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. 

Isle of Wight Ferry Booking Our exclusive ferry discounts will make your island trip with Classic plain sailing.

We have 1038 holiday cottages available in September

Forge Cottage is a 3 bedroom self catering cottage near Mawgan Porth, North Cornwall.
  • Sleeps 5 + cot
  • No pets
  • Changeover Sat

7 nights from £554 *

Forge Cottage

4103

3 bedroom self catering cottage near Mawgan Porth, North Cornwall.


Set in the heart of the pretty village of St Mawgan and only a five minute drive from the golden sands and stunning coastline of Watergate Bay and Mawgan Porth; Forge Cottage is a ...

  • Sleeps 5 + cot
  • No pets
  • Changeover Sat

7 nights from £554 *

Ivy Cottage is a 2 bedroom, dog friendly cottage in Cattistock near Dorchester, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £644

Ivy Cottage

4122

2 bedroom, dog friendly cottage in Cattistock near Dorchester, Dorset.


Imagine life in a tranquil Dorset village and Ivy Cottage is just the sort of place you may picture in your mind. Set in the midst of an Area of Outstanding Natural Beauty (now ren...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £644

The Witch's Wagon at Warleggan is a Family size, dog friendly shepherds hut near Lostwithiel, South Cornwall with a hot tub
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £675 *

The Witch's Wagon at Warleggan

4090

Family size, dog friendly shepherds hut near Lostwithiel, South Cornwall with a hot tub


Fall under the spell of this stunning location with an unforgettable stay at the enchanting Witch's Wagon. Squirreled away in the pretty hamlet of Warleggan, yes it is a real place...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £675 *

Jays Cottage is a 2 bedroom, dog friendly holiday cottage near Modbury, South Devon.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £648

Jays Cottage

4117

2 bedroom, dog friendly holiday cottage near Modbury, South Devon.


Jays Cottage is a delightful friendly home-from-home situated in the 18th Century country estate of Colmer. The breathtaking locality of this cottage makes venturing out and about ...

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

7 nights from £648

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

The Old Manor House is a 5 bedroom, dog friendly cottage close to the beach near Lyme Regis.
  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £2296

The Old Manor House

4124

5 bedroom, dog friendly cottage close to the beach near Lyme Regis.


Less than half a mile from the World Heritage Jurassic Coast, The Old Manor House is a beautiful 16th Century, Grade II Listed house, full of character with a delightful enclosed g...

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £2296

Manor Barn is a 4 bedroom, dog friendly cottage near Wadebridge, North Cornwall.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £902 *

Manor Barn

4113

4 bedroom, dog friendly cottage near Wadebridge, North Cornwall.


Ideally placed for exploring all the treasures north Cornwall has to offer and less than a mile from the pretty village of St Tudy, this wonderful barn conversion is ideal for fami...

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

7 nights from £902 *

Scenic Bay is a Glamping pod with sea views near Penzance, West Cornwall.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £524

Scenic Bay

4062

Glamping pod with sea views near Penzance, West Cornwall.


Scenic Bay is a dream, set in a spacious meadow with a stunning view to match its name. This pretty pod is beautifully finished and kitted out for all of your holiday needs. There ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £524

Coastal Gaze is a Dog friendly glamping pod with sea views near Penzance, West Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £524

Coastal Gaze

4063

Dog friendly glamping pod with sea views near Penzance, West Cornwall.


This beautifully situated pod has outstanding 180 degree views across Mount's Bay, running from the Lizard peninsula in the east, with majestic St Michael's Mount in the middle to ...

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

7 nights from £524

Mount Lookout is a Dog friendly glamping pod with sea views near Penzance.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £681

Mount Lookout

4064

Dog friendly glamping pod with sea views near Penzance.


Mount Lookout does exactly what it says on the tin! You'll want for nothing at this cute-as-pie glamping pod, fully equipped for all of your holiday needs. Wonderfully fitted-o...

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

7 nights from £681

Mounts Bay Meadow Glamping

  • Sleeps 12 + 3 cots in 3 properties
  • Changeover Fri

7 nights from £1728

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

Loading more