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 46 holiday cottages available in September

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £340

1 Harrow Cottages

4642

1 bedroom self catering apartment near the beach in Seaview, Isle of Wight.


This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £340

View
  • 10% off

    8 Oct 2021 - 15 Oct 2021

    £340.00 £306.00

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

7 nights from £518

Jasmine Shepherd's Hut

3197

Shepherds Hut sleeping 2 with use of indoor pool and gym near Falmouth, South Cornwall.


Tucked down a country lane between the little county city of Truro and the sailing mecca of Falmouth, Jasmine is a lovely oak-built shepherd's hut from the renowned Somerset-based ...

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

7 nights from £518

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

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £543

The Byre

4732

1 bedroom self catering cottage near Battle.


Bursting with character and charm, The Byre is waiting to give you that rural experience. Situated in 12 acres of 1066 countryside it is one of Thornden Farm's original outbuilding...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £543

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £561

Tregwelan Shepherd's Hut

3819

Shepherds Hut with outstanding sea views near Padstow, North Cornwall.


"Wow!" will definitely be your first word when you arrive at gorgeous Tregwelan Shepherd's Hut. With spectacular views of the Camel Estuary and the delights of Padstow just a 20 mi...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £561

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £566 *

East Wells

4550

4 bedroom thatched holiday cottage near South Molton, North Devon.


East Wells is a wonderful, thatched, Grade II Listed farmhouse believed to date back to the 16th Century, situated on the fringes of Kings Nympton and benefitting from uninterrupte...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £566 *

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £585

The Lodge at Cobweb Cottage

4593

1 bedroom, dog friendly cottage near Frome, Somerset


Listen closely and you may just hear the lions at Longleat roar - now that would be a holiday memory with a difference! Tucked down a quiet lane just into Wiltshire, on the edge of...

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £585

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £596

La Cabine Francaise

4726

1 bedroom, dog friendly shepherds hut near Dorchester, Dorset.


Welcome to La Cabine Francaise, a glorious expanse of glamping bliss with a French twist. Set in the stunning Dorset countryside, this exclusive spot for two provides the perfect r...

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £596

View
  • 20% off

    2 Oct 2021 - 9 Oct 2021

    £744.94 £596.00

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £650

Temperance

4812

1 bedroom, dog friendly apartment near the beach in Freshwater, Isle of Wight.


Just a few minutes' walk from idyllic Freshwater Bay, Temperance is a real gem. A stylish and spacious first floor apartment, unwind into blissful island life where just a short wa...

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £650

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

From £120 per night

Dulcie

4809

1 bedroom self catering Gypsy Wagon near Bridgwater, Somerset.


Dulcie is a sweet vardo, Burton wagon nestled in a quiet corner of the owners' working farm in the stunning setting of Somerset's Quantock Hills - a 9,500 acre Area of Outstanding ...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

From £120 per night

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £849

Penelope

2965

1 bedroom, dog friendly apartment with sea views in Mullion.


This luxurious penthouse apartment has simply breathtaking views over Mullion Cove; perfect for that special break for two. Nestled into a rocky cove and sheltered by the stone har...

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £849

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