Hampshire Holidays for a May Break

Hampshire Holidays for a May Break

Spring is springing and all around there is a flurry of activity as new life and colour blossom and bloom. May in Hampshire is a wonderful time of year, providing perfect timing for a week or two of unadulterated rest and relaxation. Book yourself a self-catering cottage in Hampshire in May and enjoy the holiday of a lifetime. All of our self-catering cottages are carefully selected so only the best make it onto our books. Read more

Put a spring in your step and take a holiday in Hampshire this May. Whether it be a short-break over a May bank holiday, a romantic week spent in your own private paradise or a family holiday spent with the kids this May half term, May provides ample opportunity to make the most of this wonderful county.

Holidays in Hampshire this May

As soon as you open the door to your very own Classic cottage, you will immediately feel your worries leave you behind. Throw your bags down and settle in, there's nothing left to do but exactly as you please.

When you book with Classic Cottages, you are guaranteed excellent customer service along with the highest quality self-catering accommodation. We want your whole holiday to be as relaxed and easy as possible, and pride ourselves on marketing the finest cottages around. With each of our cottages personally inspected and fully equipped, we take all the hassle out of your experience and will provide help every step of the way. 

We have 4 handpicked cottages in Hampshire for May

Moo Cottage is a 3 bedroom, dog friendly holiday cottage near the sea, near Lymington.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1589

Moo Cottage

5566

3 bedroom, dog friendly holiday cottage near the sea, near Lymington.


Waiting for you overlooking the Beaulieu River, with views across the Solent to the Isle of Wight, is Moo Cottage. A welcoming haven to while away the days; with a beautiful art ga...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1589

Myrtle Cottage is a 3 bedroom self catering cottage near Hamble.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £2324

Myrtle Cottage

5517

3 bedroom self catering cottage near Hamble.


Set on the banks of the River Hamble, this quintessential and fairy-tale cottage is the perfect waterside location for gatherings with friends or family. Dating back to the 18th Ce...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £2324

Tap Cottage is a 3 bedroom, dog friendly self catering cottage near Romsey
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1906

Tap Cottage

5417

3 bedroom, dog friendly self catering cottage near Romsey


Within the bustling village of Stockbridge, this contemporary cottage has been renovated to an exceptional standard. There is so much to explore locally; with sites such as Salisbu...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1906

Yachtsmans Cottage is a 2 bedroom, dog friendly cottage with views of the river in Lymington, Hampshire.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1572

Yachtsmans Cottage

3194

2 bedroom, dog friendly cottage with views of the river in Lymington, Hampshire.


A special ‘Just for Two’ rate (for the week) applies outside of school holidays, call us to book. Just moments from the water’s edge at Lymington, this semi-detached whitewashed...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1572