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

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

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

48 Solent View is a 3 bedroom self catering cottage with sea views in Seaview.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £986

48 Solent View

5828

3 bedroom self catering cottage with sea views in Seaview.


Just a short wander from the golden sands of Seagrove Bay and the quaint charm of Seaview village, this stylish holiday haven offers modern home comforts in an unbeatable location ...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £986

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

Pucks Oak is a 4 bedroom, dog friendly holiday cottage with sea views in Seaview.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1135

Pucks Oak

5698

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


Within moments of the seafront at Seaview, with off-street parking and a lovely garden, semi-detached Pucks Oak is a great home-from-home to enjoy with friends and family. With the...

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

7 nights from £1135

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

We are Gold accredited with the Green Tourism Business Scheme.

Pepita is a 5 bedroom, dog friendly holiday cottage with sea views in Seaview.
  • Sleeps 9 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1888 *

Pepita

5719

5 bedroom, dog friendly holiday cottage with sea views in Seaview.


With breathtaking sea views and the beach only a few steps from the front door, two former coastguard cottages and the adjoining boathouse have been transformed into an island gem,...

  • Sleeps 9 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1888 *

The Dairy is a 3 bedroom self catering cottage near the beach in Seaview.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1249

The Dairy

5631

3 bedroom self catering cottage near the beach in Seaview.


Set in the pretty village of Seaview, moments from the seafront, this delightful home-from-home is waiting to welcome you. The village centre is a short stroll away, here you will ...

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

7 nights from £1249

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 79 holiday cottages available this May in South England.