Cottages For May in Sussex

Cottages For May in Sussex

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 Sussex Read more

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

We have 30 self catering cottages available to rent in May in Sussex

The Old Tractor Shed is a 2 bedroom, dog friendly self catering cottage near Winchelsea.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £741 booking fees included

The Old Tractor Shed

6180

2 bedroom, dog friendly self catering cottage near Winchelsea.


Tucked away on a working sheep farm close to the coast and the medieval towns of Rye and Winchelsea, this peaceful escape is surrounded by beautiful farmland and scenic footpaths i...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £741

Bloomsbury Cottage is a 1 bedroom, dog friendly self catering cottage in Wadhurst.
  • Sleeps 2 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £601 booking fees included

Bloomsbury Cottage

6186

1 bedroom, dog friendly self catering cottage in Wadhurst.


For a digital detox head to the beautiful countryside of the High Weald National Landscape to stay at this unique timber-cladded barn that offers a peaceful escape just moments fro...

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

7 nights from £601

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Broyle Cottage is a 3 bedroom, dog friendly self catering cottage near Hailsham.
  • Sleeps 6
  • Dogs welcome
  • Changeover Fri

7 nights from £816 * booking fees included

Broyle Cottage

6174

3 bedroom, dog friendly self catering cottage near Hailsham.


Tucked away in a peaceful hamlet near the village of Herstmonceux, this quintessential English country cottage lends itself to family gatherings, celebrations or romantic breaks. B...

  • Sleeps 6
  • Dogs welcome
  • Changeover Fri

7 nights from £816 *

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

From £84 per night + £63 booking fees

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

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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 £721 booking fees included

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 £721

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 £959 booking fees included

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 £959

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 £741 booking fees included

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 £741

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

7 nights from £1063 booking fees included

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 £1063

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

7 nights from £514 booking fees included

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 £514

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

From £66 per night + £53 booking fees

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 £66 per night

Choose from our exclusive collection at the best prices with real time availability.

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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 Sussex. So have a look through our 30 holiday cottages available this May in Sussex.