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 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

Price per week £809 - £2499

5 bedroom, dog friendly holiday cottage with sea views in Ventnor.


Woodlands offers a perfect retreat for friends and family to spend quality time together in a stunning Grade II listed Victorian villa in the cosmopolitan town of Ventnor. With amp...

  • Sleeps 9 + 3 cots
  • Dogs welcome
  • Changeover Fri

Price per week £813 - £2350

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


The Old Boat House is an attractive period cottage set in a fantastic waterfront location on the edge of the beach at Seagrove Bay. This is a charming family home and can be rented...

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

Price per week £931 - £2360

View
  • 15% off

    20 Jul 2018 - 27 Jul 2018

    £2360.00 £2006.00

  • 15% off

    3 Aug 2018 - 10 Aug 2018

    £2360.00 £2006.00

dog friendly holiday cottages near Tavistock, Dartmoor.


For years the Owner and her children went on holiday with her parents, siblings and their children. Great fun and a host of memories but for everyone to remain sane they each had t...

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

Price per week £1062 - £2199

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

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


Barton Manor Farmhouse is a beautifully refurbished, 150 year old property set in the delightful grounds of the Barton Estate, adjacent to English Heritage's Osborne House, former ...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £1277 - £3120

View
  • 15% off

    3 Aug 2018 - 10 Aug 2018

    £3120.00 £2652.00

5 bedroom, rural cottage with sea views near Falmouth, Cornwall.


For unparalleled views over Port Navas Creek and complete peace and tranquility in an idyllic setting, Gate Acre is pretty hard to beat. Perfect for family holidays in any season t...

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

Price per week £1399 - £2640

5 bedroom, dog friendly holiday cottage near Holsworthy, North Devon.


The award-winning forest and countryside around Grascott House is magical: more than 200 almost uninhabited acres including woodland, wildflower meadows and three small, trout-stoc...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £653 - £1790

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


Orchard House is a wonderful property for an extended family looking for a sprawling holiday home near the beach in Bembridge. The downstairs living areas are inviting - no doubt t...

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

Price per week £717 - £1928

5 bedroom, dog friendly holiday cottage with sea views in Wootton, Isle of Wight.


Creekside is a fabulous waterfront property that makes a wonderful choice of holiday home at any time of the year. This stunning detached house, set on the banks of Wootton Creek, ...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £738 - £1683

5 bedroom, rural cottage near the beach in Portscatho, Cornwall.


Tucked away at the end of a Cornish country lane, this lovely old farmhouse is set in idyllic surroundings, overlooking adjacent farmland to the sea beyond. Imaginatively restored ...

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

Price per week £821 - £2250

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

Loading more