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.
We have 633 cottages that sleep 5 people
7 nights from £418
Bay Cottage
25613 bedroom, dog friendly apartment with sea views, Shaldon.
Bay Cottage is just steps from the beach in Shaldon, which lines the south shore of the Teign estuary. The South West Coast Path is on the doorstep, so this is a fantastic place fo...
7 nights from £418
7 nights from £504
Smugglers Cottage
32183 bedroom, dog friendly cottage near the beach in Branscombe, Devon.
Smugglers Cottage is in a perfect location just one mile inland from the stunning Jurassic Coast, not far from the Devon/Dorset border on the outskirts of the beautiful east Devon ...
7 nights from £504
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £506
Tolpuddle Cottage
37523 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.
This pretty thatched cottage is in the tranquil historic village of Tolpuddle, just 15 miles from the World Heritage Jurassic Coast. An ideal base for a family holiday or perfect f...
7 nights from £506
7 nights from £303
Higher Yellands Cottage
39973 bedroom, rural holiday cottage near Ottery St Mary, South Devon.
This cheerful cottage is close to the east Devon village of Whimple, between Honiton and Exeter. It is a pretty and peaceful rural area surrounded by traditional apple orchards and...
7 nights from £303
7 nights from £317
Red House
36482 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
A deceptively spacious semi-detached Victorian property, Red House has a lovely large kitchen with both a breakfast-bar and a separate dining-area from which the enclosed garden ca...
7 nights from £317
7 nights from £341
Oaks
36392 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
A Victorian property set on a quiet road and yards from the beach. Oaks is a well-equipped property, decorated to a high standard and perfect for families with open plan seating an...
7 nights from £341
7 nights from £344
1 The Saltings
35103 bedroom self catering apartment near the beach in Seaview Isle of Wight.
1 The Saltings is a three-bedroom, lower ground floor apartment boasting a lovely beachfront location. It would ideally suit a family with children keen to enjoy the delights of th...
7 nights from £344
7 nights from £346
Moonbeam
41353 bedroom, rural holiday apartment near Marazion, West Cornwall.
The views from Moonbeam, across the countryside to St Michael's Mount and Mount's Bay, are wonderful. Relax on the south-facing balcony, wine in hand and enjoy the sound of silence...
7 nights from £346
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
7 nights from £359
Spring Tide
36602 bedroom self catering cottage at Island Harbour, near Newport.
Spring Tide is a delightful holiday cottage situated in a small development at Island Harbour Marina on the banks of the River Medina. The marina is set in a beautiful secluded val...
7 nights from £359
7 nights from £361
Atlas Cottage
28693 bedroom self catering cottage in Buckfastleigh, Dartmoor.
An old weaver's cottage, dating back to early 1703 and Grade II Listed, Atlas Cottage is lovely and has low lintels and exposed beams as well as the original twisting wooden stairc...
7 nights from £361