Luxury 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.

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 497 holiday cottages available in September

2 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight.


35 Cross Street is a cute end of terrace townhouse with accommodation spread over three floors, and has a sunny, enclosed courtyard. Built at the turn of the century, and decorated...

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

Price per week £303 - £436

2 bedroom self catering cottage near the beach in Seaview, Isle of Wight.


The Lobster Pot is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview and next to a nature reserve. This beach bolt hole has dec...

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

Price per week £312 - £437

2 bedroom, dog friendly holiday cottage in Beaworthy, South Devon.


This charming cottage is set within the most beautiful and tranquil countryside, offering numerous walks, breathtaking views and the ultimate in peace and quiet; this fabulous dog-...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

Price per week £313 - £503

View
  • 15% off

    28 Sep 2018 - 5 Oct 2018

    £367.65 £312.80

  • 15% off

    5 Oct 2018 - 12 Oct 2018

    £367.65 £312.80

  • 15% off

    12 Oct 2018 - 19 Oct 2018

    £367.65 £312.80

2 bedroom, rural self catering apartment near the beach in Ryde.


6 Sandlands is a modest top floor apartment with a large, open plan living area, just a stroll away from Ryde's wonderfully sandy beaches, the canoe lake and the children's sand pa...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

Price per week £313 - £433

2 bedroom, dog friendly holiday cottage near the beach in Ventnor, Isle of Wight.


With an interesting history and dating from 1852, Trevessa was once a fishing cottage and overlooks the sea. The sitting-room, dining-room and both bedrooms have beautiful sea view...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £314 - £612

View
  • 20% off

    19 Oct 2018 - 26 Oct 2018

    £611.62 £489.60

2 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight


Cockleshells is one of the charming Salterns bungalows situated along the Seaview Duver within a short walk to the Yacht Club and Seaview Village. The new Owner has completely rede...

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

Price per week £314 - £450

Don’t miss out; reserve your favourite 2019 holiday cottage for just £30

2 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.


Kitty Wake is a comfortable and neatly presented holiday bungalow located on the edge of the Salterns Holiday Village, in the charming village of Seaview. There are on site ameniti...

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

Price per week £329 - £579

2 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.


Wagtail is a comfortable and neatly presented holiday bungalow located on the edge of the Salterns Holiday Village, in the charming village of Seaview. There are on site amenities ...

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

Price per week £329 - £579

2 bedroom, dog-friendly holiday cottage with sea views in East Cowes, Isle of Wight


Smugglers' Run is a waterside property overlooking the River Medina and across to the sailing town of Cowes. Watch the boats sail by from the privacy of the balcony off the living-...

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

Price per week £337 - £495

2 bedroom self catering apartment near the beach in Ryde.


6 Pier View Court, perfectly located right on the seafront at Ryde, is a modern, well presented second floor apartment, tastefully decorated and furnished to a high standard. Relax...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

Price per week £344 - £479

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