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 101 self catering cottages available to rent in May in South England

Bramley Lodge is a 1 bedroom self catering cottage near Heathfield.
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

From £84 per night

Bramley Lodge

6137

1 bedroom self catering cottage near Heathfield.


Soak up the scenic views of this enchanting lodge that sits within an orchard in the High Weald National Landscape. Its peaceful location is the perfect escape for a romantic getaw...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

From £84 per night

Bay Cottage is a 2 bedroom self catering cottage near the beach in Cowes.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £697

Bay Cottage

6150

2 bedroom self catering cottage near the beach in Cowes.


Tucked away in the charming village of Gurnard on the northwest coast of the Isle of Wight, this cosy two bedroom cottage offers a relaxed coastal lifestyle, complete with a pretty...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £697

Little Field is a 3 bedroom, dog friendly holiday cottage near the beach near Ryde.
  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £896 *

Little Field

6123

3 bedroom, dog friendly holiday cottage near the beach near Ryde.


Tucked away on a quiet road, Little Field has been lovingly built by the owners and offers guests a peaceful and tranquil retreat with oodles of space and modern living. Situated o...

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

7 nights from £896 *

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

7 nights from £1131

Dunks Cottage

6074

4 bedroom, dog friendly self catering cottage near Cranbrook.


Overlooking the village green of Sandhurst, Kent, in the beautiful High Weald National Landscape (Area of Outstanding Natural Beauty), this wonderfully spacious, semi-detached cott...

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

7 nights from £1131

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Best company for UK holiday home rentals

Nobby Nook is a 1 bedroom, dog friendly self catering cottage near Battle.
  • Sleeps 2 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Thu

7 nights from £657

Nobby Nook

6006

1 bedroom, dog friendly self catering cottage near Battle.


This characterful gem, nestled in beautiful Sussex countryside, offers the perfect retreat for couples and solo travellers seeking a luxury escape. Nobby Nook is a lovingly conv...

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

7 nights from £657

Austin House is a 3 bedroom self catering cottage near the beach in Worthing.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £787 *

Austin House

6019

3 bedroom self catering cottage near the beach in Worthing.


Situated in the heart of Worthing, just a short walk from the seafront with its long promenade and Victorian pier, this spacious house is perfect for family get-togethers and those...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £787 *

Pomona Annexe is a 2 bedroom, dog friendly self catering cottage in Battle.
  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £677

Pomona Annexe

6053

2 bedroom, dog friendly self catering cottage in Battle.


Located just a short drive from the stunning Sussex coast and a short ten-minute walk to the RSPB Fore Wood Nature Reserve and the iconic town of Battle, Pomona Annexe is a charmin...

  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £677

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 £518

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 £518

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

7 nights from £504

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

7 nights from £504

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

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 101 holiday cottages available this May in South England.