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. 

We have 556 cottages that sleep 5 people

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

7 nights from £643

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


Right in the heart of Seaview village, this semi-detached property has been completely renovated, with a Skandi theme, to offer a wonderful place to stay on the Isle of Wight. With...

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

7 nights from £643

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

7 nights from £643 *

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


Lower Upcott farmhouse and its detached 'grand design' barn conversion housing a games-room and 'private cinema' TV-room together create a unique and breathtaking holiday property ...

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

7 nights from £643 *

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

7 nights from £649

3 bedroom holiday cottage with sea views in Mousehole, West Cornwall.


Beautifully refurbished, Pender Cottage occupies possibly one of the best positions in picturesque Mousehole. Watch the boats bob as the tide ebbs and flows, be lulled to sleep by ...

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

7 nights from £649

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £650

3 bedroom dog friendly cottage near the beach near Portscatho, South Cornwall.


This truly stunning Cornish cottage is located in a quiet terrace just off the square in the charming village of Portscatho only a short stroll from the shops, galleries, harbour, ...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £650

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £659

4 bedroom holiday cottage near the beach in Studland, Dorset.


The Isle of Purbeck is a stunning Area of Outstanding Natural Beauty between Poole and Swanage boasting one of the most spectacular coastlines in Dorset. Sunnyholme, an extremel...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £659

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £660

4 bedroom, dog friendly holiday cottage near Helford, West Cornwall.


A tranquil and secluded cottage in a beautiful rural location, offering complete privacy and wonderful views over The Lizard peninsula. This pretty cottage is only minutes from the...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £660

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

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £663

3 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight


A simply gorgeous three bedroom property just off St Helens' green on the eastern side of the Isle of Wight, The Haven is just a short walk from the coast and a ten minute stroll t...

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £663

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £679

3 bedroom holiday cottage in Corfe Castle, Dorset.


Situated in the popular Dorset village of Corfe Castle, on the Studland peninsula, close to the coast, this Grade II Listed picture-book cottage enjoys views of the spectacular Nat...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £679

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £685

Luxury safari tent glamping with a hot tub and sea views, pet friendly near Penzance.


Looking for the ideal retreat for a good old-fashioned family holiday? Then look no further – Mount View Sunrise Safari Tent is that and so much more. Set in the middle of its two ...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £685

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £685

Luxury safari tent glamping with a hot tub and sea views, pet friendly near Penzance.


Mount View Horizon Safari Tent is the perfect family retreat, set high above Mounts Bay in a spacious meadow with incredible 180 degree panoramic views. As far away from basic as i...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £685

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