Two night breaks in Isle of Wight

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 UK, there are endless places to escape to for a two night break with Classic Cottages. Take a look and see...

We have 47 holiday cottages available in Isle of Wight for a two night break

Bagwich House

  • Sleeps 12 + 3 cots in 3 properties
  • Changeover Sat

7 nights from £1793

Blakesley Cottage is a 2 bedroom, dog friendly self catering cottage in Godshill, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £714

Blakesley Cottage

5565

2 bedroom, dog friendly self catering cottage in Godshill, Isle of Wight.


Nestled in the very heart of the Isle of Wight's rolling countryside close to the quintessential English village of Godshill yet just a short drive away from the stunning beaches o...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £714

Lazydays Hideaway is a 1 bedroom glamping Yurt with sea views near Ventnor, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

From £180 per night

Lazydays Hideaway

5381

1 bedroom glamping Yurt with sea views near Ventnor, Isle of Wight.


Welcome to Lazydays Hideaway, enjoying far reaching sea views across Reeth Bay and beyond and nestled on a hillside at the southerly point of the Isle of Wight. Whether you wan...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

From £180 per night

Forget Me Not Cottage is a 3 bedroom self catering cottage near the beach in Bembridge, Isle of Wight
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £991

Forget Me Not Cottage

5167

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


Welcome to the delightfully named Forget Me Not Cottage, a charming three bedroom getaway in the pretty coastal town of Bembridge. With its homely interiors and great location, thi...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £991

10 Bayclose is a 2 bedroom self catering apartment with sea views in Freshwater, Isle of Wight
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £547

10 Bayclose

5159

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


Overlooking the gorgeous coastline at Freshwater Bay sits 10 Bayclose, a wonderfully homely apartment perfect for a family getaway to the seaside. With light and airy interiors, sn...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £547

Stargazers' Retreat is a Luxury Yurt for 5 near the beach near Ventnor, Isle of Wight.
  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £1020 *

Stargazers' Retreat

5125

Luxury Yurt for 5 near the beach near Ventnor, Isle of Wight.


Welcome to Stargazers' Retreat, a heavenly glamping yurt nestled in rural splendour on the southerly tip of the Isle of Wight with blissful views of Reeth Bay and beyond. Situated ...

  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £1020 *

View
  • 15% off

    23 Feb 2024 - 1 Mar 2024

    £1200.00£1020.00

  • 15% off

    1 Mar 2024 - 8 Mar 2024

    £1080.00£918.00

  • 15% off

    8 Mar 2024 - 15 Mar 2024

    £1080.00£918.00

Sea Lights is a 2 bedroom self catering apartment with sea views in Cowes, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £987

Sea Lights

4967

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


Situated close to the beating heart of world-famous Cowes, lies the pretty coastal village of Gurnard, where you will find this handsome coastal ground floor pet friendly apartment...

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

7 nights from £987

Old Bembridge House is a 3 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 6
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £835

Old Bembridge House

4791

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


Tucked away on an unmade track just a few yards from the sea and Bembridge Yacht club, Old Bembridge House has all the makings of a perfect holiday idyll. Laid across three floors,...

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

7 nights from £835

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

1 Harrow Cottages is a 1 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £358

1 Harrow Cottages

4642

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


This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from...

  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £358

Limpets  is a 3 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
  • Sleeps 5 + cot
  • No pets
  • Changeover Sat

7 nights from £861

Limpets

4622

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


This gorgeous home, just a stone's throw from the seafront, has sea views from the sitting-room and the luxury of your very own private garden, giving it all the ingredients for a ...

  • Sleeps 5 + cot
  • No pets
  • Changeover Sat

7 nights from £861

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