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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115 cottages

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  • 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

    The Studio

    2.1 miles SE of Ryde

    From £372 a week

    Whether you seek relaxation or adventure on the Isle of Wight, The Studio provides the most welcoming modern-rustic retreat to experience the best of natural beauty and contemporary comforts. Perfect ...

  • Sleeps 2

    Buckland Cabin

    Seaview

    From £540 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

    Grace Cottage

    4.8 miles W of Ventnor

    From £543 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 2 dogs allowed

    Sunrise and Stars

    3.3 miles W of Ventnor

    From £85 a week

    Step into an oasis of peace and tranquility on the Isle of Wight at Sunrise and Stars, a beautifully crafted hideaway with a pool for private use and a hot tub, surrounded by captivating countryside a...

  • Sleeps 2

    18 Seaview Bay

    Seaview

    From £600 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 dogs allowed

    The Stables

    3.2 miles W of Ventnor

    From £93 a week

    Welcome to The Stables, a romantic getaway for two! Close to the seaside town of Ventnor, with its beautiful beachfront, you can explore this corner of the Island and then retreat back to your private...

  • Sleeps 6

    30 Seaview Bay

    Seaview

    From £670 a week

    If you're searching for a place to stay by the sea, 30 Seaview Bay could be just the spot. Perched just steps away from the enchanting Seagrove Bay and Seaview Bay, this sunny apartment really is a wo...

  • Sleeps 4 dogs allowed

    Daisy Cottage

    Bembridge

    From £672 a week

    Daisy Cottage is a lovely cosy and welcoming mid terrace cottage nestled in the heart of Bembridge. Located in one of the most desirable areas to live in on the Isle of Wight, this delightful cottage ...