Setting in the Forest of Dean

1010 out of 10 rating
Exceptional
(54 reviews)
Luxury Self Catering Cottage in Historic Village Setting in the Forest of Dean
Coleford
23% off
Price is AU$2,594
AU$2,594
AU$371 per night
includes taxes & fees
Image gallery for Cosy Cottage on the Cotswold Way

1010 out of 10 rating
Exceptional
(10 reviews)
Cosy Cottage on the Cotswold Way
Wotton-under-Edge, England
14% off
Price is AU$1,723
AU$1,723
AU$246 per night
includes taxes & fees
Image gallery for Country Cottage With Truly Amazing Views Over The River Wye valley. Pet friendly

9.89.8 out of 10 rating
Exceptional
(224 reviews)
Country Cottage With Truly Amazing Views Over The River Wye valley. Pet friendly
Monmouth, Wales
9% off
Price is AU$1,780
AU$1,780
AU$254 per night
includes taxes & fees
Image gallery for The Hall - luxury barn conversion in the Cotwolds

1010 out of 10 rating
Exceptional
(18 reviews)
The Hall - luxury barn conversion in the Cotwolds
Chipping Sodbury, England
13% off
Price is AU$1,740
AU$1,740
AU$249 per night
includes taxes & fees
Image gallery for The Annexe Yew Tree Cottage: A Tranquil Retreat for 2 near Bath & Bristol –

1010 out of 10 rating
Exceptional
(33 reviews)
The Annexe Yew Tree Cottage: A Tranquil Retreat for 2 near Bath & Bristol –
Bristol, ENG
9% off
Price is AU$1,439
AU$1,439
AU$206 per night
includes taxes & fees
Image gallery for Barn conversion in beautiful countryside, sleeps 4

9.69.6 out of 10 rating
Exceptional
(96 reviews)
Barn conversion in beautiful countryside, sleeps 4
Abergavenny, Wales
23% off
Price is AU$1,133
AU$1,133
AU$162 per night
includes taxes & fees
Image gallery for A terraced mews cottage close to the banks of the River Wye with beautiful views

9.69.6 out of 10 rating
Exceptional
(69 reviews)
A terraced mews cottage close to the banks of the River Wye with beautiful views
Ross-on-Wye, ENG
18% off
Price is AU$1,388
AU$1,388
AU$198 per night
includes taxes & fees
Image gallery for Beautiful "ECO" barn conversion in Wye Valley - ideal for couples plus two kids

9.69.6 out of 10 rating
Exceptional
(23 reviews)
Beautiful "ECO" barn conversion in Wye Valley - ideal for couples plus two kids
Monmouth, WLS
12% off
Price is AU$1,623
AU$1,623
AU$232 per night
includes taxes & fees
Image gallery for Acorn Cottage, Little Howle Farm. Luxury, peace, calm. Near Ross on Wye

1010 out of 10 rating
Exceptional
(49 reviews)
Acorn Cottage, Little Howle Farm. Luxury, peace, calm. Near Ross on Wye
Ross-on-Wye, England
17% off
Price is AU$1,611
AU$1,611
AU$230 per night
includes taxes & fees
Image gallery for Barns on The Kymin, Monmouth. Rural location with lovely views. Sleeps 10/12

1010 out of 10 rating
Exceptional
(11 reviews)
Barns on The Kymin, Monmouth. Rural location with lovely views. Sleeps 10/12
Monmouth, Wales
9% off
Price is AU$4,831
AU$4,831
AU$690 per night
includes taxes & fees
Image gallery for Cotswolds Barn Apartment - luxury self catering near Bath & Bristo

9.89.8 out of 10 rating
Exceptional
(6 reviews)
Cotswolds Barn Apartment - luxury self catering near Bath & Bristo
Chipping Sodbury, England
9% off
Price is AU$1,921
AU$1,921
AU$274 per night
includes taxes & fees
Image gallery for The Barn, Park Farm near Chew Magna, Bristol

1010 out of 10 rating
Exceptional
(9 reviews)
The Barn, Park Farm near Chew Magna, Bristol
Bristol, England
30% off
Price is AU$1,346
AU$1,346
AU$192 per night
includes taxes & fees
Image gallery for The Funky Pigsty-An adventure pet friendly paradise, Situated in the Wye Valley!

