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 £774
Aveton Cottage
23553 bedroom, rural holiday cottage with a pool near Totnes, South Devon.
In a tranquil Devonshire valley, this gorgeous stone cottage has sunlight streaming in through glazed doors and floor length windows. Approached by a farm lane, past Aveton Farmhou...
7 nights from £774
7 nights from £775
Beggars Roost
43463 bedroom self catering apartment with sea views in Seaview, Isle of Wight
This gorgeous first floor apartment in the heart of Seaview village is perfectly placed to reach everything within a few minutes' walk. The seafront is just around the corner, a po...
7 nights from £775
7 nights from £777
Longdown Hall
43863 bedroom self catering cottage with sea views in Ventnor, Isle of Wight
A stunning property in Ventnor on the southern tip of the Island, with the most sensational 180 degree sea views from the sun-drenched patio. Relax with your breakfast in the sunsh...
7 nights from £777
7 nights from £777
Trewane Cottage
2333 bedroom, dog friendly cottage near Port Isaac, North Cornwall.
Set in an idyllic country estate, Trewane Cottage is a detached, 17th Century, beautifully-styled retreat and the ideal place to recharge your batteries. The gorgeous kitchen/break...
7 nights from £777
7 nights from £778
The Willows
37323 bedroom, dog friendly cottage near the beach in Westward Ho!.
This exceptional, purpose-built property is an absolute treat, a family-sized holiday home moments from the Blue Flag sandy beach at Westward Ho! on the north Devon coast. Outside ...
7 nights from £778
7 nights from £779
Miranda Cottage
40463 bedroom, dog friendly holiday cottage near Helford, West Cornwall.
Miranda Cottage is a quintessential Cornish thatched cottage in the heart of the village of St Martin, a short distance from the famous sailing waters of the Helford River. Bea...
7 nights from £779
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 £779
Whim Cottage
53533 bedroom, dog friendly cottage near the beach near Falmouth.
Situated in an enviable and unspoilt Area of Outstanding Natural Beauty (now known as National Landscapes) between Mylor Bridge and Restronguet Creek, this stunning Grade II Listed...
7 nights from £779
7 nights from £779
The Old Byre
29813 bedroom, dog friendly cottage with hot tub in Widemouth Bay, North Cornwall.
The Old Byre is a single-storey, 19th Century barn converted into a lovely home-from-home with an enclosed garden, bubbling hot tub and close to the shores of Widemouth Bay. Luxuri...
7 nights from £779
7 nights from £779 *
Garretts
53415 bedroom, dog friendly cottage near the beach in Kingsand, Cornwall.
Set in the heart of the magical twinned villages of Kingsand and Cawsand, on the breathtaking Rame peninsula, this lovingly presented Grade II Listed cottage is within walking dist...
7 nights from £779 *
7 nights from £780
The Drey
51393 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Located in the grand building that is Springfield Court, guests staying in this lovely holiday home can take full enjoyment of the grounds during their stay. Comfortably furnished ...
7 nights from £780
