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 572 cottages that sleep 5 people

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £419

3 bedroom holiday cottage near Bridport, Dorset.


This sunny south-facing cottage enjoys a quiet rural position on the edge of the beautiful village of Netherbury, a short drive from the beaches and cliffs of the World Heritage Ju...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £419

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £421

3 bedroom self catering cottage near the beach in Brook.


September Cottage is an excellent, family-friendly holiday home with an expansive, attractive kitchen and good-sized kitchen, sitting and dining areas. It's easy to imagine curling...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £421

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £425

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


The location of 40 Trelawny Way, on a quiet residential road in Bembridge, belies its extravagant interior. For those looking for a family home with an interior decorated with arti...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £425

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

7 nights from £425

2 bedroom, dog friendly house with a pool near Perranporth, Cornwall


Nanteague House is semi-detached with its own south-facing sun-trap patio to the front, the perfect place for evening drinks as it overlooks the central courtyard and heated swimmi...

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

7 nights from £425

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  • 20% off

    20 Apr 2019 - 27 Apr 2019

    £531.30 £425.04

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £428

Gorgeous cottage style yurt sleeping 5 near Bude, Devon.


If you yearn for the romance of living under canvas but don't want to give up your creature comforts then this could definitely be the holiday for you. Situated close to the Cornwa...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £428

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

7 nights from £429

3 bedroom, dog friendly cottage with sea views in Sennen, Cornwall.


Perched above the harbour at Sennen Cove, Albatross is a stylish three-storey terraced retreat with wonderful sea views, perfect come rain or shine, as the roaring wood-burner in t...

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

7 nights from £429

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

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £431

3 bedroom, rural holiday cottage near Truro, South Cornwall.


Harvesters Keep is a gorgeous barn conversion set in a wonderfully tranquil location with fabulous far reaching views over rolling countryside. Just 10 minutes' drive from the pret...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £431

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

7 nights from £432

3 bedroom thatched, dog friendly cottage near Honiton, South Devon.


This gorgeous thatched cottage is in the beautiful Devon village of Broadhembury, a short drive from the east Devon and west Dorset Jurassic Coast with its chain of traditional coa...

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

7 nights from £432

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

7 nights from £436

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 £436

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £442

3 bedroom self catering cottage near Falmouth, West Cornwall.


A traditional Cornish cottage, Old Walls is set in the heart of the pretty village of Constantine, surrounded by the beautiful countryside of the north side of the Helford River. ...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £442

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