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 617 cottages that sleep 5 people

5 bedroom, dog friendly cottage near Falmouth, South Cornwall.


Oh my, what a lovely family home this is! From the approach through the dappled lanes flanked with moss-covered trees to the fabulous countryside views, and the spacious living acc...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £1100 - £2751

20% off for parties up to 4 + cot on selected dates.

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


This stunning converted coach house, benefitting from a fabulous location within the grounds of the Priory Estate, is an exceptional holiday home-from-home. The Priory Coach House ...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £1129 - £2760

Our property managers are local experts who handpick perfect places to stay.

5 bedroom, rural self catering cottage near Bodmin, North Cornwall.


How do we begin to eulogise about Lavethan Mill? Should we start with the location, the privacy, or the loving restoration and exemplary standard of furnishing in this award-winnin...

  • Sleeps 10 + 2 cots
  • Regret no pets
  • Changeover Sun

Price per week £1155 - £3570

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


A wonderfully modern property, beautifully furnished and housed in an American-style cladded exterior, Pitt Corner is roomy, with plenty of space for the family to spread out. As w...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

Price per week £1244 - £2590

5 bedroom, rural cottage near the beach near Falmouth, Cornwall.


How amazing is this? An open-air pool, a bubbling hot tub that catches the last rays of the evening sun and undulating countryside views, all just a stroll from the gorgeous Helfor...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Sat

Price per week £1350 - £3795

5 bedroom, dog friendly cottage with sea views near Port Isaac.


Wow, Upton Mill is stunning! Perched on the north Cornish coast just minutes from dog-friendly Trebarwith Strand and within easy reach of Port Isaac and Padstow, this is a perfect ...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Thu

Price per week £1360 - £3400

5 bedroom, rural self catering cottage near Fowey, South Cornwall.


What a superb family get-together house this is, seamlessly mixing the ecclesiastical soberness of the original Victorian stone-built chapel with a stunning modern glass-walled, se...

  • Sleeps 10 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £1377 - £2994

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


A truly amazing, contemporary home with views directly out to sea, in the popular sailing town of Cowes. Offering exceptional quality throughout the whole home this is a superb bas...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £1578 - £2885

We’ve been raising the standards of self catering holidays since 1977.

5 bedroom thatched, dog-friendly cottage near Honiton, South Devon.


Middle Weaver Farm is a superbly renovated detached Devon longhouse surrounded by its own extensive enclosed gardens, with an eight-seater hot tub for grown-ups, a games-room and o...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £1610 - £3500

4 bedroom holiday cottage with sea views in Kingsbridge, South Devon.


Sunnynook is a true beachside retreat, boasting the most incredible, unrivalled sea and beach views over Bigbury-on-Sea, Bantham and Burgh Island. This wonderful home also has a fa...

  • Sleeps 10 + 2 cots
  • Regret no pets
  • Changeover Fri

Price per week £1914 - £5496

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