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

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. 

We have 1137 holiday cottages available in September

The Little Dairy Park Farm is a 2 bedroom, dog friendly holiday cottage near Ryde, Isle of Wight.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £694

The Little Dairy Park Farm

5636

2 bedroom, dog friendly holiday cottage near Ryde, Isle of Wight.


This welcoming retreat is close to the pretty village of Seaview and the sandy beach at Ryde, and has the Isle of Wight Gin Distillery within walking distance. Thoughtfully present...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £694

Woodlands is a 5 bedroom, dog friendly holiday cottage in Exmouth, South Devon.
  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1836

Woodlands

5623

5 bedroom, dog friendly holiday cottage in Exmouth, South Devon.


Introducing a super family-friendly home, lovingly furnished and equipped to offer that perfect venue for any special celebration or multigenerational family holiday. Woodlands off...

  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1836

The Boathouse is a 2 bedroom, dog friendly cottage with sea views near Helford.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £867

The Boathouse

5553

2 bedroom, dog friendly cottage with sea views near Helford.


Sheltering under a canopy of oak foliage, this former boathouse rests at the water's edge on the tranquil banks of the Helford River. It has been lovingly yet sympathetically resto...

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

7 nights from £867

The Barn By The Ford is a 1 bedroom thatched, dog friendly cottage near Chipping Norton.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £739

The Barn By The Ford

5609

1 bedroom thatched, dog friendly cottage near Chipping Norton.


Step into the charm of rural living with this meticulously converted one bedroom barn located in the idyllic village of Middle Barton. With its blend of rustic architecture and mod...

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

7 nights from £739

Strand Causeway is a 3 bedroom holiday cottage with sea views near Exeter, South Devon.
  • Sleeps 5 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £766 *

Strand Causeway

5571

3 bedroom holiday cottage with sea views near Exeter, South Devon.


Introducing a very special Topsham house indeed. Steeped in history and nestled on the riverbank of the river Exe. Boasting oodles of charm and external space, two private parking ...

  • Sleeps 5 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £766 *

Sophie's Cottage is a 1 bedroom, dog friendly cottage near the beach near Portscatho.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £828

Sophie's Cottage

5616

1 bedroom, dog friendly cottage near the beach near Portscatho.


Nestled in the pretty hamlet of Treworthal this delightful semi-detached thatched cottage is a real gem. Come and stay at this lovely Grade II Listed stone cottage to enjoy everyth...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £828

The Shepherds Rest is a 1 bedroom self catering cottage near Dartmouth, South Devon.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £578

The Shepherds Rest

5620

1 bedroom self catering cottage near Dartmouth, South Devon.


If you are looking for a luxury rural retreat for two, surrounded by the most glorious countryside and only a short distance from the renowned naval town of Dartmouth, look no furt...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £578

St Brides Cottage is a 2 bedroom, dog friendly holiday cottage near the beach near Dale.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £632

St Brides Cottage

5640

2 bedroom, dog friendly holiday cottage near the beach near Dale.


Explore the spellbinding beaches, craggy cliffs and wildlife-filled islands in Pembrokeshire from St Brides Cottage, a gorgeous single-storey barn conversion, with a heavenly Scand...

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

7 nights from £632

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

Orchard View is a 2 bedroom, dog friendly self catering cottage near Leominster
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1446

Orchard View

5618

2 bedroom, dog friendly self catering cottage near Leominster


If you are looking for a true country escape with the most delightful farmhouse features and a healthy dose of local history, Orchard View won't disappoint. This meticulously re...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1446

The Shack is a 1 bedroom, dog friendly holiday cottage with sea views in Cowes.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1045

The Shack

5634

1 bedroom, dog friendly holiday cottage with sea views in Cowes.


Overlooking the waters of the Solent, start your mornings on the front deck admiring the view whilst deciding how to spend your day. Instantly relax into your holiday and breathe i...

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

7 nights from £1045

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