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 28 Somerset cottages available for September

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

7 nights from £1098 * booking fees included

The Cygnet - Lodge 11

6044

2 bedroom self catering cottage near Lyme Regis, Somerset.


Situated on the Cricket St Thomas estate and close to the borders of Somerset, Dorset and Devon, is The Cygnet - Lodge 11, a luxury Scandinavian style lodge. It is part of the sele...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £1098 *

The Old Dairy is a 2 bedroom, dog friendly self catering cottage near Taunton, Somerset.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £796 * booking fees included

The Old Dairy

6082

2 bedroom, dog friendly 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
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £796 *

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

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

7 nights from £771 booking fees included

The Byre

6066

1 bedroom self catering cottage near Taunton, Somerset.


**The Byre can accommodate flexible check in days – please contact us to request.** Located in the picturesque Blackdown Hills near the Somerset and Devon border you will find T...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £771

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

7 nights from £837 booking fees included

The Stables

6065

1 bedroom self catering cottage near Taunton, Somerset.


**The Stables can accommodate flexible check in days – please contact us to request.** Located in the famous Blackdown Hills near the Somerset and Devon border you will find The...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £837

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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 £830 booking fees included

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 £830

The Cottage at Ford Barton is a 2 bedroom cottage in the Blackdown Hills near Wellington, Somerset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £943 booking fees included

The Cottage at Ford Barton

5467

2 bedroom cottage in the Blackdown Hills near Wellington, Somerset.


Within the pretty Somerset village of Churchinford, this tranquil cottage has been furnished with comfort in mind. There is so much to explore locally with the Blackdown Hills Nati...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £943

Pippins is a 2 bedroom, dog friendly character cottage near Beaminster, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £539 * booking fees included

Pippins

5360

2 bedroom, dog friendly character cottage near Beaminster, Somerset.


Pippins is a picture postcard country cottage nestled in the charming Somerset village of North Perrott - not far from the Dorset border. This cosy home can cater for all of the fa...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £539 *

Green Place is a 1 bedroom, dog friendly cottage within walking distance of the cathedral in Wells, Somerset.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £501 booking fees included

Green Place

5313

1 bedroom, dog friendly cottage within walking distance of the cathedral in Wells, Somerset.


Wind your way through the historic streets of Wells to find Green Place nestling in a quiet mews offering a romantic getaway. With a vibrant and bustling high street, the city of W...

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

7 nights from £501

Wreath Farm

  • Sleeps 10 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1466.00 booking fees included

The Cowshed is a 2 bedroom, dog friendly cottage near Lyme Regis, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £675 * booking fees included

The Cowshed

4743

2 bedroom, dog friendly cottage near Lyme Regis, Dorset.


Nestled in the sleepy Somerset countryside, The Cowshed is a converted farm building, offering an excellent retreat. From the moment you arrive at this 'off the beaten track' setti...

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

7 nights from £675 *

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 28 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.