Imagined illustration of decorated Christmas trees in a village hall, with festival dates and original Isle of Wight Stays logo. Not a photograph of a festival venue.

Plan a December Break for Brighstone Christmas Tree Festival 2026

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A little Christmas sparkle for your island break! Brighstone Christmas Tree Festival returns on 3–6 December 2026 across Brighstone, Mottistone and nearby venues. Entry is free, with donations welcomed. Check venue opening times with the organiser. Plan your stay at www.iowstays.co.uk. Book accommodation direct and ferry discount links are automatically sent by email. Please like and share with a Christmas-loving friend. Picture: illustration.

Illustration of a red squirrel in autumn woodland with the original Isle of Wight Stays shield logo. Not a documentary photograph.

A Wilder November Island Break: Discover Borthwood Copse

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Planning a November island escape? Make time for Borthwood Copse near Winford. The National Trust’s red-squirrel walk is 1.2 miles, with around 45 minutes suggested. Look up into the branches, but remember sightings are never guaranteed. Paths can be muddy and uneven. Plan your stay at www.iowstays.co.uk. Please like and share with a nature-loving friend. Picture: illustration.

Illustrated festive steam train scene with Santa Specials dates for December 2026 and the original Isle of Wight Stays logo. Imagined scene, not a photograph of Havenstreet.

Plan a Christmas Island Break for Santa Specials 2026

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All aboard for a Christmas island break! The Isle of Wight Steam Railway’s Santa Specials run at Havenstreet on 12–13 and 19–24 December 2026. Check train times and tickets with the railway before planning your stay. Book accommodation direct at www.iowstays.co.uk and ferry discount links are automatically sent by email. Please like and share with a Christmas-loving friend. Picture: illustration.

Genuine photograph of Island Retreat's twin bedroom in a teal and gold frame with the original Isle of Wight Stays shield logo.

Island Retreat: plan your next Sandown break

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Planning your next Isle of Wight break? Meet Island Retreat at Fairway Holiday Park in Sandown.

A self-catering base with a fully equipped kitchen, Smart TV, free WiFi and parking beside the caravan. Dogs are welcome for an additional fee.

Book accommodation directly with Isle of Wight Stays and ferry discount links are automatically sent by email.

Explore the property and check dates at www.iowstays.co.uk/island-retreat/

Please like and share this with someone planning an island break.

Illustrated festive gift stalls promoting Northwood House Christmas Fair in Cowes on 28 and 29 November 2026

Plan a November Break for Northwood House Christmas Fair 2026

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Christmas shopping with an island escape? Northwood House Christmas Fair in Cowes is free to enter on 28 and 29 November 2026, 10am to 4.30pm. Plan your stay at www.iowstays.co.uk. Book direct and ferry discount links arrive automatically by email. Please like and share with a Christmas-loving friend. Picture: illustration.

Illustrated ferry and coastal town with walking boots and luggage, promoting a car-free Isle of Wight break in November and December 2026

Plan a Car-Free Isle of Wight Break for November or December 2026

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Planning a car-free November or December island break? Compare ferry fares and onward connections. Our guide covers Wightlink’s published winter fare example and the council’s transport plans. Book accommodation direct and ferry discount links arrive automatically by email. Plan your stay at www.iowstays.co.uk. Please like and share with an island-loving friend. Picture: illustration.

Illustrated Christmas pantomime stage with a fairytale mirror and apple, promoting Medina Theatre's selected December 2026 dates

Plan a Christmas Panto Break: Medina Theatre 2026

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Snow White and the Seven Dwarfs comes to Medina Theatre, Newport, on selected dates from 19 to 30 December 2026. Plan your stay at https://www.iowstays.co.uk. Book direct and ferry discount links arrive automatically by email. Please like and share with someone planning a Christmas island break. Picture: illustration.

Island Bordeaux three-bedroom holiday lodge with private decking in Sandown, Isle of Wight

Island Bordeaux: A Spacious Sandown Escape for Six

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Looking for a spacious Isle of Wight escape? Island Bordeaux is a three-bedroom lodge for up to six guests, with private decking, parking beside the accommodation, Wi-Fi and an en-suite. Book direct and ferry discount links are sent automatically by email. Check availability at www.iowstays.co.uk/island-bordeaux/

Illustration of a festive Christmas fair at Colwell Common with the original Isle of Wight Stays shield logo.

Plan Ahead for Totland Christmas Fair 2026

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Planning a festive Isle of Wight break? Totland Christmas Fair takes place at Colwell Common on Friday 27 November 2026, from 1.30pm to 6pm. Book accommodation directly with Isle of Wight Stays and automatically receive ferry discount links by email. Plan your stay at www.iowstays.co.uk. Picture: illustration.

Illustration inspired by Osborne House in autumn with the original Isle of Wight Stays shield logo.

Plan a Royal Winter Break: Osborne in November and December 2026

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Planning a November or December 2026 island break? Visit Osborne. From 7 November to 23 December, the ground floor and grounds open Wednesday to Sunday, 10am to 4pm. Last entry 3pm. Check English Heritage’s latest details before travelling. Book accommodation directly with Isle of Wight Stays and automatically receive ferry discount links by email. Check accommodation dates at www.iowstays.co.uk. Picture: illustration.

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