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 707 cottages that sleep 5 people
7 nights from £638
Pheasant Rise
4936Spacious 3 bedroom, dog friendly barn conversion near Lanhydrock, North Cornwall.
Gather family and friends to enjoy a special break at Pheasant Rise, an immaculate countryside retreat with gorgeous welcoming interiors, open plan living and it's dog-friendly too...
7 nights from £638
7 nights from £638
Eeyore's Cottage
29493 bedroom, rural self catering cottage near Dartmouth, South Devon.
Eeyore's Cottage, once owned by Christopher Robin Milne, the son of Winnie the Pooh author A A Milne, has been beautifully restored. Found in the hamlet of Embridge, it is a 15 min...
7 nights from £638
7 nights from £640
The Old Post Office
57053 bedroom, dog friendly self catering cottage near Thirsk.
Nestled in the picturesque village of Helperby near Thirsk, set in the Howardian Hills, this charming three bedroom dog-friendly cottage with hot tub, which was once the old Post O...
7 nights from £640
7 nights from £642
Old Quay Cottage
22643 bedroom holiday cottage near Fowey, South Cornwall.
Lostwithiel is the ancient capital of Cornwall, full of history with an enchanting mix of stone buildings, antiques shops and independent retailers. Old Quay Cottage is a sympathet...
7 nights from £642
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 £644
Penally Cottage
17884 bedroom holiday cottage near the sea in Boscastle, North Cornwall.
Anyone with a romantic yearning for a harbourside haven will be thrilled with Penally Cottage. Full of character (with the occasional low beam!), this end of terrace cottage wi...
7 nights from £644
7 nights from £644
Chyandour
39663 bedroom, dog friendly cottage with sea views near St Mawes.
There are fabulous views over the sailing waters around St Mawes from both the garden and first floor living-room of this contemporary eco-house, set on the edge of St Just in Rose...
7 nights from £644
7 nights from £644
Creek View
49403 bedroom cottage with sea views near St Mawes, South Cornwall.
Reputed to be one of the prettiest villages in England (and not without good reason), St Just in Roseland is a beautiful hamlet on the gorgeous Roseland peninsula. Here you will fi...
7 nights from £644
7 nights from £644
Trevow
31733 bedroom rural cottage near Portscatho, South Cornwall.
Trevow is idyllically situated facing eastwards over fields towards the sea at Rosevine, only five minutes' walk from the National Trust coastal path and sandy beach at Porthcurnic...
7 nights from £644
7 nights from £645
Bay Tree Cottage
48353 bedroom, dog friendly cottage near Bridport, Dorset.
Situated in a sleepy west Dorset village, just a short drive from the spectacular Jurassic Coast, you will find this pretty terraced cottage. Bay Tree Cottage offers all the deligh...
7 nights from £645
7 nights from £650
Hillside
54803 bedroom, dog friendly cottage near the beach in Crantock, Cornwall.
Crantock is an utterly charming village on the north Cornwall coast with thatched cottages, a village green, two pubs and a truly fantastic beach. This is a wonderful location for ...
7 nights from £650
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