September Holidays in Somerset

September Holidays in Somerset

Squeeze out the last drops of summer and head to Somerset for an unforgettable holiday. Enjoy the September sunshine illuminating Somerset's beautiful landscapes and spend your days making the most of the late summer vibes. Then, when you are ready to turn in, return to your own slice of paradise in a luxury self-catering retreat.  Read more

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

Select from 40 Somerset cottages available for September

The Cygnet - Lodge 11 is a 2 bedroom self catering cottage near Chard, Somerset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £986 *

The Cygnet - Lodge 11

6044

2 bedroom self catering cottage near Chard, Somerset.


Situated close to the borders of Somerset, Dorset and Devon, is The Cygnet - Lodge 11, a luxury Scandinavian style lodge. It is part of the select Swandown gated development, which...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £986 *

Snowdrop Cottage is a 2 bedroom, dog friendly self catering cottage in Dulverton, Somerset.
  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £1165 *

Snowdrop Cottage

6072

2 bedroom, dog friendly self catering cottage in Dulverton, Somerset.


Every now and again a very special property comes along and Snowdrop Cottage is certainly it. Located just a short walk from the centre of Dulverton it's perfect for two or four gu...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £1165 *

The Old Dairy is a 2 bedroom self catering cottage near Taunton, Somerset.
  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £806 *

The Old Dairy

6082

2 bedroom self catering cottage near Taunton, Somerset.


The Old Dairy is a warm and cosy conversion set in the picturesque rolling hills of north Somerset. It offers spacious accommodation for up to four guests and will really strike a ...

  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £806 *

The Byre is a 1 bedroom self catering cottage near Taunton, Somerset.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £840

The Byre

6066

1 bedroom self catering cottage near Taunton, Somerset.


Located in the picturesque Blackdown Hills near the Somerset and Devon border you will find The Byre. A one bedroom converted cowshed which combines original character with modern ...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £840

The Stables is a 1 bedroom self catering cottage near Taunton, Somerset.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £840

The Stables

6065

1 bedroom self catering cottage near Taunton, Somerset.


Located in the famous Blackdown Hills near the Somerset and Devon border you will find The Stables. A luxurious one bedroom converted stable which combines original character with ...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £840

Florian is a Dog friendly converted shipping container with outdoor bath tub near Cheddar.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £776

Florian

5939

Dog friendly converted shipping container with outdoor bath tub near Cheddar.


This bijou beauty is just perfect for romantic getaways or for solo travellers seeking to escape the everyday. A stunning converted shipping container, it boasts idyllic countrysid...

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

7 nights from £776

The Smithy is a 2 bedroom, dog friendly holiday cottage near Glastonbury, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £629 *

The Smithy

5832

2 bedroom, dog friendly holiday cottage near Glastonbury, Somerset.


If a stunning conversion bursting with original features situated in a sleepy Somerset village sounds attractive then The Smithy is the place for you. Situated in close proximity t...

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

7 nights from £629 *

Wheelwrights Cottages

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1258

Yew Tree Barn is a 2 bedroom, dog friendly holiday cottage near Glastonbury, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £564 *

Yew Tree Barn

5784

2 bedroom, dog friendly holiday cottage near Glastonbury, Somerset.


Situated in a peaceful corner of Somerset, with uninterrupted countryside views across the Levels, Yew Tree Barn is a high quality barn conversion with a contemporary feel. Perfect...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £564 *

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

7 nights from £1952

Merryfields

5572

4 bedroom, dog friendly self catering cottage near Bath.


This spacious detached Victorian house is set on a two acre site in the rural village of Colerne, occupying a spectacular position over Box Valley with views of Salisbury Plain in ...

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

7 nights from £1952

Load more

If you are not quite ready to let summer go yet, book yourself a September holiday in Somerset. Last-minute or planned well in advance, a September getaway in Somerset will let you do your summer justice and leave you feeling relaxed and revived. Whether you are looking for a one-bed retreat, dog-friendly holiday cottage or big house with space enough for all the family and friends too, we will help you find the right cottage for you. With every one of our holiday cottages personally inspected and carefully selected onto our books, we make sure you can enjoy the best of the best. Browse our 40 cottages available for a September break in Somerset and let the good times commence. Your holiday with Classic Cottages will be so good you'll wish you could do it twice.