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…

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…

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…

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Search Self-Catering

Type:
Where:
Keyword:
Arrival Date:
Add Room / Unit

Isle of Wight self catering

Number of results:

Number of results: 275

, currently showing 241 to 260.

  1. Add Snaptrip to your Itinerary

    Snaptrip

    Type

    Type:

    Self-Catering

    ISLANDWIDE

    Home to the largest collection of self-catering accommodation on the Isle of Wight, Snaptrip is a trusted marketplace for holiday cottages online.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  2. 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
  3. Add Swysh Stays to your Itinerary

    Swysh Stays

    Type

    Type:

    Self-Catering

    Whitwell, VENTNOR

    We’re Swysh Stays - a luxury Isle of Wight holiday home company with a curated collection of top-notch properties, from characterful cottages to seaside apartments and snug, homely boltholes, we’re sure to have something for everyone.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  4. 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
  5. 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
  6. Add Big Domain to your Itinerary

    Big Domain

    Type

    Type:

    Self-Catering

    ISLANDWIDE

    Packed full of family-friendly attractions, and boasting one of the finest coastlines in all of the UK, the Isle of Wight is perfect for a holiday with all the family or a group of friends. Visit some of the popular coastal resorts such as Sandown,…

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  7. 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
  8. Add SeaviewsinRyde to your Itinerary

    SeaviewsinRyde

    Type

    Type:

    Self-Catering

    RYDE

    Large pet-friendly house on three floors with a semi-contained ground floor annex.  Ideal for multigenerational or multiple families or just for escaping the teenagers. 

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  9. Add Fernhill Barns to your Itinerary

    Fernhill Barns

    Type

    Type:

    Self-Catering

    RYDE

    A collection of 4 spacious and contemporary barn conversions sleeping up to 18.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  10. Add Ocean Deck Apartment to your Itinerary

    Ocean Deck Apartment

    Type

    Type:

    Self-Catering

    SHANKLIN

    Stunning ground floor apartment with beautiful views overlooking the country garden and coastline. Sleeps four to six with two bedrooms and two bathrooms. Children and babies welcome.

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  11. 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
  12. Add Longwood Edge to your Itinerary

    Tourism For All

    Self-Assessed Accessibility Information

    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
  13. Add St Catherine's Cottage to your Itinerary

    St Catherine's Cottage

    Type

    Type:

    Self-Catering

    Freshwater

    St Catherine's Cottage is a bright and cosy three-bedroom Victorian cottage offering enclosed gardens and a balcony with sea views. Situated on a peaceful lane beside Tennyson Down, St Cats is 450m from the charming beach at Freshwater Bay. 

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  14. Add Wightsands Holiday Let to your Itinerary

    Wightsands Holiday Let

    Type

    Type:

    Self-Catering

    RYDE

    2 quality, detached holiday lets just a 4 minutes stroll from a soft, sandy beach at Appley. Childrens toy filled playden in private garden, off road parking and free wifi.

    Dates

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

    Hilda Cottage

    Type

    Type:

    Self-Catering

    BEMBRIDGE

    Enjoy a beach-side holiday at Hilda Cottage (sleeps 6 + dog).  Just 1 minute walk to the beach, this fantastic house and sunny garden is very well-appointed and has been furnished to a high specification.

    Dates

    From:
    1 Jan 2026to31 Dec 2026

    Gradings

    • Visitor Ready Accredited by VisitEngland
    Visitor Ready Accredited by VisitEngland
  16. Add Calico Skies to your Itinerary

    Calico Skies

    Type

    Type:

    Self-Catering

    NEWPORT

    Nestled in the tranquil setting of Island Harbour Marina, Calico Skies is a beautifully designed retreat offering waterfront views, modern comforts, and direct access to one of the Isle of Wight’s most sought-after boating locations. Whether you're…

    Dates

    From:
    1 Jan 2026to31 Dec 2026
  17. Add Clevelands Country House & Apartments to your Itinerary

    Clevelands Country House & Apartments

    Type

    Type:

    Self-Catering

    WROXALL

    Clevelands holiday properties are situated in semi rural village on the south side of the island and close to beaches of Ventnor& Shanklin.

    Country House is perfect for celebrations, reunions, groups of friends and families to celebrate occasions…

    Dates

    From:
    1 Jan 2023to31 Jan 2026
  18. 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
  19. Add Cosy Cottage to your Itinerary

    Cosy Cottage

    Type

    Type:

    Self-Catering

    FRESHWATER

    Situated in Freshwater on the Isle of Wight, set in two acres of beautiful gardens sat back from the road, Cosy Cottage is a hidden gem of tranquillity on the West Wight.

    Dates

  20. 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

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