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…

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…

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…

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Search Self-Catering

Type:
Where:
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Isle of Wight self catering

Number of results:

Number of results: 263

, currently showing 221 to 240.

  1. 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
  2. Add Hill Farm to your Itinerary

    Hill Farm

    Type

    Type:

    Self-Catering

    SANDOWN

    Two converted barns both commanding fantastic views over large areas of the eastern part of the Island. 1.5 miles to St. Helens beach and corner shop, restaurants etc. 

    Dates

    From:
    4 Apr 2026to1 Nov 2026
    From:
    2 Nov 2026to3 Apr 2027
  3. Add Chilton Farm Cottages to your Itinerary

    Chilton Farm Cottages

    Type

    Type:

    Self-Catering

    BRIGHSTONE

    Chilton Farm has eight cottages on a family working farm located in beautiful countryside and only half a mile from the sea.

    Dates

    From:
    18 Mar 2026to5 Nov 2026
  4. 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
  5. Add Rowborough Cottage to your Itinerary

    Rowborough Cottage

    Type

    Type:

    Self-Catering

    Shorwell, Newport

    Rowborough Cottage is a stylish and relaxing country cottage within a rural location with countryside views

    Dates

  6. Add Hambrough House to your Itinerary

    Hambrough House

    Type

    Type:

    Self-Catering

    Ventnor

    The two apartments at Hambrough House are located just a short walk from the centre of Ventnor, the Esplanade and the beach. 

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  7. Add The Severals to your Itinerary

    The Severals

    Type

    Type:

    Self-Catering

    SHANKLIN

    The Severals is very spacious four bedroom detached house in Shanklin, situated in a peaceful location, just a 15 minute walk to Shanklin’s lovely beaches and one minute away from a bridleway leading to scenic country walks.

    Dates

  8. 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
  9. Add Newbarn Country Cottages - Parlour Cottage, Dairy Cottage, Stable Cottage & The Old Brewhouse to your Itinerary

    Tourism For All

    Self-Assessed Accessibility Information

    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
  10. 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
  11. Add Sunset Beach to your Itinerary

    Sunset Beach

    Type

    Type:

    Self-Catering

    Freshwater

    A Renovated 3 bed detached house only 3 houses from the beach and beautiful sunsets. LOW deposits and discounted ferry travel available. We are in a perfect location for the beach and coastal walks. 

    Dates

    From:
    1 Apr 2026to31 Oct 2026
    From:
    1 Nov 2026to31 Mar 2027
  12. Add National Trust Knowles Farm Holiday Cottage to your Itinerary

    National Trust Knowles Farm Holiday Cottage

    Type

    Type:

    Self-Catering

    Niton Undercliff

    At St Catherine's Point, the southern most tip of the Island, the National Trust Knowles Farm self-catering holiday cottage is in a remote and wild spot close to the lighthouse and, you'll be please to know, the foghorn is no longer used.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  13. Add One Elm Cottage to your Itinerary

    One Elm Cottage

    Type

    Type:

    Self-Catering

    Roud, Godshill

    One Elm Cottage is a delightful stone cottage which sits on the edge of the ancient hamlet of Roud. It is one of a pair of cottages which can be booked together for gatherings of families and friends.

    Dates

    From:
    1 Jan 2026to31 Dec 2026

    Gradings

    • 4 Visit England Stars Self Catering
    4 Visit England Stars Self Catering
  14. Add Holiday Accommodation at Calbourne Water Mill to your Itinerary

    Holiday Accommodation at Calbourne Water Mill

    Type

    Type:

    Self-Catering

    CALBOURNE

    Amongst the 35 acre grounds of Calbourne Water Mill, one of the Island's main attractions, there are luxury eco lodges and traditional cottages.

    Dates

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

    Tourism For All

    Self-Assessed Accessibility Information

    Hill Croft Cottage

    Type

    Type:

    Self-Catering

    Niton Undercliff, Ventnor

    Hill Croft Cottage, located in an Area of Outstanding Natural Beauty in Niton Undercliff at the southern tip of the Island.

    Dates

    From:
    28 Feb 2026to12 Dec 2026
  16. Add Regent Street Townhouse to your Itinerary

    Regent Street Townhouse

    Type

    Type:

    Self-Catering

    Shanklin

    Set in the heart of Shanklin, Regent Street Townhouse is a beautifully designed retreat offering spacious accommodation, modern comforts, and easy access to one of the Isle of Wight’s most beloved seaside destinations. Whether you're looking for a…

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  17. Add Seafarers View to your Itinerary

    Seafarers View

    Type

    Type:

    Self-Catering

    Cowes

    Seafarer’s View is located a few steps away from the water’s edge on Cowes High Street on the beautiful and picturesque Isle of Wight. the property has been lovingly refurbished to operate as Serviced Accommodation, having 6 double bedrooms and 3…

    Dates

  18. Add Rookley Farm Lodge to your Itinerary

    Rookley Farm Lodge

    Type

    Type:

    Self-Catering

    ROOKLEY

    Rookley Farm Lodge is a spacious, comfortable, five bedroom house, with use of swimming pool and tennis court. Set in beautiful downland countryside in the centre of the Isle of Wight.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  19. Add Lyon Court - The Garden Apartment to your Itinerary

    Lyon Court - The Garden Apartment

    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
  20. Add National Trust The Old Club House Holiday Cottage to your Itinerary

    National Trust The Old Club House Holiday Cottage

    Type

    Type:

    Self-Catering

    ST HELENS

    A wooden chalet once the clubhouse for the Royal Isle of Wight Golf Links, now a National Trust self-catering holiday cottage in St Helens on the Isle of Wight.

    Dates

    From:
    1 Jan 2026to31 Dec 2026

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