Holiday Cottages for September

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

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

We have 1176 holiday cottages available in September

Na Mara Bothy is a Off-grid dog friendly bothy with private beach and sea views near Oban.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £185 per night

Na Mara Bothy

5870

Off-grid dog friendly bothy with private beach and sea views near Oban.


For a touch of off-grid magic, look no further than this stunning escape with highlights including a private beach and gorgeous al fresco wood-fired bath. Set among the wilds of Ar...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £185 per night

Little Blue is a 1 bedroom, dog friendly cottage near the sea near Falmouth, Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £502

Little Blue

5864

1 bedroom, dog friendly cottage near the sea near Falmouth, Cornwall.


In the heart of the historic yet trendy town of Penryn and only a five minute drive to Falmouth is this perfect bolthole for two. Named one of the best towns to live in in the Sout...

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

7 nights from £502

Woodlane View is a 3 bedroom apartment near the beach in Falmouth, South Cornwall.
  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £945

Woodlane View

5861

3 bedroom apartment near the beach in Falmouth, South Cornwall.


A fabulous and spacious, three bedroom, ground floor apartment with a super garden, set in a great location in Falmouth with everything within easy reach. With glorious sandy beach...

  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £945

View
  • 20% off

    2 May 2025 - 9 May 2025

    From £1008.00 £806.40

  • 20% off

    9 May 2025 - 16 May 2025

    From £1069.00 £855.20

  • 20% off

    16 May 2025 - 23 May 2025

    From £1095.00 £876.00

The Ark is a Unique dog friendly houseboat, sleeping up to 12 guests in Torpoint, Cornwall.
  • Sleeps 12 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1586 *

The Ark

5873

Unique dog friendly houseboat, sleeping up to 12 guests in Torpoint, Cornwall.


Promising a stay like no other, The Ark is an exceptional mistress of the sea, a stately boat of epic proportions offering a home for 12 lucky sea mates. Docked just a stone’s thro...

  • Sleeps 12 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1586 *

Grove Villa is a 4 bedroom self catering cottage in Leyburn.
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1675

Grove Villa

5833

4 bedroom self catering cottage in Leyburn.


If a stunning property with original features along with contemporary design in the heart of a Yorkshire Dales market town sounds attractive then Grove Villa is the place for you. ...

  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1675

Pine Lodge is a Luxury cabin with a hot tub near Beccles, Norfolk.
  • Sleeps 2
  • No pets
  • Changeover Fri

From £139 per night

Pine Lodge

5848

Luxury cabin with a hot tub near Beccles, Norfolk.


Surrounded by the glorious countryside of the Norfolk Broads National Park, Pine Lodge is an idyllic retreat, beautifully crafted and cleverly designed with blissful views across n...

  • Sleeps 2
  • No pets
  • Changeover Fri

From £139 per night

Laurel Lodge is a Luxury cabin with a hot tub near Beccles, Norfolk.
  • Sleeps 2
  • No pets
  • Changeover Fri

From £150 per night

Laurel Lodge

5849

Luxury cabin with a hot tub near Beccles, Norfolk.


Nestled in the heart of the verdant countryside of the Norfolk Broads you will find the sweetest hideaway, Laurel Lodge, a beautifully crafted cabin with cosy interiors and a bliss...

  • Sleeps 2
  • No pets
  • Changeover Fri

From £150 per night

Orchard Barn is a 1 bedroom apartment with countryside views near Weston-super-Mare, Somerset.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £583

Orchard Barn

5855

1 bedroom apartment with countryside views near Weston-super-Mare, Somerset.


Tucked away in an enviable position, looking out over paddocks and apple orchards you will find Orchard Barn, a stylish apartment for two lucky guests. As soon as you arrive at thi...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £583

View
  • 20% off

    2 May 2025 - 9 May 2025

    From £587.00 £469.60

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

Number One Glassard is a 4 bedroom self catering cottage with sea views in Colonsay.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £750

Number One Glassard

5826

4 bedroom self catering cottage with sea views in Colonsay.


The moment you set foot on the pier or drive off the ferry, you'll know you have arrived somewhere very special. The lovely Isle of Colonsay, known colloquially as "gem of the sea"...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £750

Skapya Treehouse is a Luxury treehouse with hot tub in Gweek, Cornwall
  • Sleeps 2
  • No pets
  • Changeover Fri

From £220 per night

Skapya Treehouse

5858

Luxury treehouse with hot tub in Gweek, Cornwall


Surrounded by peaceful woodland in the charming Cornish hamlet of Gweek on the Lizard peninsula, Skapya is a beautifully crafted treehouse, hand-built from the finest cedar to blen...

  • Sleeps 2
  • No pets
  • Changeover Fri

From £220 per night

Load 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.