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 24 self catering cottages available to rent in May in Sussex

Little Oak Farm

  • Sleeps 6 in 3 properties
  • Changeover Fri

7 nights from £272

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

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

Mellifount Farm is a 2 bedroom self catering cottage near Haywards Heath.
  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £717

Mellifount Farm

5839

2 bedroom self catering cottage near Haywards Heath.


Escape to the Sussex countryside and stay in this beautiful oak-framed barn situated in a quiet rural location overlooking wooded farmland and paddocks, where you can sometimes see...

  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £717

Strawberry Hole Barn is a 2 bedroom thatched, dog friendly self catering cottage near Rye.
  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £802

Strawberry Hole Barn

5814

2 bedroom thatched, dog friendly self catering cottage near Rye.


Escape to this gorgeous thatched barn, sat in the grounds of the owners' double oast house, within walking distance of Great Dixter House and Gardens. This spacious property offers...

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

7 nights from £802

Pump Cottage is a 2 bedroom self-catering cottage in Rye.
  • Sleeps 3 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £497

Pump Cottage

5788

2 bedroom self-catering cottage in Rye.


Situated in the heart of Rye and just a short walk from the railway station, Pump Cottage is perfectly positioned for exploring this medieval town, 1066 country and the golden beac...

  • Sleeps 3 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £497

The Laundry is a 2 bedroom, dog friendly self catering cottage near Polegate.
  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £787

The Laundry

5650

2 bedroom, dog friendly self catering cottage near Polegate.


This retro-style retreat is the perfect place to relax, recharge and reconnect. It sits in the picturesque downland village of Jevington within the South Downs National Park, just ...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £787

Hayesland Lodge is a 1 bedroom, dog friendly self catering cottage near Rye.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £597

Hayesland Lodge

5700

1 bedroom, dog friendly self catering cottage near Rye.


This gem is situated in a peaceful and tranquil setting in a National Landscape (an Area of Outstanding Natural Beauty) with farmland views, a short drive from the coast and the me...

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £597

Beacon Hill Barn is a 2 bedroom self catering cottage near Midhurst.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £904

Beacon Hill Barn

5644

2 bedroom self catering cottage near Midhurst.


This gorgeous barn sits in the heart of the South Downs National Park providing an excellent base for all types of rural pursuits and is perfectly positioned for visiting the towns...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £904

Our guests rate us 4.8/5 on Feefo, the independent review site.

Darjeeling Lodge is a 2 bedroom, dog friendly self catering cottage near Rye.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £646

Darjeeling Lodge

5598

2 bedroom, dog friendly self catering cottage near Rye.


If you're looking for a peaceful or romantic break in the heart of the Sussex countryside, then this is the place for you! Situated in Beckley, near the village of Broak Oak, Darje...

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

7 nights from £646

4 Church Square is a 1 bedroom, dog friendly self catering cottage in Rye.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £662

4 Church Square

5520

1 bedroom, dog friendly self catering cottage in Rye.


Welcome to this gorgeous Grade II Listed cottage situated along one of Rye's famous cobbled streets, perfect for couples looking to stay in the heart of Rye. As you enter this ...

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

7 nights from £662

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 Sussex. So have a look through our 24 holiday cottages available this May in Sussex.