Holiday Cottages for 5 People

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. 

Our exclusive ferry discounts will make your island trip with Classic plain sailing.

We have 707 cottages that sleep 5 people

Sea Blue House is a 4 bedroom, dog friendly holiday cottage near the beach in Tenby.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £800

Sea Blue House

4811

4 bedroom, dog friendly holiday cottage near the beach in Tenby.


Step out of this very stylish townhouse and gaze at the mesmerising sea, it's literally a minute from the doorstep. Set in a quiet street, yet a short stroll from the heart of the ...

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

7 nights from £800

Happy Place (Dedwyddfa) is a 4 bedroom, dog friendly cottage with sea views near St Davids.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £802

Happy Place (Dedwyddfa)

4929

4 bedroom, dog friendly cottage with sea views near St Davids.


A 4 star Visit Wales graded property with spectacular sea views, you will find this treasure of a traditional beamed Pembrokeshire cottage nestling at the end of a quiet lane. Bein...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £802

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

Frenchman's Creek is a 3 bedroom self catering cottage near Falmouth, West Cornwall.
  • Sleeps 8 + cot
  • No pets
  • Changeover Sun

7 nights from £805

Frenchman's Creek

3344

3 bedroom self catering cottage near Falmouth, West Cornwall.


This fabulous retreat is located in the grounds of the four star Budock Vean Hotel and is named after the romantic novel by Daphne Du Maurier. With stunning views across the 9 h...

  • Sleeps 8 + cot
  • No pets
  • Changeover Sun

7 nights from £805

Octopus House is a 4 bedroom holiday cottage near the beach in St Mawes, South Cornwall.
  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £811

Octopus House

4913

4 bedroom holiday cottage near the beach in St Mawes, South Cornwall.


Octopus House is a gorgeous contemporary holiday home, perfectly situated in beautiful unspoilt St Mawes on the Roseland peninsula, just a short stroll from the bustling harbour an...

  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £811

Poldue House is a 4 bedroom, rural holiday cottage near Port Isaac, North Cornwall.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £832

Poldue House

2365

4 bedroom, rural holiday cottage near Port Isaac, North Cornwall.


Poldue House is a stunning detached house set in an Area of Outstanding Natural Beauty at the foothills of Rough Tor, (Cornwall's second highest peak and pronounced ROW-tor) close ...

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

7 nights from £832

House of Logs is a 4 bedroom, rural self catering cottage near the beach in Totland, Isle of Wight
  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £833

House of Logs

4225

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


House of Logs is a unique and stunning property located on the west coast of the Island, just a short walk from Widdick Chine and Totland Bay. Perfect for a peaceful holiday and do...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £833

September Cottage is a 4 bedroom cottage with sea views in Portscatho, South Cornwall.
  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £834

September Cottage

5161

4 bedroom cottage with sea views in Portscatho, South Cornwall.


Welcome to September Cottage, a beautifully designed, contemporary holiday abode, set in a peaceful location on the outskirts of the charming harbourside village of Portscatho on t...

  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £834

Wallis Barn is a 4 bedroom holiday cottage with sea views near Mullion, West Cornwall.
  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £838

Wallis Barn

1655

4 bedroom holiday cottage with sea views near Mullion, West Cornwall.


Wallis Barn is a splendid barn conversion with its own enclosed garden and a tennis lawn for guests’ exclusive use, (available Easter to October), so bring your own rackets or use ...

  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £838

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

Sunday House East is a 4 bedroom, dog friendly cottage near the beach near Gerrans.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £848

Sunday House East

3164

4 bedroom, dog friendly cottage near the beach near Gerrans.


Once a village chapel, Sunday House East is a gorgeous property converted from part of the original building and set in the centre of the village of Gerrans, just a short walk from...

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

7 nights from £848

Garsdon is a 4 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £852

Garsdon

3604

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


This lovely bright and spacious detached house located on a quiet lane in Seaview is just a ten minute stroll from the beautiful beach at Seagrove Bay. With a charming large enclos...

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

7 nights from £852

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