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

6 Seafield Terrace is a 5 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1030

6 Seafield Terrace

3562

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


6 Seafield Terrace is a charming, spacious terraced cottage set in the pretty village of Seaview. It would ideally suit a large family, several couples or a group of friends travel...

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1030

Beech Cottage is a 5 bedroom, dog friendly cottage with views over the nature reserve near Bridport, Dorset.
  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1080

Beech Cottage

2887

5 bedroom, dog friendly cottage with views over the nature reserve near Bridport, Dorset.


This beautiful stone farmhouse has something very special indeed - it comes with a 450 acre nature reserve and a unique relationship with Dorset Wildlife Trust, offering comfortabl...

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

7 nights from £1080

Creekside is a 4 bedroom, dog friendly holiday cottage with sea views in Wootton, Isle of Wight.
  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1157

Creekside

3588

4 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 9 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1157

2 Little Cedars is a 4 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1228

2 Little Cedars

3520

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


2 Little Cedars is a sleek and modern property, with a light and clean finish throughout. Split over three floors, and stylishly decorated with luxury furnishings, this delightful ...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1228

View
  • 20% off

    20 Dec 2024 - 27 Dec 2024

    £2292.00 £1833.60

  • 20% off

    27 Dec 2024 - 3 Jan 2025

    £2292.00 £1833.60

Luffs Farm is a 5 bedroom, dog friendly self catering cottage near Battle.
  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1295

Luffs Farm

5653

5 bedroom, dog friendly self catering cottage near Battle.


This delightful farmhouse situated in 1066 country, has views over the valley towards the village of Sedlescombe. It makes an excellent retreat for families and friends looking for...

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

7 nights from £1295

Rose on the Cliff is a 4 bedroom, dog friendly cottage with sea views near Helford.
  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1446

Rose on the Cliff

5120

4 bedroom, dog friendly cottage with sea views near Helford.


A spectacular retreat perched on the picturesque banks of Gillan Creek. Tucked away down a private unmade lane, this unique spot is really very special and only shared with a handf...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1446

We are Gold accredited with the Green Tourism Business Scheme.

Brockhill Chapel is a 5 bedroom cottage with sea views in Crackington Haven, Cornwall.
  • Sleeps 10 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £

Brockhill Chapel

5766

5 bedroom cottage with sea views in Crackington Haven, Cornwall.


When location and property work in perfect harmony, it promises holiday memories that will last a lifetime and that's exactly what this gorgeous retreat will deliver! Perched high ...

  • Sleeps 10 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £

Sea View is a 5 bedroom, dog friendly holiday cottage with sea views in Fishguard.
  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £473

Sea View

4432

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


Situated perfectly in the heart of the pretty town of Fishguard, this charming terraced townhouse stands in an elevated position with glorious views over the harbour. This stunning...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £473

Grascott House is a 5 bedroom, dog friendly holiday cottage near Holsworthy, North Devon.
  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £781

Grascott House

2375

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


Make your way to the wonderfully tranquil award-winning forest and countryside, where you will find Grascott House; a magical getaway with more than 200 almost uninhabited acres to...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £781

Cormorant is a 5 bedroom, dog friendly cottage with sea views near Whitsand Bay.
  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £782

Cormorant

4549

5 bedroom, dog friendly cottage with sea views near Whitsand Bay.


Wow - what a house, what a setting, what a view!!! Looking for the ultimate excuse to gather family and friends for the perfect seaside escape? Then head down to Cormorant - it is ...

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £782

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