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 493 holiday cottages available in September

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


23 Tollgate Cottages is a comfortably furnished beach bungalow located in a small, gated waterside development on the edge of Seaview, within walking distance to the shops and cafe...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £351 - £487

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


5 Sandpipers is a well equipped modern house set within a small development in the heart of Seaview, and offers comfortable accommodation for couples and families. Enjoy al fresco ...

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

Price per week £353 - £490

2 bedroom self catering apartment near the beach in Seaview.


A spacious, stylish, ground floor apartment in the sought-after Springfield Court complex, Apartment 4 offers guests the shared use of eight acres of mature landscaped grounds, a t...

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

Price per week £366 - £517

2 bedroom self catering cottage with sea views in Ventnor, Isle of Wight


Located in the cosmopolitan town of Ventnor in a Victorian town house, Seascape is a modern two bedroom apartment with spectacular sea views along the coastline. It offers contempo...

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

Price per week £368 - £564

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

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


A barn conversion in a rural setting, you'll enjoy a feeling of peace from the moment you step inside this lovely retreat, with its exposed beams and rustic decor. Sitting within t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £369 - £495

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


Fir Cottage is an attractive and contemporary conversion of a Victorian home, located right in the heart of St Helens. The village green (England's second largest) lies a few yards...

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

Price per week £373 - £554

2 bedroom self catering apartment near the beach in Ryde.


With spectacular views of the Solent, 3 Windsor House is a neutrally decorated second floor apartment with simple, modern furnishings, just yards from the beach and a short walk in...

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

Price per week £374 - £592

2 bedroom, rural self catering cottage Iddesleigh, North Devon.


This peaceful detached barn conversion is off the beaten track yet easy to reach, with Dartmoor National Park a short distance to the west and just a few miles from a scenic route ...

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

Price per week £374 - £503

2 bedroom self catering cottage with sea views in Seaview.


North View is a wonderful holiday hideaway just on the outskirts of Seaview with sea views across the Solent from the kitchen/dining-room and first floor bedrooms. Set back from th...

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

Price per week £375 - £675

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


Originally the farm's milking parlour, this delightful cottage sleeping four is the perfect cottage to spend quality time together as a family in a stunning rural location. Located...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £378 - £534

Our guests rate us 4.8/5 on Feefo, the independent review site.

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