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166 cottages

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  • Sleeps 6

    4 Landfall House

    Seaview

    From £700 a week

    Situated just a few steps from the beach, this ground floor apartment makes the most of its location with both the sitting-room and kitchen/diner to the front boasting wonderful sea views. 4 Landfall ...

  • Sleeps 6 dogs allowed

    The Shute

    1.8 miles W of Ventnor

    From £715 a week

    This gorgeous cottage, set in the breathtaking location of St Lawrence, has a large patio and unrivalled sea views. A truly magical place to sit and enjoy the scenery, the seaward facing conservatory ...

  • Sleeps 6

    Oak Tree Cottage

    Seaview

    From £722 a week

    With a stunning spacious sea facing balcony, Oak Tree Cottage is in a superb location just steps from the beach and a short walk along the seafront into Seaview Village. An outdoor dining-table and ga...

  • Sleeps 6 dogs allowed

    The Haven

    St Helens

    From £746 a week

    A simply gorgeous three bedroom property just off St Helens' green on the eastern side of the Isle of Wight, The Haven is just a short walk from the coast and a ten minute stroll takes you to St Helen...

  • Sleeps 6 dogs allowed

    Merivale

    Seaview

    From £750 a week

    This lovely, light and spacious detached house located on Fairy Road in Seaview, just a short stroll from the seafront, makes a fantastic base for a wonderful holiday on the Isle of Wight. This exclus...

  • Sleeps 6

    Sunset Cottage

    5.5 miles W of Ventnor

    From £815 a week

    Set in the grounds of the impressive Pyle Manor, this newly refurbished cottage offers a wonderful base on the Isle of Wight with the shared use of an outdoor unheated swimming pool (available between...

  • Sleeps 6

    The Tap Room

    Freshwater

    From £850 a week

    If you are looking for that very special holiday in a truly unique location, then The Tap Room at Golden Hill Fort is for you. New to the Classic Cottage portfolio in 2021 the panoramic views from the...

  • Sleeps 6

    Raleigh Cottage

    Seaview

    From £850 a week

    In a quiet position within a secluded courtyard in the village of Seaview, Raleigh Cottage is the perfect blend of old-world charm and contemporary comfort. It would suit a family or friends travellin...

  • Sleeps 6

    The Lodge

    Ryde

    From £1007 a week

    This absolutely stunning property is laid over five mezzanine floors, has two sea-facing balconies and a hot tub with a sea view! Beautifully decorated throughout, The Lodge offers guests the perf...

  • Sleeps 6

    9 The Ruskins

    Bembridge

    From £1045 a week

    This delightful family holiday home can be found just a short stroll from the beautiful beaches of Bembridge and a wonderful array of traditional shops and restaurants. Light filled and with oodles of...