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

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 47 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. 

Select from 47 Somerset cottages available for September

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

7 nights from £2354

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 £2354

Len's Hut is a Shepherds hut with hot tub and outstanding views near Wells, Somerset.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

From £150 per night

Len's Hut

2711

Shepherds hut with hot tub and outstanding views near Wells, Somerset.


Sitting in a peaceful meadow between the foothills of the Mendips and the serene landscapes of the Somerset Levels, beautifully crafted Len's Hut is the sweetest escape for two. ...

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

From £150 per night

The Cottage at Ford Barton is a 2 bedroom self catering cottage near Wellington, Somerset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Thu

7 nights from £1000

The Cottage at Ford Barton

5467

2 bedroom self catering cottage 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 (whi...

  • Sleeps 4 + cot
  • No pets
  • Changeover Thu

7 nights from £1000

Pippins is a 3 bedroom, dog friendly holiday cottage near Beaminster, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £607

Pippins

5360

3 bedroom, dog friendly holiday 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 £607

Green Place is a 1 bedroom, dog friendly self catering cottage in Wells, Somerset.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £527

Green Place

5313

1 bedroom, dog friendly self catering cottage 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 £527

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

7 nights from £1483 *

Springfields

5249

4 bedroom, dog friendly self catering cottage near Wells, Somerset.


Tucked away in the pretty countryside just outside of Wells and set over two floors, Springfields offers fresh and bright accommodation, with views over the surrounding fields. Sit...

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

7 nights from £1483 *

Jasmine Cottage is a 2 bedroom, dog friendly self catering cottage near Wells, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £582

Jasmine Cottage

5192

2 bedroom, dog friendly self catering cottage near Wells, Somerset.


Tucked away in the village of Stratton-on-the-Fosse, this delightful, terraced cottage is welcoming and quaint. Situated just off the Fosse Way; the ancient Roman road between Bath...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £582

Keepers Cottage is a 3 bedroom, dog friendly self catering cottage near Yeovil, Somerset.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £938

Keepers Cottage

5194

3 bedroom, dog friendly self catering cottage near Yeovil, Somerset.


Keepers Cottage is the former gamekeeper's cottage for Montacute House and is set in the rolling countryside of South Somerset, close to the historic village of Montacute. Stunning...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £938

We’re here to help you find your perfect place to stay 7 days a week.

Meadowbank is a 4 bedroom self catering cottage with sea views in Porlock, Somerset.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £919 *

Meadowbank

5187

4 bedroom self catering cottage with sea views in Porlock, Somerset.


In the perfect situation on the edge of the rugged Exmoor National Park and on the stunning West Somerset coastline, Meadowbank is a stylish and beautiful home from which to explor...

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

7 nights from £919 *

The Crook is a 1 bedroom shepherds hut near Ilminster, Somerset.
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £762

The Crook

5003

1 bedroom shepherds hut near Ilminster, Somerset.


Perfectly positioned in a peaceful spot, you will find this stunning shepherd's hut that has been masterfully created. The Crook is a true hideaway in glorious surroundings and you...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £762

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