Holiday cottages for 2021 in Isle of Wight

 Ready to start planning your 2021 adventure? Now's a great time to get ahead of the crowd.Read more

Head to Cornwall, Devon, Somerset, Dorset, SussexIsle of Wight, Pembrokeshire or Kent with Classic in 2021. We have a portfolio of properties ready and waiting for you to start planning your next self catering holiday. Why not now and then relax later, knowing you've got your holiday for next year sorted. 

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

We have 79 Self catering holiday cottages for rent in 2021

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

7 nights from £563

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


A large and impressive building, Shanklin Manor is on the outskirts of Shanklin Old Village and within easy reach of all the amenities and the beach, making it a fabulous holiday d...

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

7 nights from £563

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £715

3 bedroom dog-friendly self catering cottage with sea views near Ventnor, Isle of Wight.


This gorgeous cottage, set in the breathtaking location of St Lawrence, has a large patio and unrivalled sea views. A truly magical place to sit and enjoy the scenery, the seaward ...

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £715

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

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

7 nights from £461

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


Upton View is a lovely cottage on the outskirts of Seaview with double doors opening out from the dining-area to a gorgeous garden and, with outdoor seating, you can while away you...

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

7 nights from £461

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £613

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


A stunning property in Ventnor on the southern tip of the Island, with the most sensational 180 degree sea views from the sun-drenched patio. Relax with your breakfast in the sunsh...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £613

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £815

3 bedroom self catering cottage near Ventnor, Isle of Wight


Set in the grounds of the impressive Pyle Manor, this newly refurbished cottage offers a wonderful base on the Isle of Wight with the shared use of an outdoor unheated swimming poo...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £815

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £429

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


Located in a quiet side street just off the village green in St Helens, this cosy cottage offers great accommodation with a good sized garden, spacious decking and outdoor seating ...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £429

  • Sleeps 10 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £1800

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


This is an absolutely stunning detached house situated along Ducie Avenue, a private unmade road leading to the beach, in the charming seaside village of Bembridge. Within a few mi...

  • Sleeps 10 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £1800

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £621

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, the h...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £621

Choose from our exclusive collection at the best prices with real time availability.

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £722

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
  • Regret no pets
  • Changeover Fri

7 nights from £722

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £893

5 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight


This is a three-storey house right in the heart of Bembridge village, just opposite the picturesque village church and a few minutes' walk from the shops and restaurants. The prope...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £893

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