May Half Term Holiday Cottages

May Half Term Holiday Cottages

With a cool breeze and warm sunshine, May marks the start of summer and many happy times to come. Kick start your summer properly and hop in the car; a holiday in a luxury self-catering cottage awaits. Browse through our list of 808 available cottages and find your favourite. All of our cottages are handpicked; personally inspected and fully equipped so your holiday is the best it can be.Read more

Spend your days exploring deep, green countryside and skim stones across lazy streams. Follow the scent of salty air and head to the coast, spending long days on the beach flitting between soft sands and cool sea. Perch on a bench and watch as life goes by, before heading to a local restaurant to dine on fresh, local produce lovingly crafted and prepared by skilled hands. Then, when you've had your fill of exploring, turn your attention to relaxing. Throw yourself into the holiday spirit and land in your own private self-catering cottage, primed and ready for you. An early summer break in your own slice of paradise can give you the chance to unwind, catch up and settle into a slower, more considered rhythm.  

Spend your May-Half Term in a Luxury Retreat

Whether you are looking for a solo retreat or want to bring the whole family away for a much-needed break, May half term provides ample opportunity to escape to greener grass for a while. However you'd like to spend your time, our cottages offer wide variety and consistent quality. Many of our cottages are dog-friendly too, meaning everyone can join in this May half term. 

Our exclusive ferry discounts will make your island trip with Classic plain sailing.

We have 808 cottages available for May half term

Shore House is a 3 bedroom self catering cottage with sea views in Seaview, Isle of Wight
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £1528

Shore House

3778

3 bedroom self catering cottage with sea views in Seaview, Isle of Wight


A seaside sanctuary, Shore House is a beautifully decorated three-storey house, with its own private heated swimming pool. Making the most of the far reaching views over the Solent...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £1528

Jubilee Cottage is a 2 bedroom holiday cottage near the beach in Coverack, West Cornwall.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £724

Jubilee Cottage

3770

2 bedroom holiday cottage near the beach in Coverack, West Cornwall.


One of the oldest cottages in the picturesque seaside village of Coverack, Jubilee Cottage has been beautifully and sensitively updated to the highest standard but still retains mu...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £724

Bussillion is a 3 bedroom holiday cottage with sea views in Falmouth, South Cornwall.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1231

Bussillion

3773

3 bedroom holiday cottage with sea views in Falmouth, South Cornwall.


What a fabulous holiday home this is, a gorgeous mix of early Victorian terraced townhouse elegance and 21st Century luxuries, topped off with superb panoramic views. Big bay w...

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

7 nights from £1231

Eastcott Cottage is a 4 bedroom, dog friendly holiday cottage near Bude, North Cornwall.
  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £973 *

Eastcott Cottage

3763

4 bedroom, dog friendly holiday cottage near Bude, North Cornwall.


Hidden away in the peaceful rural hamlet of Eastcott, within striking distance of the north Cornish coast and the Devon and Cornwall border, charming Eastcott Cottage is the finest...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £973 *

Little Linhay is a 2 bedroom, dog friendly self catering cottage in Ashburton, Dartmoor.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £940

Little Linhay

3730

2 bedroom, dog friendly self catering cottage in Ashburton, Dartmoor.


Little Linhay, a former hay barn stylishly converted into a stunning cottage, offers something very special. Set in a fabulous location within Dartmoor National Park, Little Linhay...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £940

2 Bermuda is a 2 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £668

2 Bermuda

3517

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


Welcome to 2 Bermuda, a rather lovely first floor apartment nestled in the charming village of Seaview, with wonderful views stretching across the Solent - ideal for an unforgettab...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £668

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

The Chalet on the Beach is a Chalet on the beach sleeping two in Lyme Regis, Dorset.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £634

The Chalet on the Beach

3351

Chalet on the beach sleeping two in Lyme Regis, Dorset.


Imagine a holiday right on the seashore of a very special beach, relaxing on your verandah with a glass of something refreshing, watching the gentle waves at one of the most famous...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £634

2 St Josephs is a 2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £863

2 St Josephs

3530

2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.


With sea views from the terrace and fresh, modern decor throughout, 2 St Josephs is a holiday maker's home-from-home. It is the perfect getaway for a small family, a couple or two ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £863

25 Palmerston Road is a 3 bedroom self catering cottage near the beach in Shanklin.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £841

25 Palmerston Road

3538

3 bedroom self catering cottage near the beach in Shanklin.


Welcome to 25 Palmerston Road, a delightful holiday home perfectly situated in the charming town of Shanklin and just a short stroll away from the golden sandy beach and a good sel...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £841

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

7 nights from £1014

30 Seaview Bay

3549

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


If you're searching for a place to stay by the sea, 30 Seaview Bay could be just the spot. Perched just steps away from the enchanting Seagrove Bay and Seaview Bay, this sunny apar...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £1014

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