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 911 holiday cottages available in September

2 bedroom, rural holiday cottage near Chard, Somerset.


This high quality property is in a glorious rural setting in south Somerset, just a 20 minute drive from the stunning Jurassic coastline at Lyme Regis in Dorset. Purtington Barn Co...

  • Sleeps 3
  • Regret no pets
  • Changeover Fri

Price per week £447 - £612

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  • 15% off

    3 Aug 2018 - 10 Aug 2018

    £785.00 £667.25

  • 15% off

    10 Aug 2018 - 17 Aug 2018

    £785.00 £667.25

  • 15% off

    17 Aug 2018 - 24 Aug 2018

    £785.00 £667.25

2 bedroom, dog friendly holiday cottage near St Ives, West Cornwall.


Set in the peaceful hamlet of Mulfra, the nearby hills with sea views to both sides of Cornwall, Sixpenny Barn is a superb single-storey semi-detached cottage with footpaths leadin...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £460 - £618

2 bedroom, dog friendly cottage near Porthleven, West Cornwall.


With its own luxurious hot tub too, Daisy is just as immaculately presented as its neighbours. Inside, the light-filled living-room has glass doors opening onto the sunny deck, the...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sun

Price per week £469 - £611

2 bedroom holiday apartment with sea views in St Ives, West Cornwall.


Just a short walk to the beaches, restaurants and art galleries of St Ives, these luxurious gated apartments are stylish, contemporary and very comfortable. They have been designed...

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Sat

Price per week £738 - £984

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  • 20% off

    21 Jul 2018 - 28 Jul 2018

    £1620.00 £1296.00

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

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


Take a few steps up to the entrance, and you'll find yourself in 3 Kings House, a ground floor apartment in a small development. The property is just a short walk from Bembridge Ha...

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

Price per week £295 - £398

2 bedroom, dog friendly apartment near the beach near St Helens, Isle of Wight.


This two bedroom apartment in Bembridge is small but perfectly formed. Lovingly restored by the owners, 53a offers a perfect base for a family with a light and airy double bedroom ...

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

Price per week £295 - £450

View
  • 10% off

    27 Jul 2018 - 3 Aug 2018

    £695.00 £625.50

  • 20% off

    17 Aug 2018 - 24 Aug 2018

    £695.00 £556.00

2 bedroom, dog friendly apartment near the beach in Portscatho.


Jacaranda is a ground floor apartment with a bungalow apartment above Jacaranda Bungalow (3137), situated in an elevated position in a quiet cul-de-sac in the pretty fishing villag...

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

Price per week £295 - £341

2 bedroom self catering apartment with sea views in Seaview, Isle of Wight.


The Crow's Nest is a second floor apartment of a Victoria property in the historic village of Seaview. Simply furnished but with wonderful views over the village rooftops to the So...

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

Price per week £295 - £375

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


The perfect bolt-hole for families, 61 Drake Cottage is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview. Just yards from the ...

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

Price per week £309 - £444

View
  • 20% off

    21 Jul 2018 - 28 Jul 2018

    £670.00 £536.00

Our property managers are local experts who handpick perfect places to stay.

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