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 27 self catering cottages available to rent in May in Sussex

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

7 nights from £1410

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 £1410

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

View
  • 10% off

    22 Aug 2025 - 29 Aug 2025

    From £627.00 £564.30

  • 10% off

    29 Aug 2025 - 5 Sep 2025

    £617.00 £555.30

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

Little Oak Farm

  • Sleeps 6 in 3 properties
  • Changeover Fri

7 nights from £272

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

Be in the know… Sign up to our newsletter for holiday inspiration, offers and all things Classic.

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

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 27 holiday cottages available this May in Sussex.