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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166 cottages

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  • Sleeps 2

    The Battenburg Studio


    From £280 a week

    This contemporary studio apartment enjoys a great location in Shanklin. With modern decor and open plan living, it makes a cosy retreat for a couple looking for a coastal break. There's easy acces...

  • Sleeps 2

    The Beatrice Studio


    From £280 a week

    Located on the first floor of Shanklin Villa, a lovely Victorian property, this small studio apartment packs a punch despite its size. Enjoying beautiful sea views from its elevated position, The Beat...

  • Sleeps 2

    Mariners Cove


    From £292 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. You can enjoy the evenings at Marine...

  • Sleeps 2

    Berryl Mead View

    2.7 miles W of Ventnor

    From £293 a week

    Located in a rural village setting, Berryl Mead View is a delightful home from home cottage with plenty of space. It is well-equipped throughout and has an extremely comfortable living-room with Sky T...

  • Sleeps 2

    1 Harrow Cottages


    From £300 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

    Grace Cottage

    4.8 miles W of Ventnor

    From £356 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

    Little Barn Retreat

    1.2 miles E of Newport

    From £387 a week

    This absolutely gorgeous barn conversion is the perfect place for a couple's holiday, located on the Durton Farm Estate in the centre of the Island. Lovingly refurbished by the owner, Little Barn Retr...

  • Sleeps 2

    The Cadogan Apartment


    From £415 a week

    Sitting within a beautifully converted Victorian villa, The Cadogan Apartment offers a high standard of accommodation for a couple or lone traveller looking for a coastal break. Guests staying at this...

  • Sleeps 2

    Buckland Cabin


    From £538 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 2 dogs allowed



    From £600 a week

    Just a few minutes' walk from idyllic Freshwater Bay, Temperance is a real gem. A stylish and spacious first floor apartment, unwind into blissful island life where just a short walk will take you to ...