Outside view of Flackstead with the sun setting behind, property with Classic Cottages, Isle of Wight, self catering, accommodation, luxury, cottages

Classic Cottages

For over 45 years, Classic Cottages have been the independent holiday cottage and glamping specialists. Still run and owned by the founding family, we pride ourselves on our local expertise in our…

Outside view of Rosemullion, Isle of Wight, HB Holiday Lettings, coastal escape, self catering cottages and houses

HB Holiday Lettings

HB Holiday Lettings is a local, independent company offering quality holiday homes in Bembridge, St Helens and Seaview. Known for excellent customer service and over 60 five-star Google reviews, we…

Isle of Wight, Accommodation, Self Catering, Luccombe Villa, Pool

Luccombe Villa Holiday Apartments

Luccombe Villa has nine self catering holiday apartments. An elegant stone-built Victorian house standing in large secluded gardens, with outdoor swimming pool. It occupies a marvellous position…

Chale Bay Farm with sea views in the background, self catering, apartments, Isle of Wight

Chale Bay Farm

Chale Bay Farm in Chale on the Isle of Wight provides a suite of contemporary five-star luxury holiday apartments set in 26 acres, built around a courtyard with pond and water garden. Situated on the…

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Search Self-Catering

Type:
Where:
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Arrival Date:
Add Room / Unit

Isle of Wight self catering

Number of results:

Number of results: 260

, currently showing 221 to 240.

  1. Add Kemphill Granary to your Itinerary

    Kemphill Granary

    Type

    Type:

    Self-Catering

    RYDE

    5 Star barn conversion on working farm. Five bedrooms, all with ensuite bathrooms, fabulous exposed beams, floor to ceiling windows and large patio area. Open plan kitchen, lounge and dining area, sleeps 10 comfortably. Only 10 min drive from the…

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  2. Add Kenmare Cottage to your Itinerary

    Kenmare Cottage

    Type

    Type:

    Self-Catering

    SHANKLIN

    Kenmare Cottage is a semi-detached period family home perfectly located to enjoy Shanklin’s beaches, the town and quaint Old Village.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  3. Add Greystone Cottage to your Itinerary

    Greystone Cottage

    Type

    Type:

    Self-Catering

    BROOK

    Greystone Cottage is a much sought after beachside property within walking distance to Compton Bay. The cottage is set within an Isle of Wight National Landscape (formerly known as Area of Outstanding Natural Beauty) and has panoramic views of the…

    Dates

    From:
    1 Jan 2025to31 Dec 2026
  4. Add Kings Manor Farm to your Itinerary

    Kings Manor Farm

    Type

    Type:

    Self-Catering

    FRESHWATER

    A choice of four spacious and comfortable self-catering holiday cottages, located within the rural grounds of Kings Manor Farm on the Isle of Wight.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  5. Add Woodland Cottage - Fort Victoria to your Itinerary

    Woodland Cottage - Fort Victoria

    Type

    Type:

    Self-Catering

    Norton, YARMOUTH

    With amazing uninterrupted views over the sea in front, this cottage is a wonderful base for family or friends to explore this beautiful, unspoilt part of the island.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  6. Add Little Upton Barns to your Itinerary

    Little Upton Barns

    Type

    Type:

    Self-Catering

    RYDE

    Little Upton Farm has three stunning self-catering barn conversions sleeping up to 16 guests comfortably, in Ashey, close to Ryde on the North East coast of the Isle of Wight.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  7. Add Warren Hill Camp to your Itinerary

    Warren Hill Camp

    Type

    Type:

    Glamping

    Ventnor

    Warren Hill Camp is an idyllic and tranquil family-run glamping site nestled in the heart of the stunning Isle of Wight countryside. Located on a picturesque former dairy farm, it offers you the perfect opportunity to unwind, relax, and reconnect…

    Dates

    From:
    1 May 2026to30 Sept 2026
  8. Add Bodwen Corner Cottage to your Itinerary

    Bodwen Corner Cottage

    Type

    Type:

    Self-Catering

    Wootton

    Bodwen Corner is the converted old kitchens of a Victorian House, formally the residence of Countess Cowely. It is part of a larger house which has been divided. It is a quiet retreat, set in a nine-acre estate, giving guests staying here access to…

