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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136 cottages

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  • Sleeps 2

    1 Harrow Cottages

    Seaview

    From £356 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

    Mariners Cove

    Bembridge

    From £390 a week

    This charming one bedroom apartment forms part of a country house set around a shared Spanish-style courtyard, just outside the bustling village of Bembridge. With everything set on the ground floor, ...

  • Sleeps 2

    18 Seaview Bay

    Seaview

    From £480 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 s...

  • Sleeps 2 dogs allowed

    Grace Cottage

    4.8 miles W of Ventnor

    From £525 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 2

    19 Seaview Bay

    Seaview

    From £550 a week

    Escape to the delights of 19 Seaview Bay to enjoy a slice of stunning Island coastline, a gentle stroll around the pretty local shops, relax with an afternoon tea at Seaview Hotel or just sit with a c...

  • Sleeps 6

    Valdora

    Seaview

    From £554 a week

    Perfectly situated in the heart of the charming village of Seaview, Valdora is a gorgeous holiday retreat, beautifully styled to offer the very best in contemporary living. Seaview is the most sought-...

  • Sleeps 2

    Oceanix

    Ventnor

    From £567 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

    Buckland Cabin

    Seaview

    From £597 a week

    Tucked away just off the High Street in Seaview, this recently renovated and beautifully presented cabin is ideal if you are seeking a romantic hideaway for two. Step inside the warm and welcoming...

  • Sleeps 4

    Bay View

    Freshwater

    From £614 a week

    This beautiful contemporary apartment is literally perched above the beach, offering stunning views of the picturesque Freshwater Bay. Extremely well appointed, the apartment offers modern open plan l...

  • Sleeps 4 dogs allowed

    Escape Away

    Freshwater

    From £617 a week

    New to the Classic portfolio, very close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base yourself for a peaceful...