Cottages For May in South England

Cottages For May in South England

Shhh! Don’t tell too many people this but, if you’re looking for a cottage holiday in May you might have stumbled on one of the best months to visit South England Read more

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

We have 125 self catering cottages available to rent in May in South England

Rockfield Lodge is a 3 bedroom, dog friendly self catering cottage near Battle.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £935

Rockfield Lodge

6054

3 bedroom, dog friendly self catering cottage near Battle.


Situated in beautiful grounds just outside the medieval town of Battle and a short drive from Hastings and St Leonards-on-Sea, this delightful lodge offers a spacious holiday abode...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £935

The Police House is a 4 bedroom, dog friendly holiday cottage near the beach in Seaview.
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1113 *

The Police House

6051

4 bedroom, dog friendly holiday cottage near the beach in Seaview.


Perfectly situated in the heart of the charming village of Seaview on the stunning east coast of the Isle of Wight, The Police House is a delightful, detached holiday home located ...

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

7 nights from £1113 *

Ellenhall is a 4 bedroom, dog friendly self catering cottage near Battle.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1572

Ellenhall

5990

4 bedroom, dog friendly self catering cottage near Battle.


Escape to this picture-perfect countryside retreat which sits in a salubrious location in the High Weald National Landscape (Area of Outstanding Natural Beauty). Surrounded by anci...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1572

Carter's Cottage is a 1 bedroom self catering cottage near Hailsham.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £450

Carter's Cottage

6005

1 bedroom self catering cottage near Hailsham.


This cosy and well-appointed semi-detached country retreat sits on a working heavy horse farm, perfect for couples or solo travellers looking to unwind, reconnect and enjoy the slo...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £450

Seascape is a 2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.
  • Sleeps 3
  • No pets
  • Changeover Sat

7 nights from £591

Seascape

5944

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


Located in the cosmopolitan town of Ventnor within a Victorian townhouse, Seascape is a modern two-bedroom, ground floor, apartment with spectacular sea views overlooking the bay. ...

  • Sleeps 3
  • No pets
  • Changeover Sat

7 nights from £591

Maybury is a 3 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1240

Maybury

5991

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


Your dream coastal escape awaits in Seaview! Escape to elegant Maybury and stay in this beautifully styled home with sandy beaches and village amenities on your doorstep. This blis...

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

7 nights from £1240

Fenders is a 3 bedroom, dog friendly cottage near the beach in Totland.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1041

Fenders

5987

3 bedroom, dog friendly cottage near the beach in Totland.


Your memorable Isle of Wight coastal escape awaits at Fenders, a beautifully appointed single-storey retreat, situated just moments from the picturesque beach at Totland Bay. Tucke...

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

7 nights from £1041

Little Oak Farm

  • Sleeps 6 in 3 properties
  • Changeover Fri

7 nights from £272

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

Isla Rose is a Dog friendly shepherds hut near Pulborough.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

From £91 per night

Isla Rose

5948

Dog friendly shepherds hut near Pulborough.


This oh-so-romantic shepherd's hut for two lies in the beautiful countryside of West Sussex and offers an idyllic, peaceful escape that's dog friendly too. Just a mere two hours...

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

From £91 per night

Sun Lodge is a 4 bedroom, dog friendly holiday cottage with sea views in Ventnor.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1369

Sun Lodge

5853

4 bedroom, dog friendly holiday cottage with sea views in Ventnor.


Step back in time and immerse yourself in the historic charm of Ventnor at this elegant Isle of Wight retreat with mesmerising sea views and generous spaces for a truly relaxing fa...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1369

Load more

Spring is in full swing, it is often one of our sunniest months and some of the best local festivals start. And you get the pick of the properties in South England. So have a look through our 125 holiday cottages available this May in South England.