1 / 20The Old School House - Whitwell
Whitwell, Isle of Wight
Two dogs are welcome at this beautifully converted period house for five in the Isle of Wight village of Whitwell, with original features and an enclosed garden.
The Old School House is a striking period property in the heart of Whitwell, beautifully converted so that its original features sit alongside stylish, contemporary decor. It sleeps five and welcomes two dogs, and out the back an enclosed garden with a BBQ gives this dog friendly stay somewhere to unwind after the island's walking and cycling routes.
Double entrance doors open into an enclosed porch, the place to kick off walking shoes and wipe down muddy paws before the dogs go further, and the bright dining hall beyond gives an instant feel for the house's character. A light, airy single bedroom opens off it, followed by the first of two ground floor shower rooms and a staircase to the double in the eaves, whose large window overlooks the living area.
In the cosy lounge, the seating is ample and comfortable, there is a Smart TV, and the dogs will flop down here once the exploring is over. From the lounge, a second staircase reaches the king size bedroom tucked under the eaves, where large traditional windows flood the room with light. Past the lounge, the bright kitchen leads to the second shower room. Out the back, the enclosed garden has furniture and catches the morning sun, ideal for planning the day over coffee while the dogs investigate.
Whitwell has many cycling and walking routes for the dogs, and the village is famous for the oldest pub on the island, dating back to the 15th century. Ventnor, 2.5 miles away, has panoramic coastal views and fresh seafood restaurants, the pretty villages of Niton and Godshill have thatched cottages and tea rooms, and Osborne House, Blackgang Chine, The Needles, Carisbrooke Castle and Cowes are all within 15 miles.
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 £471 for 7 nights
The Old School House - Whitwell takes 2 dogs 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
- 2 dogs
- Enclosed Garden
- Yes
- Finally heading out the back of the property there is a lovely enclosed garden with garden furniture and a BBQ
- Sleeps
- 5 guests
- Rooms
- 3 bedrooms, 2 bathrooms
- Price
- from £471 / 7 nights
- Grading
- 4 star
- Arrival
- in from 16:30, out by 10:00
- Facilities
- Parking, Wifi
The Old School House - Whitwell from £471 for 7 nights
Book with holidaycottages.co.ukFrequently Asked Questions
Is The Old School House - Whitwell dog friendly?
Yes, The Old School House welcomes dogs — up to two at a time. They have the run of the entire ground floor, including a porch, lounge and kitchen, plus direct access to the enclosed garden at the back of the house.
Are dogs allowed at The Old School House - Whitwell year round?
The listing doesn't specify any seasonal restrictions on dogs, so it's worth contacting the property directly to confirm availability for your dates. Given the setup — with ground-floor access, two downstairs shower rooms and an enclosed garden — it's clearly a place designed with dogs firmly in mind.
What should I know before visiting The Old School House - Whitwell with my dog?
You can bring up to two dogs, and they're kept comfortably on the ground floor, which includes a porch, lounge, kitchen and two shower rooms — so no stairs to navigate. The enclosed garden catches the morning sun and gives dogs a safe space outside. Whitwell itself sits inland in the south of the island, with lanes and bridleways heading off in several directions, and the coast is a short drive away if you fancy a beach day.
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The Old School House - Whitwell from £471 for 7 nights
Book with holidaycottages.co.ukWhat’s Nearby?
Attraction1.7 mi awaySt Catherine's Oratory
Isle of Wight
A 14th century octagonal tower on the highest down on the Isle of Wight, built as penance for looting a shipwreck. A stiff climb with your dog to earn it.
Beach1.8 mi awaySteephill Cove (via Ventnor Botanic Garden)
Isle of Wight
One of the most picturesque small coves in England, accessible only on foot and almost unchanged for decades, with a tiny beach café and lobster pots on the quay.
Attraction1.9 mi awayAppuldurcombe House
Isle of Wight
The baroque shell of the grandest house on the Isle of Wight, with Capability Brown parkland for your dog and no roof to leave them out of.
Walk2 mi awaySt Catherine's Down and the Hoy Monument
Isle of Wight
A ridge walk for dogs above Blackgang, past the medieval Oratory to the Hoy Monument, with views along the whole length of the island.
Walk2.6 mi awaySt Boniface Down and Ventnor Downs Circular
Isle of Wight
Dogs get a proper leg-stretch up the highest ground on the Isle of Wight, past semi-wild ponies and goats, with views over Sandown Bay at the top.
Beach2.9 mi awayWheelers Bay
Isle of Wight
A small, rocky cove east of Ventnor on the warm Isle of Wight Undercliff, with year-round dog access, interesting tidal ledges to explore, and a steep approach that keeps crowds away.