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

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Where:
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Add Room / Unit

Isle of Wight self catering

Number of results:

Number of results: 259

, currently showing 41 to 60.

  1. Add Sainham Farm Holiday Cottages to your Itinerary

    Sainham Farm Holiday Cottages

    Type

    Type:

    Self-Catering

    Godshill, VENTNOR

    Situated on a delightful farm in a lovely part of the island, these charming cottages rest in an Isle of Wight National Landscape (formerly known as Area of Outstanding Natural Beauty) between Appuldurcombe Down and the picturesque village of…

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  2. Add Salty Holidays to your Itinerary

    Tourism For All

    Self-Assessed Accessibility Information

    Salty Holidays

    Type

    Type:

    Self-Catering

    Ventnor

    Enjoy stunning sea views from our 5 well equipped and spacious self-catering apartments. With private parking, we are close to the beach and in the best location to explore beautiful Ventnor.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  3. Add Santa Maria to your Itinerary

    Santa Maria

    Type

    Type:

    Self-Catering

    HAVENSTREET

    A well-presented semi-detached bungalow situated in the beautiful rural village of Havenstreet, just outside Ryde on the Isle of Wight.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  4. Add Red Butt to your Itinerary

    Red Butt

    Type

    Type:

    Self-Catering

    FRESHWATER

    This recently refurbished 3 bedroom Victorian house is situated in Freshwater, Isle of Wight.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  5. Add Tiny Homes Holidays to your Itinerary

    Tourism For All

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    Tiny Homes Holidays

    Type

    Type:

    Self-Catering

    NORTHWOOD

    Tiny Homes Holidays is a unique Tiny House hamlet providing one of the best in greener holidays.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  6. Add Newbarn Country Cottages - Parlour Cottage, Dairy Cottage, Stable Cottage & The Old Brewhouse to your Itinerary

    Tourism For All

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    Newbarn Country Cottages - Parlour Cottage, Dairy Cottage, Stable Cottage & The Old Brewhouse

    Type

    Type:

    Self-Catering

    GATCOMBE

    Three beautiful conversions in secluded downland valley in centre of Island.

    Dates

    From:
    1 Jan 2026to31 Dec 2026

    Gradings

    • 4 Visit England Stars Self Catering
    4 Visit England Stars Self Catering
  7. Add No 1 Sovereign's Gate Osborne to your Itinerary

    No 1 Sovereign's Gate Osborne

    Type

    Type:

    Self-Catering

    EAST COWES

    Nos 1 Sovereign's Gate Osborne is a holiday cottages that has been developed in this iconic building at Osborne. Sovereign's Gate was commissioned by Queen Victoria and Prince Albert as the formal entrance to Osborne.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  8. Add Little Halt to your Itinerary

    Little Halt

    Type

    Type:

    Self-Catering

    FRESHWATER

    This picturesque thatched cottage is very attractively situated, in peaceful surroundings overlooking Pound Green, on the outskirts of Freshwater.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  9. Add Little Parklands Holiday Apartments to your Itinerary

    Little Parklands Holiday Apartments

    Type

    Type:

    Self-Catering

    SANDOWN

    Karen and Peter Hudson welcome you at their three spotlessly clean and attractively furnished self catering holiday apartments in Sandown on the Isle of Wight.

    The apartments are situated in a quiet position within walking distance of Sandown…

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  10. Add Longwood Edge to your Itinerary

    Tourism For All

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    Longwood Edge

    Type

    Type:

    Self-Catering

    VENTNOR

    Beautiful detached cabin style bungalow with stunning sea views. Situated in the much sought after hamlet of Bonchurch, Longwood Edge is 150 yards away from the ever popular Bonchurch Inn.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  11. Add Lyon Court - The Garret & The Old Stable to your Itinerary

    Lyon Court - The Garret & The Old Stable

    Type

    Type:

    Self-Catering

    SHANKLIN

    Lyon Court is a beautiful country house in Shanklin (10 mins walk to old village and shops, 15 mins walk to Shanklin beaches) that has been converted into apartments offering self catering accommodation.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  12. Add Marina View to your Itinerary

    Marina View

    Type

    Type:

    Self-Catering

    EAST COWES

    Modern 3 bed holiday home situated in East Cowes Marina

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  13. Add Mermaid Holidays to your Itinerary

    Mermaid Holidays

    Type

    Type:

    Self-Catering

    VENTNOR

    At Mermaid Holidays, we believe in doing things differently. After all, you're not looking for just another getaway—you're after something extraordinary. Why settle for the usual when you can experience a stay that's as unique as you are?

    Dates

  14. Add Middle Barn Farm to your Itinerary

    Middle Barn Farm

    Type

    Type:

    Self-Catering

    SANDOWN

    Two beautifully presented and charming countryside cottages set in the heart of the Arreton Valley.

    Dates

    From:
    1 Apr 2026to31 Oct 2026
  15. Add Moor Farm Holiday Cottages to your Itinerary

    Tourism For All

    Self-Assessed Accessibility Information

    Moor Farm Holiday Cottages

    Type

    Type:

    Self-Catering

    GODSHILL

    We have four beautifully restored barn conversions located within Moor farm, set in idyllic countryside only 1/2 mile from the picturesque village of Godshill.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  16. Add No 2 Sovereign's Gate Osborne to your Itinerary

    No 2 Sovereign's Gate Osborne

    Type

    Type:

    Self-Catering

    EAST COWES

    Nos 2 Sovereign's Gate Osborne is a holiday cottages that has been developed in this iconic building at Osborne. Sovereign's Gate was commissioned by Queen Victoria and Prince Albert as the formal entrance to Osborne.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  17. Add National Trust Chert and Little Chert Holiday Cottages to your Itinerary

    National Trust Chert and Little Chert Holiday Cottages

    Type

    Type:

    Self-Catering

    VENTNOR

    National Trust Chert and Little Chert self-catering holiday cottages are distinctive and quirky 1970s houses less than a mile from the sea.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  18. Add Yar Quay to your Itinerary

    Yar Quay

    Type

    Type:

    Self-Catering

    ST HELENS

    Yar Quay is a charming 3 storey house backing onto the River Yar in St Helens. This self catering house provides a tranquil place to stay to explore the Isle of Wight with stunning views of the marina, marshes and countryside. 

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  19. Add National Trust Needles Coastguard Cottages to your Itinerary

    National Trust Needles Coastguard Cottages

    Type

    Type:

    Self-Catering

    Needles Headland

    A pair of former Coastguard Cottages, named after notable shipwrecks and situated in a stunning position height up on the Needles Headland with spectacular views of the Solent and surrounding areas. 

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  20. Add National Trust Old Church Lodge Holiday Cottage to your Itinerary

    National Trust Old Church Lodge Holiday Cottage

    Type

    Type:

    Self-Catering

    ST HELENS

    Old Church Lodge, a two bedroom Victorian cottage sleeping four, is the perfect place to explore the East of the Isle of Wight.

    Dates

    From:
    1 Jan 2026to31 Dec 2026

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