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

Tap Cottage is a 3 bedroom, dog friendly cottage in the heart of Stockbridge and close to Winchester
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1788

Tap Cottage

5417

3 bedroom, dog friendly cottage in the heart of Stockbridge and close to Winchester


Within the bustling village of Stockbridge, this contemporary cottage has been renovated to an exceptional standard. There is so much to explore locally; with sites such as Salisbu...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1788

Moss Farmhouse is a 5 bedroom, dog friendly holiday home near Bodmin, North Cornwall.
  • Sleeps 11 + 4 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1904 *

Moss Farmhouse

4776

5 bedroom, dog friendly holiday home near Bodmin, North Cornwall.


Wow! How do we even begin to describe the magic of Moss Farmhouse? This very special, impeccably styled home is absolutely perfect for gathering family and friends together for a t...

  • Sleeps 11 + 4 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1904 *

We are Gold accredited with the Green Tourism Business Scheme.

The Hollies is a 5 bedroom self catering cottage near the beach in Windermere.
  • Sleeps 10 + cot
  • No pets
  • Changeover Fri

7 nights from £1913 *

The Hollies

5409

5 bedroom self catering cottage near the beach in Windermere.


Welcome to The Hollies, a beautiful and super stylish home ideally situated between the picturesque town of Windermere and its neighbour, Bowness on Windermere. Perfect for a littl...

  • Sleeps 10 + cot
  • No pets
  • Changeover Fri

7 nights from £1913 *

The Apple Store is a 6 bedroom, dog friendly holiday home near Newquay, North Cornwall.
  • Sleeps 12 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1948 *

The Apple Store

5714

6 bedroom, dog friendly holiday home near Newquay, North Cornwall.


Part of the glorious Tresillian Estate, this gorgeous homestay is set in secluded grounds and gardens, surrounded by Cornish countryside. With a huge open plan living space, en sui...

  • Sleeps 12 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1948 *

Flackstead is a 3 bedroom self catering cottage near the beach in Brook, Isle of Wight
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2186

Flackstead

3913

3 bedroom self catering cottage near the beach in Brook, Isle of Wight


Flackstead is a unique eco-friendly house which has breathtaking and uninterrupted coastal views across Compton Bay towards the Needles. Flackstead combines the very best of co...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2186

Tregye Farm is a 7 bedroom dog friendly self catering home near Truro, South Cornwall.
  • Sleeps 16 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £2357

Tregye Farm

4455

7 bedroom dog friendly self catering home near Truro, South Cornwall.


The ultimate luxury getaway set in an idyllic and peaceful hamlet, this stunning property really has the wow factor. This gorgeous converted barn is in an acre of private garden an...

  • Sleeps 16 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £2357

Koes Cabin is a Woodland eco cabin near the North Coast of Cornwall
  • Sleeps 6
  • No pets
  • Changeover Fri

From £350 per night

Koes Cabin

5720

Woodland eco cabin near the North Coast of Cornwall


If you're searching for a tranquil, off-grid escape close to the Cornish coastline, Koes Cabin is just the place. Koes, meaning woodland in Cornish, is nestled within a magical 43-...

  • Sleeps 6
  • No pets
  • Changeover Fri

From £350 per night

Thalassa is a 3 bedroom, dog friendly apartment with sea views near Braunton.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

From £375 per night

Thalassa

5643

3 bedroom, dog friendly apartment with sea views near Braunton.


Majestically positioned with unrivalled views of Saunton Sands beach on the north coast of Devon, this delightful apartment offers style and comfort throughout, creating the perfec...

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

From £375 per night

Choose our flexible booking option and have the ability to cancel anytime.

Bombora is a 3 bedroom, dog friendly apartment with sea views near Braunton, Devon.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

From £375 per night

Bombora

5641

3 bedroom, dog friendly apartment with sea views near Braunton, Devon.


Majestically positioned in a prime coastal position on the dramatic north Devon coast and overlooking picture perfect Saunton Sands beach, you have found this rather special dog-fr...

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

From £375 per night

Sands View is a 3 bedroom apartment with sea views near Braunton, North Devon.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

From £530 per night

Sands View

5538

3 bedroom apartment with sea views near Braunton, North Devon.


Offering a prime position with a view of the golden sands of Saunton Sands beach and the rather dramatic Atlantic Ocean on the north Devon coast you will discover the luxury of San...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

From £530 per night

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