May half term holiday cottages

May half term holiday cottages

With a cool breeze and the hint of summer on its way, May is a wonderful time of year to discover a beautiful corner of the UK.Read more

With the summer holidays still out of reach and warmer weather on its way, why not take advantage of this lovely time of year and escape to South England. Travel solo, have a romantic getaway, or take advantage of some true family time and have a half term to remember in a cottage this half term, get ready to make memories you’ll keep forever.

We've got 38 holiday cottages matching your search in the South of England...

Kingston Barns

  • Sleeps 11 + 3 cots in 3 properties
  • Changeover Sat

7 nights from £2432

Windy Ridge is a 4 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2405

Windy Ridge

4464

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


Tucked away in the idyllic setting of Seagrove Bay and just steps away from the beach, Windy Ridge is a stunning semi-detached house with wonderful sea views from both the ground a...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2405

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 £552

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 £552

Winkle Cottage is a 2 bedroom self catering cottage near the beach in Cowes, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £833

Winkle Cottage

4395

2 bedroom self catering cottage near the beach in Cowes, Isle of Wight.


This gorgeous terraced cottage, situated in the Conservation Area of the old town of Cowes, is just a few minutes walk from the centre of town, offering the perfect family holiday ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £833

Solent View Cottage is a 2 bedroom self catering cottage near the beach in Cowes, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £738

Solent View Cottage

4389

2 bedroom self catering cottage near the beach in Cowes, Isle of Wight.


This charming two bedroom cottage is situated in the pretty coastal village of Gurnard just outside Cowes, home to some spectacular Solent views and a prime location to watch the m...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £738

Fortune is a 4 bedroom, dog friendly holiday houseboat with sea views in Bembridge, Isle of Wight
  • Sleeps 8
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1989

Fortune

4336

4 bedroom, dog friendly holiday houseboat with sea views in Bembridge, Isle of Wight


Step on board this simply stunning houseboat situated in the picturesque Bembridge harbour, just a short walk from Bembridge village. The beautiful bright yellow door opens to a va...

  • Sleeps 8
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1989

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

Buckland House is a 4 bedroom self catering cottage near the beach in Seaview, Isle of Wight
  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1677

Buckland House

4290

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


Tucked out of sight yet right in the heart of Seaview, Buckland House is a stunning home, beautifully renovated by the owners and just a stone's throw from the beach and local vill...

  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1677

View
  • 15% off

    24 May 2024 - 31 May 2024

    £2516.00£2138.60

Grace Cottage is a 1 bedroom, dog friendly holiday cottage near the sea near Ventnor, Isle of Wight
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £700

Grace Cottage

4209

1 bedroom, dog friendly holiday cottage near the sea near Ventnor, Isle of Wight


This gorgeous barn conversion is set within the grounds of the stunning North Grounds Farm, just outside the village of Chale Green on the southern side of the Island. For the envi...

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

7 nights from £700

Flackstead is a 3 bedroom self catering cottage near the beach in Brook, Isle of Wight
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2862

Flackstead

3913

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


Flackstead is a unique eco-friendly house which has breathtaking and uninterrupted coastal views across Compton Bay towards the Needles. Flackstead combines the very best of co...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2862

Bay View is a 2 bedroom, rural holiday apartment near the beach in Freshwater, Isle of Wight
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £1087

Bay View

3902

2 bedroom, rural holiday apartment near the beach in Freshwater, Isle of Wight


This beautiful contemporary apartment is literally perched above the beach, offering stunning views of the picturesque Freshwater Bay. Extremely well appointed, the apartment offer...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £1087

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