Holiday Cottages for 5 People

Holiday Cottages for 5 People

Gather your family or herd up your friends, a holiday in a luxury self-catering cottage for 5 people awaits. Providing the perfect base for adventure in the day and offering total comfort for long afternoons and evenings relaxing together, our cottages combine home-comforts with modern luxuries. Secure your favourite now and get ready to make memories to last a lifetime. Read more

There's no better time to secure your dream holiday cottage than the present. Cosy winter breaks help vanquish the winter blues and summer getaways provide the subject for photo albums packed with happy memories. Out of season holidays are great for both short breaks and longer holidays, providing tranquillity away from busier times. Book a spontaneous short break and then pencil in a longer holiday to look forward to. With so many beautiful places to visit and luxury cottages to choose from, you'll be spoilt for choice.  

Whether you're looking for a rural retreat in the heart of lush countryside, a seaside bolthole with stunning ocean views, or a town hub combining home-comforts with great access to local amenities, we'll help you find a holiday cottage that ticks all the boxes. From quaint thatched cottages to clifftop nests, our self-catering properties are diverse in nature and consistent in quality.

Holiday Cottages for 5 People

At Classic Cottages, we pride ourselves on marketing only the highest quality cottages. Understanding the importance of accommodation in making or breaking your holiday, we ensure only the best cottages are on our books. Regularly inspected and fully equipped with everything you could need and more, holidays with Classic Cottages takes the stress out of your whole experience. 

Our exclusive ferry discounts will make your island trip with Classic plain sailing.

We have 707 cottages that sleep 5 people

The Enchanted Wardrobe at Warleggan is a Dog friendly shepherd hut with hot tub near Lostwithiel, South Cornwall.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £581

The Enchanted Wardrobe at Warleggan

4351

Dog friendly shepherd hut with hot tub near Lostwithiel, South Cornwall.


The Enchanted Wardrobe is stuff that dreams are made of - a holiday here will transport you to the magical land of Narnia - no, really! The pretty hamlet of Warleggan is twinned wi...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £581

Fred’s House is a 3 bedroom, dog friendly cottage near the beach near Looe, Cornwall.
  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £582

Fred’s House

2142

3 bedroom, dog friendly cottage near the beach near Looe, Cornwall.


There are tantalising glimpses of the sparkling waters of Talland Bay through the trees surrounding Fred's House, where the big sheltered garden is perfect for outdoor meals and th...

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £582

Be in the know… Sign up to our newsletter for holiday inspiration, offers and all things Classic.

School House is a 3 bedroom, dog friendly self catering cottage near the sea in Muston near Filey.
  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £588

School House

5704

3 bedroom, dog friendly self catering cottage near the sea in Muston near Filey.


This charming gem of a cottage is located in the pretty village of Muston, Yorkshire, which is listed in the Domesday Book. Close to the seaside town of Filey and one of England's ...

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £588

Seaglass is a 3 bedroom, dog friendly cottage near the beach in Portscatho.
  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £590

Seaglass

4939

3 bedroom, dog friendly cottage near the beach in Portscatho.


Portscatho is a charming unspoilt village in the heart of the beautiful Roseland peninsula and Seaglass sits in an enviable position at the head of a quiet and peaceful cul-de-sac,...

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £590

Quince Cottage is a 3 bedroom, dog friendly cottage close to the beach near Bridport, Dorset.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £598

Quince Cottage

5190

3 bedroom, dog friendly cottage close to the beach near Bridport, Dorset.


With the World Heritage Jurassic Coast within one mile's walk, Quince Cottage is a welcoming home in the pretty West Dorset village of Chideock. This charming home is the perfect l...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £598

Fairfield is a 3 bedroom self catering cottage near Kingsbridge, South Devon.
  • Sleeps 5 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £600

Fairfield

4877

3 bedroom self catering cottage near Kingsbridge, South Devon.


Welcome to Fairfield, a light and airy getaway tucked away in the pretty village of Chillington which lies in the gorgeous south Devon Area of Outstanding Natural Beauty. With the ...

  • Sleeps 5 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £600

Tidal Waters is a 3 bedroom, dog friendly cottage with sea views near Fowey, Cornwall.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £601

Tidal Waters

5668

3 bedroom, dog friendly cottage with sea views near Fowey, Cornwall.


Escape on an enchanting creekside vacation, in this heavenly homestay for five in the darling hamlet of Penpol. Boasting an unrivalled location in a National Landscape (formerly kn...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £601

Lowenna is a 3 bedroom, dog friendly cottage near the beach in Portscatho.
  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £601

Lowenna

3133

3 bedroom, dog friendly cottage near the beach in Portscatho.


Lowenna is a delightful semi-detached barn conversion with Bryher (3132) next door. Perfect for families, it is located in a lovely rural setting just a five minute walk from Porth...

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £601

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

3 Pebble Cottage is a 3 bedroom, dog friendly cottage near the beach in Brixham, Devon.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £605

3 Pebble Cottage

5122

3 bedroom, dog friendly cottage near the beach in Brixham, Devon.


Just a hop, skip and a jump away from the pretty harbourside and many delights of vibrant Brixham on the English Riviera, Pebble Cottage is a traditional seaside cottage, perfect f...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £605

Hatts Barn is a 2 bedroom, rural holiday cottage near Shaftesbury, Dorset.
  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £615

Hatts Barn

2093

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Hatts Farm is a working farm located in a National Landscape. The farm spreads over 150 acres, located in the stunning countryside of the Dorset and Wiltshire border. Hatts Barn...

  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £615

Loading more