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 holiday cottage near the beach in Seaview, Isle of Wight.


6 Tollgate Cottages is a bright and cheery cottage set in a small, gated development near the pretty village of Seaview. Close to the beach, local shops and bars, and with Cafe Blu...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £375 - £830

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


10 Tollgate Cottages is a pastel coloured, beach bungalow set in a small gated development close to the waterfront. Clean, neutral decor and its close proximity to the beach make t...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £375 - £830

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


24 Tollgate Cottages is a comfortable property just a stone's throw away from the beach, and a short walk from the local shops and dining in Seaview village. Situated on a small de...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £375 - £830

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


27 Tollgate Cottages is one of a number of well presented, beachfront holiday bungalows situated in Salterns Village, a small gated development located opposite Seaview Duver and b...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £375 - £830

3 bedroom, dog friendly cottage near the beach in Portscatho.


This light and bright ground floor apartment is quietly situated just above the square in the charming village of Portscatho and only minutes from the harbour and stunning Gerrans ...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £380 - £961

2 bedroom, dog friendly holiday cottage near the beach in Shanklin, Isle of Wight


This modern and bright bungalow with a south-facing garden is perfect for a family holiday and as it has a fully-enclosed rear garden, why not bring your four-legged friends? Sleep...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £384 - £850

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

3 bedroom self catering cottage near the beach near Portscatho.


This spacious first floor apartment is in the very heart of this lovely coastal village, with two tempting art galleries below it, the picturesque harbour with its fishing boats an...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

Price per week £387 - £910

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


Delightful Grascott Cottage exudes warmth and welcome, from the hand-made kitchen to the cosy living area with beech floors, into the sunny conservatory and to the bedrooms upstair...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £392 - £980

3 bedroom, dog friendly holiday cottage with hot tub in Beaworthy, North Devon.


Imagine yourself slinking back into a bubbling hot tub and gazing out over the beautiful rolling countryside whilst the younger members of the group play merrily within your enclos...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

Price per week £396 - £1089

4 bedroom self catering cottage near Bovey Tracey, Dartmoor.


Nestled in the picture perfect village of Ilsington on the eastern edge of Dartmoor, The Old Post Office is perfectly located and exceptionally furnished making this cottage a real...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

Price per week £396 - £1085

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