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 563 cottages that sleep 5 people

  • Sleeps 5
  • Regret no pets
  • Changeover Sat

7 nights from £505

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


Situated in an enviable position overlooking the Atlantic Ocean and just a few hundred yards from the stunning sands of Sennen Cove, Oystercatcher (formerly known as The Bosun's Lo...

  • Sleeps 5
  • Regret no pets
  • Changeover Sat

7 nights from £505

View
  • 20% off

    30 Mar 2019 - 6 Apr 2019

    £630.99 £504.79

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

7 nights from £505

3 bedroom, rural self catering apartment near the beach near Newport, Isle of Wight


This stunning barn conversion is located just outside the picturesque village of Chillerton, in the heart of the Island’s farming community between Newport and Chale. The outlook o...

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

7 nights from £505

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

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

7 nights from £515

3 bedroom apartment with sea views in Falmouth, South Cornwall.


Superb views over the water to Flushing and the Roseland peninsula are guaranteed from this beautifully decorated contemporary first floor apartment, part of the renowned Admiral's...

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

7 nights from £515

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £518

3 bedroom, dog friendly self catering cottage in Ventnor.


This gorgeous stone cottage is nestled in a wonderful countryside location in the central south of the Island, a short distance from the coastal town of Ventnor. Situated at the en...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £518

View
  • 10% off

    20 Apr 2019 - 27 Apr 2019

    £575.04 £517.50

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

7 nights from £520

3 bedroom, dog friendly cottage near the sea in Boscastle, Cornwall.


Boscastle needs little introduction, its picturesque harbour being a well-known Cornish landmark. A mere two minute stroll back from the fishing boats, tucked below the harbour...

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

7 nights from £520

  • Sleeps 5 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £522

2 bedroom, dog friendly holiday cottage near Tavistock, Dartmoor.


Found in rolling Devon farmland in an Area of Outstanding Natural Beauty a mile from Dartmoor, this delightful detached property at Lower Chaddlehanger has far reaching views towar...

  • Sleeps 5 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £522

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

7 nights from £522

3 bedroom holiday cottage near the beach near St Ives, West Cornwall.


Rosedale is a traditional detached cottage which enjoys a fantastically convenient location set back slightly from the main road leading to the famously popular St Ives, its wonder...

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

7 nights from £522

  • Sleeps 5
  • Regret no pets
  • Changeover Sat

7 nights from £526

3 bedroom apartment with sea views in Mevagissey, South Cornwall.


You can indeed see the harbour lights from this immaculate cliffside apartment set above bustling Mevagissey harbour, and watch the fishing fleet as they come and go. This ancient,...

  • Sleeps 5
  • Regret no pets
  • Changeover Sat

7 nights from £526

View
  • 20% off

    6 Apr 2019 - 13 Apr 2019

    £703.53 £562.82

Our guests rate us 4.8/5 on Feefo, the independent review site.

  • Sleeps 5 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £529

3 bedroom cottage with sea views near Lostwithiel, South Cornwall.


Set in the creekside village of Lerryn, considered to be one of the prettiest villages in Cornwall, Tanglewood is a very special holiday home in a truly magical setting. It sits in...

  • Sleeps 5 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £529

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

7 nights from £549

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


This charming bungalow, painted blue and white, commands fabulous panoramic sea views over St Mawes harbour, the Percuil river and also towards St Anthony headland and the wide ope...

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

7 nights from £549

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