Two night breaks in Isle of Wight

A weekend away or two night short break in Isle of Wight is so simple. No major preparations or need to pack up your life, just the perfect excuse to get away from it all for your favourite holiday cottage and slip under the radar of everyday life. With hand picked cottages across the south and west of the country there are endless places to escape to for a two night break with Classic Cottages. Take a look and see...

We have 97 holiday cottages available in Isle of Wight for a two night break

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

7 nights from £280

The Battenburg Studio

3664

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


This contemporary studio apartment enjoys a great location in Shanklin. With modern decor and open plan living, it makes a cosy retreat for a couple looking for a coastal break. ...

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

7 nights from £280

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £280

The Beatrice Studio

3666

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


Located on the first floor of Shanklin Villa, a lovely Victorian property, this small studio apartment packs a punch despite its size. Enjoying beautiful sea views from its elevate...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £280

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

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

7 nights from £292

Mariners Cove

3628

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 th...

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

7 nights from £292

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

7 nights from £293

Berryl Mead View

3906

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. It is well-equipped throughout and has an extremely comfortable li...

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

7 nights from £293

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

7 nights from £356

Grace Cottage

4209

1 bedroom, dog friendly holiday cottage near 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
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £356

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

7 nights from £415

The Cadogan Apartment

3667

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


Sitting within a beautifully converted Victorian villa, The Cadogan Apartment offers a high standard of accommodation for a couple or lone traveller looking for a coastal break. Gu...

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

7 nights from £415

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £415

The Worsley Apartment

3682

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


Offering a high standard of accommodation, The Worsley Apartment is a ground floor apartment within Shanklin Villa, a beautifully converted Victorian building. With a separate kitc...

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £415

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

7 nights from £335

Hove To

3767

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


Hove To is one of a collection of bungalows located along the Seaview Duver. Situated on the corner, it benefits from a large decked-area on two sides with a lovely outlook over th...

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

7 nights from £335

We’ve been raising the standards of self catering holidays since 1977.

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

7 nights from £335

Cockleshells

3815

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 accommodation offers a double...

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

7 nights from £335

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

7 nights from £369

2 Bermuda

3517

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


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 £369

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