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 557 cottages that sleep 5 people

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1134

4 bedroom, dog friendly cottage near the beach in Branscombe, Devon.


Set in its own mature gardens on a south-facing hillside, Barnell Cottage has views over Branscombe Vale and out to the World Heritage Jurassic Coast at Branscombe mouth. This beau...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1134

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1151

4 bedroom thatched, dog-friendly cottage near South Molton, Devon.


Hidden deep in the truly peaceful, unspoilt north Devon countryside, in the grounds of an historic castle, lies Affeton Barton; a 16th Century farmhouse, newly renovated to a very ...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1151

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

7 nights from £1200

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


A spectacular waterfront three-storey house situated on Seaview duver with uninterrupted sea views from the kitchen/dining-room and the first floor balcony. Just a few steps from y...

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

7 nights from £1200

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

7 nights from £1250

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


This absolutely stunning barn conversion is a little slice of luxury just outside the village of St Helens, only a short stroll to the St Helens Duver, sand dunes, beach and the Ba...

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

7 nights from £1250

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

7 nights from £1375

4 bedroom, rural self catering cottage near the beach in Yarmouth, Isle of Wight


This beautiful house is set in several acres of garden on the outskirts of Yarmouth, just a few minutes walk to the water’s edge, a truly stunning holiday destination. The property...

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

7 nights from £1375

  • Sleeps 9 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £646

5 bedroom self catering cottage near the beach in Ryde, Isle of Wight.


Middle Lodge is a beautiful 1860s, stone-built, Victorian holiday home set in a mature enclosed garden on the edge of Ryde on the near-east side of the Island. It would be ideal f...

  • Sleeps 9 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £646

View
  • 10% off

    23 Feb 2019 - 2 Mar 2019

    £718.06 £646.25

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

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £660

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


6 Seafield Terrace is a charming, spacious terraced cottage set in the pretty village of Seaview. It would ideally suit a large family, several couples or a group of friends travel...

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £660

  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £726

5 bedroom, dog friendly self catering cottage near Bridport, Dorset.


This beautiful stone farmhouse has something very special indeed – it comes with a 450 acre wildlife and nature reserve and a unique relationship with Dorset Wildlife Trust. Quite ...

  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £726

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £760

5 bedroom, dog-friendly cottage near Mevagissey, South Cornwall.


This fabulous holiday house is beautifully furnished and superbly well-equipped, and provides plenty of space for everyone to spread out. With a bubbling hot tub in the garden-room...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £760

View
  • 20% off

    23 Feb 2019 - 2 Mar 2019

    £949.62 £759.70

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £810

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


2 Little Cedars is a sleek and modern property, with a light and clean finish throughout. Split over three floors, and stylishly decorated with luxury furnishings, this delightful ...

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £810

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