    Dates

  9. Add The Wight Holiday Company to your Itinerary

    The Wight Holiday Company

    Type

    Type:

    Self-Catering

    ISLANDWIDE

    As a small team we, at The Wight Holiday Company, can offer you the personal touch when it comes to helping you find the perfect self catering accommodation for your getaway to the Isle of Wight.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  10. Add National Trust Mottistone Manor Farmhouse Holiday Cottage to your Itinerary

    National Trust Mottistone Manor Farmhouse Holiday Cottage

    Type

    Type:

    Self-Catering

    MOTTISTONE

    A large farmhouse cottage, Mottistone Manor Farmhouse, sleeps 14 and is set in a delightful location with views over the fields to the sea. 

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  11. Add India Cottage to your Itinerary

    India Cottage

    Type

    Type:

    Self-Catering

    Ventnor

    A comfortable and cosy Grade 2 listed cottage, with private off-street parking, just a couple of minutes’ walk from Ventnor town centre and around ten minutes to Ventnor's sand and shingle beach. The cottage is ideally placed as a base to explore…

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  12. Add Cornerstone Apartments to your Itinerary

    Cornerstone Apartments

    Type

    Type:

    Self-Catering

    VENTNOR

    Cornerstone Garden Apartments are part of a very grand Victorian house. Walking distance to Ventnor and Bonchurch and beaches. Access to garden, BBQ. Ideal for families and couples. Dog walkers welcome. Seaviews from garden. Off road parking.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  13. Add Chestnut Mews Holiday Cottages to your Itinerary

    Chestnut Mews Holiday Cottages

    Type

    Type:

    Self-Catering

    SHANKLIN

    Honeysuckle, Jasmine and Clematis cottages, all have three bedrooms, sleeping up to 6, and are located on the edge of Shanklin Old Village. Only ten-minute's walk to the beach, minutes from parks, footpaths, an ideal location to explore!

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  14. Add Northcourt Manor to your Itinerary

    Northcourt Manor

    Type

    Type:

    Self-Catering

    SHORWELL

    Step into the charm of Northcourt House, a beautifully restored 17th-century Jacobean manor offering flexible group accommodation in the heart of the Isle of Wight National Landscape.

    Set within 15 acres of outstanding gardens, Northcourt is…

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  15. Add Stag Cottage to your Itinerary

    Stag Cottage

    Type

    Type:

    Self-Catering

    Godshill, VENTNOR

    This gorgeous barn conversion in Godshill offers bright accommodation in a picturesque rural setting with plenty of walks and trails for exploring the stunning countryside.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  16. Add The Lighthouse to your Itinerary

    The Lighthouse

    Type

    Type:

    Self-Catering

    VENTNOR

    The Lighthouse is a one off property with the wow factor, right on the beach at Steephill Cove. The whole house boasting exceptional sea and coastal views.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  17. Add St Davids to your Itinerary

    St Davids

    Type

    Type:

    Self-Catering

    YARMOUTH

    Luxury self-catering property with coastal views, situated on the outskirts of Yarmouth.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  18. Add House on the Shore to your Itinerary

    House on the Shore

    Type

    Type:

    Self-Catering

    YARMOUTH

    This 3 bedroom family home accommodates six adults, two children and has a small bed for a toddler and a travel cot for an infant if required. 

    With a stunning panoramic sea view across to the mainland, the house is adjacent to the coastal path as…

    Dates

    From:
    1 Mar 2026to1 Dec 2026
  19. Add Bucks Farm Holiday Cottages to your Itinerary

    Bucks Farm Holiday Cottages

    Type

    Type:

    Self-Catering

    Shorwell, Newport

    Each of our 3 cottages is thoughtfully designed to blend rustic charm with contemporary amenities.

    Dates

  20. Add The Pink Door Holiday Seaside Holiday Home to your Itinerary

    The Pink Door Holiday Seaside Holiday Home

    Type

    Type:

    Self-Catering

    VENTNOR

    Beautiful Seaside Holiday Home located on the door step of Ventnor and Bonchurch.

    Dates

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