Holiday cottages for October in South England

Holiday cottages for October in South England

Savour the crunch of leaves underfoot, the quiet beaches and the autumnal woodland with a holiday cottage in the UK for October half term.Read more

We’re not promising, but you could be on the beach enjoying the best the South and West has to offer. And at this time of year you can also bring the dog, or grab your surfboard as the Atlantic swells start rolling in and the sea is still warm, well fairly! If stormy seas don’t float your boat, it is a great time to explore the many gardens and woodlands in the area as they put on golden autumnal coats for their end of year display. Bring the family during October half-term to relive memories of a spent summer or indulge in a luxury short break before the winter kicks in.

Our exclusive ferry discounts will make your island trip with Classic plain sailing.

We've got 147 holiday cottages matching your search in the South of England...

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 £1110

Oak Tree Cottage

4212

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


With a stunning spacious sea facing balcony, Oak Tree Cottage is in a superb location just steps from the beach and a short walk along the seafront into Seaview Village. An outdoor...

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

7 nights from £1110

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 £652

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 £652

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

7 nights from £765

1 St Josephs

4183

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


With one of the best views on the Isle of Wight, 1 St Josephs is a superb ground floor apartment beautifully decorated throughout. The property has a large patio area spanning two ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £765

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 £2045

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 £2045

Our guests rate us 4.8/5 on Feefo, the independent review site.

61 Solent View is a 4 bedroom, dog friendly holiday cottage, with sea views in Seaview, Isle of Wight
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1012 *

61 Solent View

4078

4 bedroom, dog friendly holiday cottage, with sea views in Seaview, Isle of Wight


On the outskirts of Seaview and within a few minutes' walk from Seagrove Bay, take in the stunning sea views from not one but two balconies. 61 Solent View is a wonderful holiday h...

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

7 nights from £1012 *

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 £926

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 £926

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 £1298

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 £1298

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 £1036

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 £1036

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 £975

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 £975

Solent Heights is a 5 bedroom self catering cottage near the beach in Cowes, Isle of Wight
  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £2336

Solent Heights

3946

5 bedroom self catering cottage near the beach in Cowes, Isle of Wight


A beautifully designed, contemporary home in the popular sailing town of Cowes, Solent Heights boasts sea views and quality finishes throughout. Set over four floors - including ba...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £2336

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

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