Holiday Cottages for October on the Isle of Wight

Holiday Cottages for October on the Isle of Wight

Although you may not expect it to be so, the Isle of Wight often benefits from lots of sunshine and mild weather well into October. With the sea warmed from months of the sun's rays and the atmosphere calm, it is a truly wonderful time of year to explore the island. Book a luxury retreat and enjoy the island from a home-from-home this October.Read more

Rolling countryside bearing colours of rust, deep red and burnt orange, long sandy beaches bathed in warm sunshine and quiet towns and promenades: this is October on the Isle of Wight. However you'd like to spend your holiday and whoever you'd like to share it with, the Isle of Wight offers a beautiful playground where adventure beckons. With as many opportunities to relax as to explore, you can spend your days exactly as you please and return to your own slice of paradise. At Classic Cottages, we pride ourselves on marketing only the highest quality self-catering accommodation around.  Handpicking and personally inspecting each property, we make sure each meets exacting standards so your whole holiday is the best it can be. Browse our 125 available cottages to find your perfect one, or get in touch for more information. 

125 self-catering cottages on the Isle of Wight

Driftwood is a 2 bedroom, dog friendly holiday cottage near the beach in Freshwater, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1056

Driftwood

5613

2 bedroom, dog friendly holiday cottage near the beach in Freshwater, Isle of Wight.


Whisk yourself away to this pretty retreat on the glorious Isle of Wight, perfect for couples and families and your four-legged companions who love to explore as much as you do, an...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1056

View
  • 20% off

    12 Apr 2024 - 19 Apr 2024

    £1064.00£851.20

Escape Away is a 2 bedroom self catering cottage near the beach in Freshwater.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £1056

Escape Away

5612

2 bedroom self catering cottage near the beach in Freshwater.


Close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base yourself for a peaceful and relaxing h...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £1056

View
  • 20% off

    12 Apr 2024 - 19 Apr 2024

    £1064.00£851.20

Blakesley Cottage is a 2 bedroom, dog friendly self catering cottage in Godshill, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £644

Blakesley Cottage

5565

2 bedroom, dog friendly self catering cottage in Godshill, Isle of Wight.


Nestled in the very heart of the Isle of Wight's rolling countryside close to the quintessential English village of Godshill yet just a short drive away from the stunning beaches o...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £644

Bagwich House

  • Sleeps 12 + 3 cots in 3 properties
  • Changeover Sat

7 nights from £1829

Tamarisk House 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 £2517

Tamarisk House

5516

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


If you are seeking the ultimate coastal getaway with more than a little exclusivity, look no further than this luxurious retreat in Seaview overlooking the beautiful Solent on the ...

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

7 nights from £2517

Halland Rise is a 4 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1720 *

Halland Rise

5500

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


Introducing, Halland Rise, a stunning detached house sleeping eight guests, nestled in Seaview, one of the Island's most sought-after villages. With a choice of hidden coves and lo...

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

7 nights from £1720 *

Firestone Lodge is a 4 bedroom, dog friendly holiday cottage near the beach near Ryde, Isle of Wight.
  • Sleeps 7 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1683

Firestone Lodge

5494

4 bedroom, dog friendly holiday cottage near the beach near Ryde, Isle of Wight.


Set back from the road and only a short walk from the pretty tidal estuary at Wootton Creek, Firestone Lodge sets the scene for your luxury holiday with family, friends and your mu...

  • Sleeps 7 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1683

Dar View is a 4 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1748

Dar View

5458

4 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.


If you are looking for a stylish, spacious, yet comfortable retreat which boasts a superbly sought-after location, welcome to Dar View. An exquisite 'New England' style holiday...

  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1748

Lower Buoys is a 2 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
  • Sleeps 4
  • No pets
  • Changeover Sat

7 nights from £960

Lower Buoys

5457

2 bedroom self catering apartment near the beach in Seaview, Isle of Wight.


Looking for buried treasure and an Island adventure? Look no further than this super ground floor, luxuxy apartment in a premier destination in the heart of Seaview. Enjoy beachsid...

  • Sleeps 4
  • No pets
  • Changeover Sat

7 nights from £960

Lazydays Hideaway is a 1 bedroom glamping Yurt with sea views near Ventnor, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

From £180 per night

Lazydays Hideaway

5381

1 bedroom glamping Yurt with sea views near Ventnor, Isle of Wight.


Welcome to Lazydays Hideaway, enjoying far reaching sea views across Reeth Bay and beyond and nestled on a hillside at the southerly point of the Isle of Wight. Whether you wan...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

From £180 per night

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