Holiday Cottages for 2020 on the Isle of Wight

Holiday on the Isle of Wight and let 2020 be a year to remember. All of our holiday cottages are personally inspected and fully equipped, ensuring your holiday is the best it can be. Book now to secure your favourite cottage. Read more

 Now's a great time to be booking for next year. Our portfolio gets better year after year, with all the old favourites and some stunning new additions, so get in there quick and book your 2020 holiday cottage before someone else does. Browse our list of 68 available cottages..

 

Pay only £30 today and the remainder of your deposit is not due until 5th September, giving you all summer to sit back and relax, knowing that extra special place is all yours for 2020*. From Cornwall to Dorset, Devon to Somerset and even as far as the Isle of Wight, take a look at our collection now and start dreaming of your next holiday with Classic Cottages.

 

Pick a place close to the coast for that year-round holiday vibe, or book a holiday townhouse to be close to every convenience. Escape to the country for peace and quiet or take to the moors for walks through wide open spaces, we’ve got 68 holiday cottages for 2020 you to choose from...

 

*Click here for terms and conditions.

 

 

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

68 self-catering cottages on the Isle of Wight

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £287

1 bedroom self catering apartment near the beach in Bembridge, Isle of Wight.


This charming one bedroom apartment forms part of a country house, set around a shared Spanish-style courtyard, just outside the bustling village of Bembridge. You can enjoy the ev...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £287

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £288

1 bedroom self catering cottage near Ventnor, Isle of Wight


Located in a rural village setting, Berryl Mead View is a delightful home from home cottage with plenty of space, well equipped throughout and extremely comfortable living room wit...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £288

Need more time? Reserve any cottage for up to 24 hours before booking.

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £320

1 bedroom, rural self catering cottage in Newport, Isle of Wight


This absolutely gorgeous barn conversion is the perfect place for a couple's holiday, located on the Durton Farm Estate in the centre of the Island. Lovingly refurbished by the own...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £320

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £328

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


Cockleshells is one of the charming Salterns bungalows situated along the Seaview Duver within a short walk to the Yacht Club and Seaview Village. The new Owner has completely rede...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £328

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £334

2 bedroom, dog-friendly holiday cottage with sea views in East Cowes, Isle of Wight


Smugglers' Run is a waterside property overlooking the River Medina and across to the sailing town of Cowes. It would suit a family or a couple in need of a little extra space. ...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £334

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £343

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


Faithfull Cottage is a lovingly restored, pretty mid-terrace cottage which enjoys a rear garden and countryside views on the outskirts of St Helens. This comfortable cottage is set...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £343

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £360

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
  • Regret no pets
  • Changeover Sat

7 nights from £360

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £360

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


6 St Joseph’s has stunning panoramic sea views, which you can sit and admire from the balcony, living room and master bedroom! Ideally positioned between Bonchurch and Ventnor this...

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £360

Our property managers are local experts who handpick perfect places to stay.

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £362

2 bedroom self catering apartment with sea views in Seaview.


2 Bermuda is a lovely, neutrally decorated first floor apartment with wonderful views across the Solent, a balcony for al fresco drinks and a pretty garden. With both the beach and...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £362

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £373

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


5 Sandpipers is a well-equipped, modern house set within a small development in the heart of Seaview. It offers comfortable accommodation for a couple or small family. The sitt...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £373

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