Cottages for May bank holidays in South England

Cottages for May bank holidays in South England

May is when South England comes alive, the winter is left behind and a sunny day feels like summer in a early May bank holiday cottage. Read more

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

We have 107 available for the May Day bank holiday in South England

1 Harrow Cottages is a 1 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £362

1 Harrow Cottages

4642

1 bedroom self catering apartment near the beach in Seaview, Isle of Wight.


This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from...

  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £362

The Tea Hut is a 1 bedroom, dog-friendly self-catering cottage near Crowborough and the Ashdown Forest.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £369

The Tea Hut

4477

1 bedroom, dog-friendly self-catering cottage near Crowborough and the Ashdown Forest.


The Tea Hut is situated up a private drive in High Hurstwood. Nestled in the picturesque Sussex countryside it is a great base from which to explore Ashdown Forest and the local to...

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

7 nights from £369

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

7 nights from £378

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 £378

Sawmill Cottage is a 1 bedroom, dog-friendly self-catering cottage in Royal Tunbridge Wells.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £462

Sawmill Cottage

4425

1 bedroom, dog-friendly self-catering cottage in Royal Tunbridge Wells.


On the site of the 18th Century sawmill and on the common across the road from The Pantiles, Sawmill Cottage is ideally suited for couples wishing to explore the Royal Spa town of ...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £462

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 £500

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 £500

1 Thatched Cottage is a 2 bedroom thatched, self catering cottage with sea views in Seaview, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £521 *

1 Thatched Cottage

3508

2 bedroom thatched, self catering cottage with sea views in Seaview, Isle of Wight.


If the restorative power of the sea appeals to you, 1 Thatched Cottage with its uninterrupted views is an ideal holiday home. This 19th Century semi-detached property combines old ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £521 *

Jessie is a Luxury dog friendly Shepherds Hut near Battle.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £75 per night

Jessie

5231

Luxury dog friendly Shepherds Hut near Battle.


Jessie is a gorgeous shepherd's hut situated two hours from London, tucked away down a long meandering path in a paddock between crab apple and cherry trees, with views of the Suss...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £75 per night

Buckland Cabin is a 1 bedroom cabin near the beach in Seaview, Isle of Wight.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £545

Buckland Cabin

4853

1 bedroom cabin near the beach in Seaview, Isle of Wight.


Tucked away just off the High Street in Seaview, this recently renovated and beautifully presented cabin is ideal if you are seeking a romantic hideaway for two. Step inside th...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £545

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

Valdora is a 3 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £560 *

Valdora

4959

3 bedroom self catering cottage near the beach in Seaview, Isle of Wight.


Perfectly situated in the heart of the charming village of Seaview, Valdora is a gorgeous holiday retreat, beautifully styled to offer the very best in contemporary living. Seaview...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £560 *

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

From £85 per night

Douglas Fir

5290

Dog friendly shepherds hut near Pulborough.


Hidden away in the West Sussex countryside yet just two hours from London, this luxury shepherd's hut offers a magical escape for two. Beautiful and handcrafted, it has all you ...

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

From £85 per night

Load more

A sunny day in May can feel like summer, especially in South England. The schools have gone back. And the May calendar in the South West is bursting with high days, holidays and Pagan customs so peculiar you couldn't make them up. Have a peek at what's available. Use the search options on the left to choose the length of your break and the area where you want to stay. We've got 107 holiday cottages available in South England for your May escape.