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 890 holiday cottages available in September

1 bedroom thatched self catering cottage near Sherborne, Dorset.


Pound Farm Cottage is a hidden gem; this listed thatched cottage has been thoughtfully renovated to create a spacious, stylish holiday home, retaining many of the original features...

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

Price per week £436 - £597

Luxury dog friendly glamping cabin with hot tub in Colyton, Devon


Snuggled into the hillside and reached on foot via an ancient orchard, this bespoke cabin is the ultimate rural retreat. Gaze at the stars through the window from your super-comfy ...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £442 - £574

1 bedroom, rural holiday cottage near Beaminster, Dorset.


Lottie’s Loft is a luxurious first floor barn conversion, a gorgeous bolthole surrounded by beautiful Dorset countryside. Exterior steps lead from the decking to a balcony with bes...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

Price per week £442 - £574

4 bedroom, rural cottage with sea views near Helston, West Cornwall.


Wallis Barn is a splendid barn conversion with its own enclosed garden and a tennis lawn for guests’ exclusive use. Climbing the original external stone stairs, you step into the s...

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

Price per week £445 - £912 *

* Includes 40% off for parties up to 2 + cot between 6 Jan and 8 Dec 2018. The ground floor is excluded at the discounted rate.

Shepherds Hut sleeping 5, dog friendly near Tiverton, North Devon.


Shepherd's Sky Super Hut is truly unique. This huge shepherd's hut, measuring 36' long, has been lovingly treated to a bespoke make-over, and offers two bedrooms at either end whic...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £451 - £830 *

* Includes 30% off for parties up to 2 + cot between 8 Sep and 13 Oct 2018. Only one bedroom is available at the discounted rate.

Shepherds Hut with hot tub, dog friendly near Bridgwater, Somerset.


Somerset's Quantock Hills - a nine and a half thousand acre Area of Outstanding Natural Beauty - rise up just behind the farm setting for this beautifully crafted, bespoke Shepherd...

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

Price per week £452 - £587

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

Dog friendly shepherds hut with hot tub near Bridgwater, Somerset.


At the heart of a farmstead in the Quantock Hills Area of Outstanding Natural Beauty, Duck's Puddle enjoys its own enclosed and private setting complete with a hot tub and little b...

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

Price per week £452 - £587

View
  • 10% off

    3 Aug 2018 - 10 Aug 2018

    £675.00 £607.50

1 bedroom, dog friendly self catering cottage near Wells, Somerset.


This converted single-storey barn is in a peaceful rural position on the edge of Somerset’s Mendip Hills, within easy reach of Bath, Bristol and Wells. The Barn is a perfect base f...

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

Price per week £459 - £596

1 bedroom, dog friendly cottage near the beach near Ilfracombe.


In the heart of pretty Berrynarbor village just half a mile from the beaches, harbours and cliffs of the north Devon coastline, Little Bessemer is the perfect holiday retreat. Idea...

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

Price per week £462 - £600

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


Tiddily Prom has unsurpassed sea views across Mount’s Bay as far as the Lizard peninsula. Elegant and spacious, this light and airy apartment has an open plan living area and a lar...

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

Price per week £464 - £605

View
  • 20% off

    27 Jul 2018 - 3 Aug 2018

    £852.00 £681.60

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