May Half Term Cottages

By late May the sea has warmed enough to be able to take a dip, have a surf or explore the coastline by Kayak or Paddleboard. The Isle of Wight is famous for its dramatic coastline and beaches and there’s always somewhere new to explore each time you visit.

The beaches themselves are varied, with predominantly sandy beaches along the south coast and more rocky beaches (perfect for crabbing) along the northern coast, particularly in the north east of the Island. Any budding fossil hunters will be spoilt for choice of areas to forage for hidden specimens, but the best spots are between Atherfield and Brook.

In addition to the usual tourist hot-spots such as Robin Hill, Blackgang chine, and Amazon world, we also have many areas where you can escape the crowds and enjoy the wonderful nature of the Island. 

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105 cottages

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  • Central Wight
  • Island Harbour
  • Merstone
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  • Sandown
  • Seaview
  • St Helens
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  • North Wight
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  • East Cowes
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  • Whippingham
  • South Wight
  • Godshill
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  • Ventnor
  • West Wight
  • Brighstone
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  • Yarmouth
  • Sleeps 2

    1 Harrow Cottages

    Seaview

    From £358 a week

    This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from both the front and ...

  • Sleeps 2 dogs allowed

    Oceanix

    Ventnor

    From £537 a week

    A beautifully located top floor apartment in the heart of Ventnor, Oceanix provides the perfect seaside getaway for your next Isle of Wight holiday. The property has been thoughtfully decorated thr...

  • Sleeps 2

    18 Seaview Bay

    Seaview

    From £550 a week

    Perfectly situated in the much sought-after village of Seaview on the Isle of Wight, 18 Seaview Bay is a charming, sunny apartment found in a small development, close to the village centre and just a ...

  • Sleeps 2

    Grace Cottage

    4.8 miles W of Ventnor

    From £560 a week

    This gorgeous barn conversion is set within the grounds of the stunning North Grounds Farm, just outside the village of Chale Green on the southern side of the Island. For the environmentally consciou...

  • Sleeps 6 dogs allowed

    Underwood Cabin

    5.3 miles E of Yarmouth

    From £763 a week

    Nestled next to St Hubert's Lodge surrounded by tranquil woodlands and green pastures, Underwood Cabin is a delightful rural retreat, perfectly situated on the edge of the Isle of Wight National Lands...

  • Sleeps 4 dogs allowed

    Sea Lights

    1.4 miles W of Cowes

    From £934 a week

    Situated close to the beating heart of world-famous Cowes, lies the pretty coastal village of Gurnard, where you will find this handsome coastal ground floor pet-friendly apartment, comfortably sleepi...

  • Sleeps 5

    Stargazers' Retreat

    3.6 miles W of Ventnor

    From £220 a week

    Welcome to Stargazers' Retreat, a heavenly glamping yurt nestled in rural splendour on the southerly tip of the Isle of Wight with blissful views of Reeth Bay and beyond. Situated just outside the pre...

  • Sleeps 3

    Seascape

    Ventnor

    From £486 a week

    Located in the cosmopolitan town of Ventnor within a Victorian townhouse, Seascape is a modern two-bedroom, ground floor, apartment with spectacular sea views overlooking the bay. This charming Isle o...

  • Sleeps 3 dogs allowed

    The Cattle Byre

    3.5 miles E of Brighstone

    From £588 a week

    Tucked away in a peaceful rural setting on the west side of the island, The Cattle Byre is a beautifully converted barn that blends rustic charm with modern comfort. Perfect for a relaxing countryside...

  • Sleeps 4 dogs allowed

    Berry Cabin

    Seaview

    From £365 a week

    What a little cutie! Berry Cabin is a delightful bolthole for four guests and one well behaved doggy looking for some summer fun! Surrounded by Hersey nature reserve and countryside views, it offers a...