Holiday Cottages for September

Holiday Cottages for September

September is around the corner and a holiday in a self-catering cottage is beckoning. With the last of the summer sunshine, warm sea temperatures from months of hot weather and the crowds starting to dwindle, September is a fantastic time to enjoy a holiday in a home-from-home. Solo retreat, family holiday or gathering with friends, our cottages provide an idyllic base from which to enjoy a perfect getaway. Read more

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

We have 1275 holiday cottages available in September

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

7 nights from £896 *

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 £896 *

3 Kelly's Gardens is a 2 bedroom, dog friendly cottage near the beach in St Ives, Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £643 *

3 Kelly's Gardens

6056

2 bedroom, dog friendly cottage near the beach in St Ives, Cornwall.


Tucked away in the very heart of St Ives, 3 Kelly's Gardens is a charming two bedroom terraced cottage and is the perfect spot for couples or families looking to soak up the town's...

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

7 nights from £643 *

Rockfield Lodge is a 3 bedroom, dog friendly self catering cottage near Battle.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1001

Rockfield Lodge

6054

3 bedroom, dog friendly self catering cottage near Battle.


Situated in beautiful grounds just outside the medieval town of Battle and a short drive from Hastings and St Leonards-on-Sea, this delightful lodge offers a spacious holiday abode...

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

7 nights from £1001

The Police House is a 4 bedroom, dog friendly holiday cottage near the beach in Seaview.
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £898 *

The Police House

6051

4 bedroom, dog friendly holiday cottage near the beach in Seaview.


Perfectly situated in the heart of the charming village of Seaview on the stunning east coast of the Isle of Wight, The Police House is a delightful, detached holiday home located ...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £898 *

Darling Chestnut is a 1 bedroom self catering cottage near Helford, West Cornwall.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £925

Darling Chestnut

6009

1 bedroom self catering cottage near Helford, West Cornwall.


Resting under the ancient chestnut tree, not far from the oak-lined banks of the Helford, this beautifully converted detached barn has been curated into a dreamy retreat for two lu...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £925

Starry Skies is a 2 bedroom self catering cottage near Helford, West Cornwall.
  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1167

Starry Skies

6008

2 bedroom self catering cottage near Helford, West Cornwall.


Hidden away near the serene waters of the Helford River lies this thoughtfully renovated barn conversion and wild spa, where every detail has been crafted with care. From the soft-...

  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1167

Lighthouse Keeper's Cottage is a Stunning original Lighthouse Keeper's Cottage in enviable coastal location
  • Sleeps 10 + cot
  • Dogs welcome

Lighthouse Keeper's Cottage

169

Stunning original Lighthouse Keeper's Cottage in enviable coastal location


New for 2025! Lighthouse Keeper's Cottage is a truly unique and atmospheric place to stay, perched high above the sea on Douglas Head, one of the Isle of Man's most dramatic an...

  • Sleeps 10 + cot
  • Dogs welcome
Trewenna Cottage is a 4 bedroom, dog friendly cottage near the beach in Mullion, Cornwall.
  • Sleeps 9 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1636 *

Trewenna Cottage

6047

4 bedroom, dog friendly cottage near the beach in Mullion, Cornwall.


Gather family and friends to this spacious and welcoming home which is ideally situated on site within Cornwall's only Pony Club certified equestrian centre, just one mile from the...

  • Sleeps 9 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1636 *

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

Scrumpy Cottage is a 3 bedroom, dog friendly cottage near the beach in Mullion, Cornwall.
  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1462 *

Scrumpy Cottage

6048

3 bedroom, dog friendly cottage near the beach in Mullion, Cornwall.


Brimming with charm and unique kerb appeal, showcasing the craftsmanship of the stunning Blue Elvin stone, found only in two locations in the world, this beautifully crafted retrea...

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1462 *

Llawnroc is a 4 bedroom, dog friendly cottage near the beach in Mullion, Cornwall.
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £2256 *

Llawnroc

6049

4 bedroom, dog friendly cottage near the beach in Mullion, Cornwall.


Purpose-built and designed with intention by the thoughtful and experienced owners, this stunning holiday home is nothing short of a haven, curated for a family holiday that ticks ...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £2256 *

Load more

The beaches are inviting, the sea's had all summer to warm up and the schools have gone back, so make the most of quieter scenes still drenched in warm sunlight and give yourselves something to smile about. With our range of self-catering cottages, guests of all ages will settle straight in. Whether you are looking for a cottage nestled in the heart of lush countryside, a seaside sanctuary affording spectacular sea views or a town hub offering access to lots of local amenities, we will help you pave the way to your dream holiday this September. Offering a wide range of facilities, from enclosed gardens with barbecues, to homes with private swimming pools to properties with games rooms for kids, let your imagination run wild thinking about all the possibilities for your holiday in a Classic cottage. 

Holiday Cottages for September

At Classic Cottages we pride ourselves on marketing only the finest quality self-catering accommodation around. Combining the highest level of customer service with luxury cottages, we want your whole holiday to be the best it can be. Browse our portfolio for September and find your favourite now.