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 Sat

7 nights from £582

3 bedroom holiday cottage with sea views in Falmouth, South Cornwall.


There are superb views over Falmouth harbour from this lovely family house, perfect for watching the yachts, dinghies, cruise liners and naval ships out on the water and the coming...

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

7 nights from £582

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

7 nights from £584

3 bedroom thatched cottage near the beach in Instow, North Devon.


This beautiful and historic cottage is at the heart of the north Devon hamlet of Westleigh, just one mile from the stunning sandy beach at Instow. Plovers Barron is a listed 17th C...

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

7 nights from £584

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

7 nights from £586

3 bedroom, rural self catering cottage near Dartmouth, South Devon.


Eeyore's Cottage, once owned by Christopher Robin Milne, the son of Winnie the Pooh author A A Milne, has been beautifully restored. Found in the hamlet of Embridge, it is a 15 min...

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

7 nights from £586

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

7 nights from £587

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


Bay Cottage is a lovely three bedroom detached property on the outskirts of Seaview village, located in Seagrove Manor Road, a quiet spot yet just a few minutes walk into the villa...

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

7 nights from £587

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

7 nights from £592

3 bedroom self catering cottage with sea views in Seaview, Isle of Wight


A seaside sanctuary, Shore House is a three-storey beautifully decorated house, with its own private heated swimming pool. Making the most of the far reaching views over the Solent...

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

7 nights from £592

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £592

3 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.


This very pretty thatched cottage is in the tranquil historic village of Tolpuddle, surrounded by beautiful countryside and just 15 miles from the World Heritage Jurassic Coast. Wi...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £592

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

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

7 nights from £592

3 bedroom, rural cottage with sea views near Kingsand, Cornwall.


Situated in an acre of beautifully landscaped gardens in the heart of the Rame peninsula, with views across the rolling countryside to the waters of Plymouth Sound and Dartmoor in ...

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

7 nights from £592

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

7 nights from £592

3 bedroom, dog friendly cottage near the beach near St Mawes.


This lovingly updated 18th Century cottage is found in the picturesque village of St Just-in-Roseland, only a couple of miles from the beaches and sailing waters of St Mawes on the...

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

7 nights from £592

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

7 nights from £593

3 bedroom, dog friendly cottage with sea views in Portscatho.


Set in the lane that leads down to sandy Porthcurnick Beach where you will find the famous Hidden Hut beach cafe, Halcyon is an enticing destination for a coastal holiday. This spa...

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

7 nights from £593

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

7 nights from £595

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


Primrose Cottage is a fully modernised and beautifully furnished Victorian three bedroom cottage situated just off the green in St Helens and offering everything you might need for...

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

7 nights from £595

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