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 EnglandRead 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 142 holiday cottages available this May in South England.

Isle of Wight Ferry Booking Our exclusive ferry discounts will make your island trip with Classic plain sailing.

We have 142 self catering cottages available to rent in May in South England

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 £1113

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 £1113

The Studio is a 1 bedroom, dog friendly, cosy cottage near Ryde.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £440

The Studio

5753

1 bedroom, dog friendly, cosy cottage near Ryde.


Whether you seek relaxation or adventure on the Isle of Wight, The Studio provides the most welcoming modern-rustic retreat to experience the best of natural beauty and contemporar...

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

7 nights from £440

The Old Dairy

  • Sleeps 7 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1278

Bentinck is a 3 bedroom cottage near the beach in Ventnor.
  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £957

Bentinck

5724

3 bedroom cottage near the beach in Ventnor.


With everything you could wish for on your doorstep for a blissful Isle of Wight holiday experience with family or friends, Bentinck is a great base to explore all that this Island...

  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £957

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

7 nights from £721

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 £721

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 £604

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 £604

View
  • 15% off

    16 Nov 2024 - 23 Nov 2024

    £527.00 £447.95

  • 15% off

    23 Nov 2024 - 30 Nov 2024

    £527.00 £447.95

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 £1207

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 £1207

The Observatory is a 4 bedroom self catering apartment near the beach in Seaview.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1363 *

The Observatory

5693

4 bedroom self catering apartment near the beach in Seaview.


What a view! The most perfect seascape vistas will be found from this pretty apartment in the heart of the traditional seaside village of Seaview. This quirky home-from-home is the...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1363 *

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

Sunrise and Stars is a Dog friendly shepherds hut with a hot tub near Ventnor.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £102 per night

Sunrise and Stars

5672

Dog friendly shepherds hut with a hot tub near Ventnor.


Step into an oasis of peace and tranquility on the Isle of Wight at Sunrise and Stars, a beautifully crafted hideaway with a pool for private use and a hot tub, surrounded by capti...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £102 per night

Luffs Farm is a 5 bedroom, dog friendly self catering cottage near Battle.
  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1502

Luffs Farm

5653

5 bedroom, dog friendly self catering cottage near Battle.


Accessed via a narrow lane, this delightful farmhouse situated in 1066 country, has views over the valley towards the village of Sedlescombe. It makes an excellent retreat for fami...

  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1502

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