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 807 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 807 cottages available for May half term

7 Sandpipers is a 3 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £858

7 Sandpipers

3568

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


Perfectly situated in the heart of the popular sailing village of Seaview on the eastern side of the Isle of Wight, 7 Sandpipers is a well-equipped town house set across three floo...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £858

Alcantara is a 3 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1263

Alcantara

3574

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


Beautifully decorated in neutral tones throughout, Alcantara is a well-presented, spacious property offering flexible family accommodation in the heart of Seaview. This detache...

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

7 nights from £1263

Choose our flexible booking option and have the ability to cancel anytime.

Blackberries is a 3 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £966

Blackberries

3583

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


A warm Isle of Wight welcome awaits you at Blackberries, a pretty coastal cottage which offers a peaceful escape for families, small groups or couples alike, in the delightful sail...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £966

Garsdon is a 4 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1229

Garsdon

3604

4 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.


This lovely bright and spacious detached house located on a quiet lane in Seaview is just a ten minute stroll from the beautiful beach at Seagrove Bay. With a charming large enclos...

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

7 nights from £1229

Lucaya is a 4 bedroom self catering cottage near the beach in Ryde, Isle of Wight.
  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £987

Lucaya

3621

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


Welcome to Lucaya, a smart town house for eight set over three floors, a great space with a pretty enclosed rear patio and lawn, the ideal stay for a family looking for a seaside b...

  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £987

Neptune Cottage is a 4 bedroom, self catering cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1829

Neptune Cottage

3636

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


Just a few steps from your front door to the sea, this stunning newly refurbished seafront cottage is an exceptional place to stay in Seaview. With many of the rooms boasting wonde...

  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1829

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

7 nights from £876

Pandora Lodge

3642

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


Perfectly situated in the heart of the delightful village of Seaview on the Isle of Wight, Pandora Lodge is a lovely, spacious ground floor apartment forming part of a larger prope...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £876

Quiet Corner Cottage is a 2 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £747

Quiet Corner Cottage

3646

2 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.


Bembridge is a much sought-after pretty village on the east of the Isle of Wight and Quiet Corner Cottage is a cosy semi-detached bungalow, perfectly situated just a mile from the ...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £747

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

Spinnakers is a 2 bedroom, dog friendly holiday cottage near the beach in Yarmouth, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £824

Spinnakers

3659

2 bedroom, dog friendly holiday cottage near the beach in Yarmouth, Isle of Wight.


A really lovely little bungalow, holding true to its seaside location with a nautical feel to the interior styling, semi-detached Spinnakers is situated on a small private estate w...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £824

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  • 50% off

    6 Dec 2024 - 13 Dec 2024

    £599.00 £299.50

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

7 nights from £737

Yardley

3697

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


Yardley is a charming Victorian cottage, set in the centre of the pretty sailing village of Seaview. The beach and local shops are only a few minutes from your doorstep making this...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £737

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