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.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 927 holiday cottages available in September

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £975

5 bedroom, dog-friendly cottage near Mevagissey, South Cornwall.


This fabulous holiday house is beautifully furnished and superbly well-equipped, and provides plenty of space for everyone to spread out. With a bubbling hot tub in the garden-room...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £975

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  • 20% off

    30 Mar 2019 - 6 Apr 2019

    £924.63 £739.70

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1000

5 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight


This is a three-storey house right in the heart of Bembridge village, just opposite the picturesque village church and a few minutes' walk from the shops and restaurants. The prope...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1000

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1027

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


2 Little Cedars is a sleek and modern property, with a light and clean finish throughout. Split over three floors, and stylishly decorated with luxury furnishings, this delightful ...

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1027

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  • 20% off

    22 Mar 2019 - 29 Mar 2019

    £1026.77 £821.42

  • Sleeps 9 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1236

5 bedroom house with sea views in Bigbury-on-Sea, South Devon.


This wonderfully spacious house stands proud, perched on the edge of Sedgewell beach at Bigbury-on-Sea, the location of this house is second to none. Pond House doesn't just boast ...

  • Sleeps 9 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1236

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  • 20% off

    30 Mar 2019 - 6 Apr 2019

    £1186.07 £948.86

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1589

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


This impressive 150 year old Farmhouse sleeps nine and is the perfect location for a fabulous family gathering of all ages. In the breathtaking location of Barton Manor Estate, adj...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1589

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  • 20% off

    5 Apr 2019 - 12 Apr 2019

    £2072.45 £1657.96

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £761

5 bedroom, dog friendly holiday cottage near Holsworthy, North Devon.


The award-winning forest and countryside around Grascott House is magical: more than 200 almost uninhabited acres including woodland, wildflower meadows and three small, trout-stoc...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £761

Need more time? Reserve any cottage for up to 24 hours before booking.

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £823

5 bedroom, dog friendly holiday cottage with sea views in Wootton, Isle of Wight.


Creekside is a fabulous waterfront property that makes a wonderful choice of holiday home at any time of the year. This stunning detached house, set on the banks of Wootton Creek, ...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £823

View
  • 15% off

    22 Mar 2019 - 29 Mar 2019

    £822.82 £699.40

  • 15% off

    5 Apr 2019 - 12 Apr 2019

    £1088.06 £924.85

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £893

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


Swift Cottage is a gorgeous, comfortable Edwardian end-of-terrace property, spread over three levels with wooden flooring throughout the kitchen and dining area. The spacious dinin...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £893

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £895

4 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight


Orchard House is a wonderful property for an extended family looking for a sprawling holiday home near the beach in Bembridge. The downstairs living areas are inviting - no doubt t...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £895

  • Sleeps 10 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £975

5 bedroom, rural cottage near the beach in Portscatho, Cornwall.


Tucked away at the end of a Cornish country lane, this lovely old farmhouse is set in idyllic surroundings, overlooking adjacent farmland to the sea beyond. Imaginatively restor...

  • Sleeps 10 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £975

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