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. 

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 626 cottages that sleep 5 people

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

Price per week £481 - £1050

3 bedroom holiday cottage near the beach in Rock, North Cornwall.


Rock is a very special destination and, coupled with the comfort and deceptively spacious interior of this charming Cornish terraced cottage, guests are assured a wonderful holiday...

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

Price per week £482 - £1320

Don’t miss out; reserve your favourite 2019 holiday cottage for just £30

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 ten minutes' drive from the pre...

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

Price per week £484 - £1210

3 bedroom holiday cottage near Totnes, South Devon.


Found in the village of Marldon, only a short distance from Totnes and the glorious Devon coast, this very comfortable cottage is furnished with real flair and style. Wisteria ...

  • Sleeps 5
  • Regret no pets
  • Changeover Fri

Price per week £488 - £1220

3 bedroom holiday cottage near the beach in Mullion, West Cornwall.


The pretty village of Mullion is the largest on the Lizard, with shops, pubs and restaurants clustering around the 15th Century church of St Mellanus which lies at its heart. Locat...

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

Price per week £488 - £1220

3 bedroom, dog friendly cottage near the beach near Boscastle.


Pollywinky Cottage is a traditional terraced cottage, situated in the sleepy hamlet of Treknow perched high on Cornwall's breathtaking north coast. Only a few minutes from your doo...

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

Price per week £490 - £1065

3 bedroom self catering cottage in Wareham, Dorset.


Wareham is the gateway to the Jurassic Coast, a fabulous base from which to explore the Isle of Purbeck. Just within the ancient Saxon walls of this historic market town, Northgate...

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

Price per week £493 - £995

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

Price per week £495 - £1050

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

3 bedroom self catering cottage in Newport, Isle of Wight


Located in the centre of the Island on the outskirts of the town of Newport, this is perfectly located to explore different places on the Isle of Wight. In the colder months, wrap ...

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

Price per week £495 - £1415

Shepherds Hut sleeping 5, dog friendly near Tiverton, North Devon.


Shepherd's Sky Super Hut is truly unique. This huge shepherd's hut, measuring 36' long, has been lovingly treated to a bespoke make-over, and offers two bedrooms at either end whic...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £497 - £894

30% off for parties up to 2 + cot on selected dates. Only one bedroom is available at the discounted rate.

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