9.89.8 out of 10 rating
Exceptional
(10 reviews)
The Funky Pigsty-An adventure pet friendly paradise, Situated in the Wye Valley!
Coleford, Glos
27% off
Price is AU$1,144
AU$1,144
AU$163 per night
includes taxes & fees
Image gallery for Spacious Eco, Pet Friendly Apartments, Forest of Dean, Wye Valley

9.69.6 out of 10 rating
Exceptional
(54 reviews)
Spacious Eco, Pet Friendly Apartments, Forest of Dean, Wye Valley
Lydney, ENG
9% off
Price is AU$1,164
AU$1,164
AU$166 per night
includes taxes & fees
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Find properties near top attractions in Chepstow Castle
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Find the best place to stay - Chepstow Castle
Luxury 6 Bed House, Hot Tub, Games Room and in Walking Distance to Village Pub
Sleeps 17 · 6 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
139 reviews(139 reviews)
HEATED OUTDOOR POOL(SEASONAL) /LUXURY HOT TUB -SLEEPS 18 + 8 FAMILIES ONLY
Sleeps 26 · 9 bedrooms · 7 bathrooms
1010 out of 10
Exceptionalexceptional
74 reviews(74 reviews)
Spacious Eco, Pet Friendly Apartments, Forest of Dean, Wye Valley
Sleeps 4 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
54 reviews(54 reviews)
Peaceful, Cosy Cottage in the Forest of Dean Overlooking Common Land.
Sleeps 5 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
168 reviews(168 reviews)
A one bedroom self catering property in an idyllic valley setting.
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
70 reviews(70 reviews)
Amazing location large spacious 3 storey Georgian listed building sleeps 15
Sleeps 15 · 5 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
28 reviews(28 reviews)
Top rated rentals - Chepstow Castle
Stay in Ross on Wye
1010 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
Clean and tidy, beds very comfortable and it had everything we needed
terry k.
Stayed Apr 2025
Apartment in converted church
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Well appointed apartment ideal for a couple. Nicely situated between Bath and Bristol. Couple of pubs with easy walking distance. Was very clean and tidy. The spiral staircase up to the living area is novel. We’d stay there again.
Mark H.
Stayed Oct 2024
Gorgeous cottage close to Bristol
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
We loved staying here! Barnaby was always responsive and helpful. We were particularly fond of Jakey, the resident peacock. We’ll stay longer next time !
Bruce S.
Stayed May 2024
Well above expectations
1010 out of 10
Exceptionalexceptional
129 reviews(129 reviews)
Swallow Cottage is beautifully designed and maintained with all comforts and facilities. The location is good for country and seaside walks as well as access to Wales, Wells, Glastonbury (close to M5). The lane is only daunting the first time; all users are sensible and respectful of others. The hosts are very friendly, warm and accessible if advice or information is needed.
Meredith W.
Stayed May 2024
The Highlight of our Trip
1010 out of 10
Exceptionalexceptional
49 reviews(49 reviews)
Our stay at Acorn Cottage, Little Howle Farm has been an absolute delight. The hosts, Amanda and Derek catered for our every need and the cottage was meticulously maintained with special touches such as scones, cream and jam. The whole cottage speaks quality, with a comfy king mattress, a wonderful bathroom and comfortable living areas. It is warm and inviting with thoughtful surprises throughout the cottage. This cottage should be on your list!! Thank you again Amanda and Derek. Your attention to detail, kindness and care for us and your community is amazing!!
Brian M.
Stayed Apr 2023
Christmas stay in countryside
1010 out of 10
Exceptionalexceptional
153 reviews(153 reviews)
Wonderful week stay in this homely little barn. Liz and John were very helpful and responsive at all times. They are very thoughtful making the stay extra special. The surrounding countryside is beautiful. We would love to stay here again.
Helen K.
Stayed Dec 2019
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value