Holiday cottages for 2021 in Isle of Wight

 Ready for a 2021 adventure? With the new year almost upon us, now's a great time to be thinking about your 2021 holiday.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 22 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 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £868

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


Upon opening the door of this most elegant and stylish home you will be in holiday heaven. The hallway leads you right through the house to an enclosed and well designed garden wit...

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

7 nights from £868

  • 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

  • Sleeps 6
  • Regret no pets
  • Changeover Sat

7 nights from £398

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


Right in the heart of the bustling sailing town of Cowes, 9 Crown Court offers great accommodation with a stunning roof terrace boasting uninterrupted views across the rooftops to ...

  • Sleeps 6
  • Regret no pets
  • Changeover Sat

7 nights from £398

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £308

1 bedroom self catering apartment with sea views in Seaview, Isle of Wight


This gorgeous top floor, one bedroom apartment has spectacular sea views over the rooftops across the Solent, and is just a few minutes from Seaview village and the beach. The Sai...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £308

We are Gold accredited with the Green Tourism Business Scheme.

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

7 nights from £863

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


With stunning sea views from not one but two balconies, 61 Solent View is a wonderful holiday destination within a few minutes' walk from Seagrove Bay. Located just on the outskirt...

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

7 nights from £863

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

7 nights from £746

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


A simply gorgeous three bedroom property just off St Helens' green on the eastern side of the Isle of Wight, The Haven is just a short walk from the coast and a ten minute stroll t...

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

7 nights from £746

Loading more