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 960 holiday cottages available in September

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1295

4 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


Set within a converted Victorian villa, Eversley Apartment is a large, contemporary split level apartment. With modern furnishings, this property offers a luxury option for a coast...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1295

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1305

4 bedroom, dog friendly cottage near the beach in Branscombe, Devon.


Set in its own mature gardens on a south-facing hillside, Barnell Cottage has views over Branscombe Vale and out to the World Heritage Jurassic Coast at Branscombe mouth. This beau...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1305

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1350

4 bedroom self catering cottage near the beach in St Helens, Isle of Wight


This absolutely stunning barn conversion is a little slice of luxury just outside the village of St Helens, only a short stroll to the St Helens Duver, sand dunes, beach and the Ba...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1350

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1364

4 bedroom thatched, dog-friendly cottage near South Molton, Devon.


Hidden deep in the truly peaceful, unspoilt north Devon countryside, in the grounds of an historic castle, lies Affeton Barton; a 16th Century farmhouse, newly renovated to a very ...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1364

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

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1395

3 bedroom self catering apartment with sea views in Shanklin, Isle of Wight.


Cromwell Apartment is a high end, beautifully presented, first floor apartment in a Victorian villa in Shanklin. Not your average beachfront apartment, the Cromwell comes with a de...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1395

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1500

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


This pretty attached Victorian cottage sits in the grounds of the Priory Estate and comes with use of its many diversions. With 70 acres of grounds to explore, plus a stunning priv...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1500

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  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £999.96 £799.97

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1500

4 bedroom self catering cottage with sea views in Seaview, Isle of Wight


A spectacular waterfront three-storey house situated on Seaview duver with uninterrupted sea views from the kitchen/dining-room and the first floor balcony. Just a few steps from y...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1500

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1600

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


This beautiful house is set in several acres of garden on the outskirts of Yarmouth, just a few minutes walk to the water’s edge, a truly stunning holiday destination. The property...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1600

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1829 *

4 bedroom holiday cottage with sea views in St Mawes, South Cornwall.


This impressive, recently-built eco-house is situated in a commanding elevated position on one of St Mawes' most exclusive roads. Enjoying panoramic sea views over the whole of Fal...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1829 *

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

7 nights from £723

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


6 Seafield Terrace is a charming, spacious terraced cottage set in the pretty village of Seaview. It would ideally suit a large family, several couples or a group of friends travel...

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

7 nights from £723

We’ve been raising the standards of self catering holidays since 1977.

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