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 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £811

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


Rosa Monte is a semi-detached property with three double bedrooms and a children's bunk bedroom, accommodating eight in total. Situated just off Ryde esplanade it’s a short walk in...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £811

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £829

4 bedroom thatched cottage with estuary views in Shaldon.


Shaldon is a lovely village lining the banks of the River Teign with its own small sandy beach. Just a half-mile from the hub of the village itself, a conservation area, is a small...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £829

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

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £837

4 bedroom cottage with sea views near Marazion, West Cornwall.


Fancy relaxing in a hot tub, perched on the cliff top overlooking Perranuthnoe beach? Well, this one is for you! Cliff House is a warm, stylish detached retreat set high above Perr...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £837

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

7 nights from £841

4 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight


With stunning sea views from not one but two balconies Solent View Road is a wonderful holiday destination within a few minutes' walk from Seagrove Bay. Located just on the outskir...

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

7 nights from £841

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £847

4 bedroom, dog friendly cottage with sea views and hot tub near Kingsand.


Lady Emma's Cottage is one of the most stunning and exclusive retreats in the United Kingdom. The 1882 Arts and Crafts property sits framed on one side by 865 acres of Grade 1 list...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £847

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £850

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


This completely refurbished cottage is nestled at the end of Ryde Road, just a short walk from the beach and Seaview village. With off-street parking and a lovely large garden to t...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £850

View
  • 15% off

    29 Mar 2019 - 5 Apr 2019

    £1075.03 £913.78

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £850

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


A wonderful contemporary beach house, offering accommodation for eight, within a few minutes walk to the beach and Bembridge village. There is a spacious kitchen/diner with doors o...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £850

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £852

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


Walnut Cottage is a real find if you're looking for a spot of luxury on holiday. Tucked away in central Seaview village Walnut offers spacious accommodation over two floors and an ...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £852

View
  • 20% off

    5 Apr 2019 - 12 Apr 2019

    £1524.96 £1219.97

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

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Sun

7 nights from £860

4 bedroom, dog friendly cottage with sea views in St Ives, Cornwall.


Step outside the sitting-room onto the magnificent decked terrace – take in the fabulous sea views stretching from Hayle Towans to beyond Godrevy Lighthouse. A spacious, contempora...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Sun

7 nights from £860

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

7 nights from £867

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


Tides Reach is a wonderful, newly modernised family house along the Seaview Duver just a short walk into Seaview Village and the Yacht Club. Tides Reach has a stylish open plan sit...

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

7 nights from £867

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