Cottages for October Half Term on the Isle of Wight

101 luxury cottages for October half term on the Isle of Wight

House of Logs is a 4 bedroom, rural self catering cottage near the beach in Totland, Isle of Wight
  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £941 booking fees included

House of Logs

4225

4 bedroom, rural self catering cottage near the beach in Totland, Isle of Wight


House of Logs is a unique and stunning property located on the west coast of the Island, just a short walk from Widdick Chine and Totland Bay. Perfect for a peaceful holiday and do...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £941

Oak Tree Cottage is a 3 bedroom self catering cottage with sea views in Seaview, Isle of Wight
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1063 booking fees included

Oak Tree Cottage

4212

3 bedroom self catering cottage with sea views in Seaview, Isle of Wight


With gorgeous views over the Solent and the beach just a few steps away, Oak Tree Cottage is a delightful reverse level holiday home situated a short stroll from the village centre...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1063

Grace Cottage is a 1 bedroom holiday cottage close to the sea near Ventnor, Isle of Wight
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £659 booking fees included

Grace Cottage

4209

1 bedroom holiday cottage close to the sea near Ventnor, Isle of Wight


This gorgeous barn conversion is set within the grounds of the stunning North Grounds Farm, just outside the village of Chale Green on the southern side of the Island. For the envi...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £659

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  • 20% off

    24 Jul 2026 - 31 Jul 2026

    £913.00 £743.00 booking fees included

Bayside House is a 4 bedroom, rural self catering cottage near the beach in Yarmouth, Isle of Wight
  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £1821 booking fees included

Bayside House

4178

4 bedroom, rural self catering cottage near the beach in Yarmouth, Isle of Wight


This beautiful house is set in several acres of garden on the outskirts of Yarmouth, just a few minutes' walk to the water’s edge, a truly stunning holiday destination. The pro...

  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £1821

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

Keepers Cottage is a 4 bedroom, rural self-catering cottage on the outskirts of Wootton, Isle of Wight
  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £979 booking fees included

Keepers Cottage

4070

4 bedroom, rural self-catering cottage on the outskirts of Wootton, Isle of Wight


This gorgeous stone cottage is tucked away in the most idyllic and tranquil location; surrounded by fields and woodland, this is the perfect holiday setting to truly escape from it...

  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £979

The New House is a 4 bedroom self catering cottage in Godshill, Isle of Wight
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1257 booking fees included

The New House

4025

4 bedroom self catering cottage in Godshill, Isle of Wight


Nestled in the heart of the chocolate-box village of Godshill, this detached house has beautiful secluded gardens to the rear and everything the village can offer within a few minu...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1257

St Albans House is a 4 bedroom self catering cottage with sea views near Ventnor, Isle of Wight
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1006 * booking fees included

St Albans House

3980

4 bedroom self catering cottage with sea views near Ventnor, Isle of Wight


This large detached house is situated in an elevated position as you enter the town of Ventnor, with the most breathtaking views from virtually every room. The beautiful tiered...

  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1006 *

Flackstead is a 3 bedroom self catering cottage near the beach in Brook, Isle of Wight
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2170 booking fees included

Flackstead

3913

3 bedroom self catering cottage near the beach in Brook, Isle of Wight


Flackstead is a stunning eco-friendly house which has breathtaking and uninterrupted coastal views across Compton Bay towards The Needles. Perfect for both families and small group...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2170

Bay View is a 2 bedroom, rural holiday apartment near the beach in Freshwater, Isle of Wight
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £986 * booking fees included

Bay View

3902

2 bedroom, rural holiday apartment near the beach in Freshwater, Isle of Wight


Perched above the stunning Freshwater Bay, this elegant contemporary apartment offers breathtaking views of the scenic coastline and the ultimate spot for refreshing seaside dips. ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £986 *

6 St Josephs is a 2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £608 booking fees included

6 St Josephs

3846

2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight


6 St Josephs is a top floor apartment with stunning panoramic sea views, which you can admire from the balcony, sitting-room and main bedroom! Ideally positioned between Bonchurch ...

  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £608

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