Cottages For May in Wiltshire

Cottages For May in Wiltshire

Shhh! Don’t tell too many people this but, if you’re looking for a cottage holiday in May you might have stumbled on one of the best months to visit Wiltshire Read more

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

We have 7 self catering cottages available to rent in May in Wiltshire

Kingfishers is a 1 bedroom, dog friendly holiday cottage near Shaftesbury, Dorset.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Mon

7 nights from £538

Kingfishers

6035

1 bedroom, dog friendly holiday cottage near Shaftesbury, Dorset.


Great care and attention has been put into this barn conversion, resulting in a truly cosy, yet spacious retreat for couples or solo travellers to enjoy. Located in Gillingham in n...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Mon

7 nights from £538

View
  • 20% off

    2 Feb 2026 - 9 Feb 2026

    £403.00 £322.40

  • 20% off

    9 Feb 2026 - 16 Feb 2026

    From £403.00 £322.40

  • 20% off

    16 Feb 2026 - 23 Feb 2026

    From £504.00 £403.20

  • 20% off

    23 Feb 2026 - 2 Mar 2026

    £403.00 £322.40

The Gatehouse is a 2 bedroom self catering cottage in Malmesbury.
  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £784 *

The Gatehouse

6033

2 bedroom self catering cottage in Malmesbury.


If ever a property was the epitome of luxury town living, then The Gatehouse is it. Located in the historic market town of Malmesbury it provides the perfect base for couples or fa...

  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £784 *

View
  • 20% off

    23 Jan 2026 - 30 Jan 2026

    From £560.00 £448.00

  • 20% off

    6 Feb 2026 - 13 Feb 2026

    From £560.00 £448.00

  • 20% off

    13 Feb 2026 - 20 Feb 2026

    From £728.00 £582.40

  • 20% off

    20 Feb 2026 - 27 Feb 2026

    From £616.00 £492.80

Weighbridge End is a 1 bedroom, dog friendly self catering cottage near Chippenham.
  • Sleeps 2 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £694

Weighbridge End

5647

1 bedroom, dog friendly self catering cottage near Chippenham.


This stunning barn located on the edge of the Cotswolds is a gem of a property just waiting to be discovered. Sympathetically converted with nods to its previous life as a working ...

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

7 nights from £694

Stable End is a 1 bedroom, dog friendly self catering cottage near Chippenham.
  • Sleeps 2 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £694

Stable End

5648

1 bedroom, dog friendly self catering cottage near Chippenham.


Located in Grittleton, a short drive from both Chippenham and Bath, just on the edge of the Cotswolds, an area of beautiful countryside and picturesque villages, come and discover ...

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

7 nights from £694

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Weighbridge Barn

  • Sleeps 4 + 4 cots in 2 properties
  • Changeover Fri

7 nights from £1388

2 West Nolands is a 4 bedroom, dog friendly home close to  Avebury.
  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £914 *

2 West Nolands

5603

4 bedroom, dog friendly home close to Avebury.


Within an hour of the beautiful city of Bath and if you tire of the local landscape, the south Cotswolds and the New Forest are close enough for a day trip. Your four-legged friend...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £914 *

Hatts Barn is a 2 bedroom, rural holiday cottage near Shaftesbury, Dorset.
  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £889

Hatts Barn

2093

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Hatts Farm is a working farm located in a National Landscape. The farm spreads over 150 acres, located in the stunning countryside of the Dorset and Wiltshire border. Hatts Barn...

  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £889

Spring is in full swing, it is often one of our sunniest months and some of the best local festivals start. And you get the pick of the properties in Wiltshire. So have a look through our 7 holiday cottages available this May in Wiltshire.