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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Add Room / Unit

Isle of Wight self catering

Number of results:

Number of results: 260

, currently showing 41 to 60.

  1. 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
  2. Add Clarence House Holiday Apartments to your Itinerary

    Clarence House Holiday Apartments

    Type

    Type:

    Self-Catering

    VENTNOR

    4 luxurious "Boutique Styled" holiday apartments in the heart of Ventnor with stunning views over Ventnor Park

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  3. Add The Coach House Shanklin to your Itinerary

    Tourism For All

    Self-Assessed Accessibility Information

    The Coach House Shanklin

    Type

    Type:

    Self-Catering

    SHANKLIN

    Charming comfortable stone cottage, sleeping 6 people, on the edge of Shanklin Old Village and close to shops, pubs, restaurants and the beach.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  4. 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
  5. Add Yafford Mill Barn to your Itinerary

    Yafford Mill Barn

    Type

    Type:

    Self-Catering

    SHORWELL

    Yafford Mill Barn is nestled within the beautiful countryside of the South West of the Island.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  6. Add Moor Farm Holiday Cottages to your Itinerary

    Tourism For All

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    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
  7. Add Nettlecombe Farm to your Itinerary

    Tourism For All

    Self-Assessed Accessibility Information

    Nettlecombe Farm

    Type

    Type:

    Self-Catering

    Whitwell

    Award-winning, dog friendly, luxurious self-catering cottages, sleeping between 3-10, fishing lakes, unique farm feeding tours, free car charging and discounted ferries, we guarantee your family the holiday of a lifetime.
    Immerse yourself in the…

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  8. Add Whitwell Station Holiday Homes to your Itinerary

    Whitwell Station Holiday Homes

    Type

    Type:

    Self-Catering

    Whitwell, VENTNOR

    Whitwell Station sits on the former Newport, Godshill & St Lawrence Railway line. Set in nearly 2 acres, overlooking the beautiful village of Whitwell it has commanding views over the southern downs – an Isle of Wight National Landscape (formerly…

    Dates

    From:
    29 Mar 2026to31 Oct 2026
  9. Add Brambles Farm Bungalow to your Itinerary

    Brambles Farm Bungalow

    Type

    Type:

    Self-Catering

    FRESHWATER

    Brambles Farm Bungalow is located in the West Wight, a beautiful part of the Island, with miles of heritage coastline, scenic walks, cycle tracks and breathtaking views from Tennyson Down, Headon Warren and The Needles.

    Dates

    From:
    15 Feb 2026to15 Nov 2026
  10. Add New Bank End Farm to your Itinerary

    New Bank End Farm

    Type

    Type:

    Self-Catering

    VENTNOR

    Hidden on the south coast of the Island, in an idylic location with fantastic sea views

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  11. Add Arethusa Cottage Holiday Lodges to your Itinerary

    Arethusa Cottage Holiday Lodges

    Type

    Type:

    Alternative Accommodation

    Ryde

    Arethusa Cottage Holiday Lodges boasts two very different style self-catering lodges. Both are very comfortable and well equipped and suitable for families, couples or groups of friends.

    Dates

    From:
    1 Jan 2026to31 Dec 2026

    Gradings

    • Visitor Ready Accredited by VisitEngland
    Visitor Ready Accredited by VisitEngland
  12. Add Borthwood Cottages to your Itinerary

    Tourism For All

    Self-Assessed Accessibility Information

    Borthwood Cottages

    Type

    Type:

    Self-Catering

    Sandown

    Tucked away in a tranquil rural setting, Borthwood Cottages offer an idyllic escape. Cottages sleep between four and six guests. All four cottages are accessible and dog friendly.

    Dates

    From:
    1 Jan 2026to31 Dec 2026

    Gradings

    • 4 Visit England Stars Self Catering
    4 Visit England Stars Self Catering
  13. Add Lisle Combe Cottage to your Itinerary

    Lisle Combe Cottage

    Type

    Type:

    Self-Catering

    St Lawrence, VENTNOR

    Self catering cottage sleeping up to 6 people on the south coast of the Island with spectacular sea views.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  14. Add The Coach House at Ivy Hall to your Itinerary

    The Coach House at Ivy Hall

    Type

    Type:

    Self-Catering

    WOOTTON

    The Coach House at Ivy Hall is open all year. There are lots of lovely walks nearby and is situated on the Coastal Walk. Wootton Creek and The Lake are 1 minute walk with all sorts of wildlife including the occasional seal.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  15. Add Clarence House Holiday Apartments and Rooms (formerly The Ivy Apartments) to your Itinerary

    Clarence House Holiday Apartments and Rooms (formerly The Ivy Apartments)

    Type

    Type:

    Self-Catering

    SHANKLIN

    These family friendly apartments are ideally located near beaches, shops, amusements and all amenities including the Railway Station.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  16. Add Sea Shells by the Beach to your Itinerary

    Sea Shells by the Beach

    Type

    Type:

    Self-Catering

    BONCHURCH

    Luxury seafront 5 star self-catering holiday cottage in beautiful Bonchurch.

    Dates

    From:
    1 Feb 2026to31 Dec 2026
  17. Add Tiny Homes Holidays to your Itinerary

    Tourism For All

    Self-Assessed Accessibility Information

    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
  18. Add Island Bell Tents to your Itinerary

    Island Bell Tents

    Type

    Type:

    Glamping

    ISLANDWIDE

    Luxury Bell Tent Hire across the Isle of Wight. All of the fun with none of the hassle! 5m bell tents can sleep 5 people comfortably. Dogs accepted in dedicated tents.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  19. 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
  20. Add Island Riding Centre - Self Catering Cottages & Safari Tents to your Itinerary

    Tourism For All

    Self-Assessed Accessibility Information

    Island Riding Centre - Self Catering Cottages & Safari Tents

    Type

    Type:

    Self-Catering

    Newport

    Our modern and bright self-catering accommodation is set across a range of cottages, a Victorian Dairy barn conversion, a detached modern ranch style-bungalow and gated safari camp, we have been awarded 4* Rosette awarded by Visit England for our…

    Dates

    From:
    1 Jan 2026to31 Dec 2026

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