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 69 holiday cottages available in Isle of Wight for a two night break

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £295

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 £295

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

7 nights from £295

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 £295

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

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

7 nights from £435

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 £435

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

7 nights from £435

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 £435

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

7 nights from £380

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 £380

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £411

Orchard Cottage

3936

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


Originally the farm's milking parlour, this delightful semi-detached cottage sleeping four is the perfect cottage to spend quality time together as a family in a stunning rural loc...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £411

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £411

Dairy Cottage

3912

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


Originally the farm's milking parlour, Dairy Cottage is a light and airy single-storey cottage with plenty of charm throughout. Mattingly Farm is made up of three barns in total Da...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £411

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

7 nights from £434

Faithfull Cottage

3600

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...

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

7 nights from £434

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

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

7 nights from £441

Fir Cottage

3602

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


Located in a quiet lane a few steps from St Helens village green, Fir Cottage is a freshly decorated, refurbished Victorian semi-detached house, complete with all modern amenities....

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

7 nights from £441

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

7 nights from £449

Spindrift

4437

Tucked away but near the beach in Seaview, Isle of Wight.


This gorgeous two bedroom terraced cottage is a few minutes from the beach, right in the heart of Seaview village, offering an ideal holiday bolthole on the picturesque Isle of Wig...

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

7 nights from £449

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