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 608 cottages that sleep 5 people

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

7 nights from £303

3 bedroom, rural holiday cottage near Ottery St Mary, South Devon.


This cheerful cottage is close to the east Devon village of Whimple, between Honiton and Exeter. It is a pretty and peaceful rural area surrounded by traditional apple orchards and...

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

7 nights from £303

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £317

2 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.


A deceptively spacious semi-detached Victorian property, Red House has a lovely large kitchen with both a breakfast-bar and a separate dining-area from which the enclosed garden ca...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £317

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

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £341

2 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.


A Victorian property set on a quiet road and yards from the beach. Oaks is a well-equipped property, decorated to a high standard and perfect for families with open plan seating an...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £341

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

7 nights from £344

3 bedroom self catering apartment near the beach in Seaview Isle of Wight.


1 The Saltings is a three-bedroom, lower ground floor apartment boasting a lovely beachfront location. It would ideally suit a family with children keen to enjoy the delights of th...

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

7 nights from £344

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

7 nights from £346

3 bedroom, rural holiday apartment near Marazion, West Cornwall.


The views from Moonbeam, across the countryside to St Michael's Mount and Mount's Bay, are wonderful. Relax on the south-facing balcony, wine in hand and enjoy the sound of silence...

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

7 nights from £346

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

7 nights from £359

2 bedroom self catering cottage at Island Harbour, near Newport.


Spring Tide is a delightful holiday cottage situated in a small development at Island Harbour Marina on the banks of the River Medina. The marina is set in a beautiful secluded val...

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

7 nights from £359

View
  • 20% off

    26 Jul 2019 - 2 Aug 2019

    £806.00 £644.80

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

7 nights from £361

3 bedroom self catering cottage in Buckfastleigh, Dartmoor.


An old weaver's cottage, dating back to early 1703 and Grade II Listed, Atlas Cottage is lovely and has low lintels and exposed beams as well as the original twisting wooden stairc...

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

7 nights from £361

View
  • 20% off

    26 Jul 2019 - 2 Aug 2019

    £784.00 £627.20

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £361

3 bedroom, dog friendly holiday cottage near Ivybridge, South Devon.


This charming retreat makes for the perfect adventurer's bolthole. Whether seeking out new and exciting destinations by car, or exploring this idyllic area on foot, this property i...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £361

Choose from our exclusive collection at the best prices with real time availability.

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £363

3 bedroom, dog friendly cottage near the beach in Praa Sands.


As its name suggests, this delightful cottage overlooks the pretty 14th Century church in the quaint village of Germoe and is only a mile from the child-friendly sandy beach at Pra...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £363

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

7 nights from £364

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


4A Ship House, an attractive townhouse positioned right in the middle of Seaview, is perfect for a family looking for a coastal break. 'Ship shape' in presentation, the fantastic t...

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

7 nights from £364

Loading more