1 / 24The Old School House - Earlswood
Earlswood, Monmouthshire
A traditional stone former schoolhouse for four in the Monmouthshire hamlet of Earlswood, with an enclosed garden at the rear, a wood burner, paths from the door and one dog welcome.
The Old School House is a traditional stone cottage in the peaceful hamlet of Earlswood, set within the Wye Valley to the west of Chepstow. Once the local schoolhouse, it now gives four guests and their dog a warm, dog friendly welcome, with an enclosed garden at the rear and well waymarked paths leading off from the front door.
Just inside there is space to leave muddy boots and coats behind, and from the entrance the way leads into the kitchen and diner, traditional in style, where everyone gathers for a hearty supper after a day out with the dog. A Nespresso machine sees to the mornings. In the lounge, a wood burner glows and there is a Smart TV for a good film, and the dog curls up by the fire while it plays.
When the day is done the stairs lead up to three bedrooms: one super king that unzips into a twin on request, a double and a single. Outside, the enclosed garden behind the house holds a table, chairs and a charcoal barbecue, so supper can move out there while the dog explores. Cyclists have a bike store for four with Sold Secure Gold anchor points, and National Cycling Route 42 runs right past the house.
Walkers and their dogs can set out on foot from the door, and the paths include Wentwood, the largest ancient woodland in Wales. Chepstow has a good choice of pubs and restaurants and a castle that is the oldest surviving post Roman stone fortification in Britain. Heritage runs deep around here too: Goodrich, Monmouth and Raglan castles, the ancient Kilgwrrwg church and the remains of Tintern Abbey are all within a short drive.
We research every description carefully and believe it to be accurate, but details can change. Please confirm anything important, especially dog rules, with the booking agent or property owner before you book.
Book your stay
from £668 for 7 nights
The Old School House - Earlswood takes 1 dog and is booked through holidaycottages.co.uk.
Book with holidaycottages.co.ukPrices are a guide only, checked 27 August 2026, and change with dates and availability. We may earn a commission if you book through this link, at no extra cost to you.
At a Glance
- Dogs Welcome
- 1 dog
- Enclosed Garden
- Yes
- Enclosed garden with charcoal BBQ (bring your own charcoal) | Off-road parking for 2 cars | Fast broadband if you need to work from home | Ev charging available | Bike store for four bikes with Sold S
- Sleeps
- 4 guests
- Rooms
- 3 bedrooms, 1 bathroom
- Price
- from £668 / 7 nights
- Grading
- 4 star
- Arrival
- in from 16:00, out by 10:00
- Facilities
- Bbq, Ev charging, Open fire, Parking, Wifi
The Old School House - Earlswood from £668 for 7 nights
Book with holidaycottages.co.ukFrequently Asked Questions
Is The Old School House - Earlswood dog friendly?
Yes, The Old School House welcomes one dog per booking. The property has been set up with dogs genuinely in mind — there's a dedicated boot room just inside the entrance where your dog comes back in after walks, keeping muddy paws well away from the kitchen and living spaces.
Are dogs allowed at The Old School House - Earlswood year round?
The listing doesn't specify any seasonal restrictions on dogs, so it's worth checking directly with the owner when you book to confirm availability for your dates. Given the wood burner, enclosed garden and proximity to Wentwood, it's a place that lends itself to a visit in any season.
What should I know before visiting The Old School House - Earlswood with my dog?
The booking allows one dog, so if you're travelling with more than one it's worth checking with the owner in advance. The enclosed garden is small enough that your dog will likely treat it as a patrol route rather than a run, but Wentwood — the largest ancient woodland in Wales — begins within walking distance and offers enough waymarked trails for a different loop every day of a week-long stay.
Visitor Reviews
No reviews yet. Be the first to share your experience.
The Old School House - Earlswood from £668 for 7 nights
Book with holidaycottages.co.ukWhat’s Nearby?
Walk6.1 mi awayTintern Abbey and the Wye Valley Walk
Monmouthshire
A classic dog friendly Wye Valley loop from Tintern Abbey up through ancient woodland to the Devils Pulpit viewpoint, returning along the river.
Walk6.4 mi awayWye Valley: Brockweir to Bigsweir Bridge
Monmouthshire
A quiet dog friendly Wye Valley loop along Offa's Dyke and the riverbank between two historic crossings of the Wye.
Walk8.7 mi awayRaglan Castle and the River Usk Walk
Monmouthshire
An easy dog friendly walk linking the spectacular ruins of Raglan Castle with the gentle riverbank meadows and woods of the River Usk.
Walk11 mi awayPontypool Park and the Folly Tower
Torfaen
A landscaped park with an Italian garden and Shell Grotto where dogs roam off lead in the open grassland, linked by footpath to the hilltop Folly Tower.
Walk11.7 mi awayPuzzlewood and Perrygrove Woodland Walk
Gloucestershire
A short atmospheric woodland walk near the famous Puzzlewood attraction, with mossy paths and an almost fairy-tale feel.
Walk12 mi awayBlaise Castle Estate And Kings Weston Downs Loop
Somerset
A broad loop through mature woodland and the wider landscape of Kings Weston Downs, starting close to the estate entrance.