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

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

We've got 7 holiday cottages matching your search in Kent...

Bloomsbury Cottage is a 1 bedroom, dog friendly self catering cottage in Wadhurst.
  • Sleeps 2 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £678 booking fees included

Bloomsbury Cottage

6186

1 bedroom, dog friendly self catering cottage in Wadhurst.


For a digital detox head to the beautiful countryside of the High Weald National Landscape to stay at this unique timber-cladded barn that offers a peaceful escape just moments fro...

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

7 nights from £678

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

7 nights from £1393 booking fees included

Dunks Cottage

6074

4 bedroom, dog friendly self catering cottage near Cranbrook.


Overlooking the village green of Sandhurst, Kent, in the beautiful High Weald National Landscape (Area of Outstanding Natural Beauty), this wonderfully spacious, semi-detached cott...

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

7 nights from £1393

We are Gold accredited with the Green Tourism Business Scheme.

Pump Cottage is a 2 bedroom self-catering cottage in Rye.
  • Sleeps 3 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £546 booking fees included

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 £546

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 £703 booking fees included

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 £703

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British Travel Awards 2025
Best company for UK holiday home rentals

4 Church Square is a 1 bedroom, dog friendly self catering cottage in Rye.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £750 booking fees included

4 Church Square

5520

1 bedroom, dog friendly self catering cottage in Rye.


Welcome to this gorgeous Grade II Listed cottage situated along one of Rye's famous cobbled streets, perfect for couples looking to stay in the heart of Rye. As you enter this ...

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

7 nights from £750

Weald View Cottage is a 2 bedroom self catering cottage near Maidstone.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £735 booking fees included

Weald View Cottage

5284

2 bedroom self catering cottage near Maidstone.


Perfectly situated in the heart of the Kent countryside, this pretty semi-detached cottage with spectacular views across the Kent Weald is ideally located for walkers, couples and ...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £735

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 £650 booking fees included

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 £650

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 Kent. 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.